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Vacation Rentals In Annapolis, MD

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We Have 1 Vacation Rental Offers Available In Annapolis. Average Price Per Night Is $536.59. Find Your Vacation Home Today.

  • Property-1 Image 1
    Exceptional
    (6)
    Private Vacation Home
    2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
    Annapolis, Maryland, United States

    Harrison HallbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrLooking for the perfect retreat for a memorable stay-cation with your beloved groups? Then, look no further than this two-story, family-friendly home located just a mile from the heart of the forever charming Annapolis! The extensive enclosed backyard provides a private space where you and your guests can hang out and create everlasting memories - gather around the firepit under the starry night sky or host a warm-weather barbecue on the deck, equipped with a propane grill, a six-person dining table, and a cushy swing. brbrUpon entering the first floor of this darling home, guests will first come across a beautifully appointed foyer with vintage music-scene decor. As you continue the tour, an astonishing dining room will appear before your eyes. This space is furnished with a large eight-person dining table. The tiled open kitchen will be a chef's delight. It has stainless steel appliances, including a double-door fridge, stove, oven, dishwasher, drip coffee maker, and microwave. Additional highlights include an elegant wet bar, a wine section, and a breakfast bar that seats three. The adjoining and spacious living room has been equipped with comfortable sofas, a three-piece coffee table set with a chess board, a stone floor-to-ceiling gas fireplace, and a gigantic smart TV with streaming services and a soundbar. brbrAll four bedrooms and a laundry room are upstairs. The carpeted main bedroom offers a comfortable bed and an en suite bathroom with a stand-alone shower with a tiled bench, a soaking tub, and double vanity.brbrTHINGS TO KNOWbrbrParking notes: There is free parking available for 2 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the "Rental Agreement" on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.brbrCity/town permit number: STR22-145124 Read More

    4 Bed
    3 Baths
    Sleeps 8
    $591 / Nightly
  • Property-2 Image 1
    Wonderful
    (34)
    Private Vacation Home
    Naval Academy Themed at the Gates with PARKING!
    Annapolis, Maryland, United States

    Welcome to this gorgeous 1900's fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 cars. Owned by 4 Naval Academy graduates - 3 U.S. Marines and one Navy nuclear surface warfare officer - this home is a tribute to the loyal bond they created in the 14th company at the Academy and continue to share after 10+ years they have served our country. You will feel that energy the moment you pull into the home.brbrLocated on one of the prettiest streets in Annapolis, less than one block from the main entrance to Naval Academy, the front porch will welcome you and provide the perfect place to watch the energy of downtown Historic Annapolis. Next is the enclosed front hallway opening to the stunning Great Room complete with entertainment bar and dining area. Soak in the classic Naval Academy-themed decor while enjoying the large open spaces and bedrooms for up to 11 guests. The large gourmet kitchen features additional seating at the breakfast bar - perfect for gathering in the morning before heading out to see the local sights. The second level features 3 large bedrooms and the top level features a stunning extra large bedroom and sitting room for 5. brbrJust steps from all Annapolis has to offer, this home is wonderful for families and friends coming in for that special Naval Academy or boat show event, or wanting to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops right around the corner! brbr**COVID - 19 Extra Special Precautions: Our guests' and staff's health is our top priority. Our cleaners are taking every precaution when cleaning this home and making sure it meets CDC standards. We are going above and beyond to ensure all surfaces and touch points are being cleaned thoroughly and disinfected (including all light switches, faucets, doorknobs, cabinet handles, remotes, etc.). You will have self check-in and no physical interaction with anyone.**brbr**Ask us about weekday stays with no minimum-stay requirements!brbrSLEEPING ARRANGEMENTS 4 BR / 2 BA / Sleeps 11: brMain Bedroom 1: br- Second Floorbr- Queen Size Bed brbrMain Bedroom 2: br- Second Floorbr- Queen Size Bed brbrGuest Bedroom: br-Second Floorbr-Two twin bedsbrbr3rd Floor Room: br- Open Living and sleeping spacebr- 5 Twin BedsbrbrHIGHLIGHTS:br- Front Porch with sitting area with new furniturebr- Custom Full Bar seats 4-5br- Spacious gourmet kitchenbr- Eat-in kitchen counter seats 4br- Dining room table seats 6-8br- WiFi br- Big Screen Smart TV'sbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service br- Parking for 2 carsbr- Washer & dryer located inside the homebr- Baby Crib (Pack-nPlay) and stroller available upon requestbr- Non-Smoking br- No petsbr- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations.br- Keyless entry. Drive straight to your rental home and enter the back door with an electronic lock code. Prior to your visit, we will send you our mobile app with directions and full instructions.br***************brProperty Distance to: br- U.S. Naval Academy – 1 block br- Washington, DC – 30 miles br- Baltimore - 25 milesbr***************br* Guest Gift Basket with Wine, snacks, coffee and creamers!br* Amenity & Supplies pack, a starter set of soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.br* All beds are ready made for you with freshly laundered sheets & towels.brbrHouse RulesbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.brCheck-in time: 4:00 pmbrCheck-out time: 11:00 am Read More

    4 Bed
    2 Baths
    Sleeps 11
    $645 / Nightly
  • Property-3 Image 1
    Private Vacation Home
    Water Views - Close to Downtown Annapolis
    Annapolis, Maryland, United States

    Come enjoy an Annapolis getaway. Perfect for vacations, and enjoying the Chesapeake Bay, and Maryland's capital city only 15 minutes away. The house has views of Fishing Creek and the boat launch is at the end of the street to kayak or boat by Thomas Point, the Chesapeake Bay and have views of the Thomas Point Lighthouse. The neighborhood is quiet and friendly and is great for walks and runs. You can walk 6 blocks to a small beach or one block to the crabbing dock.brbrThis 5 bedroom home sleeps 12-14 in 3 king sized beds, 1 queen bed & a bunk room. Main bedroom upstairs with King bed, private bath, and two closets. Two King bedrooms (up and down) have ample space. Queen bedroom upstairs. Bunk bedroom sleeps 4-5 with double bunk beds. Bedrooms are comfortably furnished with beautiful new crisp linens, pillows and bed coverings. brbrDownstairs family area and dining room have water views. Plus there is a game room featuring a 50” smart tv, Golden Tee, poker chips/cards, and dart board, games and puzzles.brbrEnjoy the large backyard with a fire pit for relaxing and enjoying the evening on the bay or sit on the back deck for outside eating and views of the sunset! There is a gas grill ready for you to cook up some good eats to enjoy on the patio.brbrYour stay includes Wi-Fi, parking for 3 cars, fully stocked kitchen, and a washer/dryer.brbrLicense number STR-271 Read More

    5 Bed
    3 Baths
    Sleeps 12
    $373 / Nightly
  • Property-4 Image 1
    Wonderful
    (49)
    Private Vacation Home
    Large Contemporary in Wooded Privacy
    Annapolis, Maryland, United States

    Lovely, contemporary sitting on three and-a-half acres of wooded beauty. Lots of glass and cedar. Open and airy floor plan. Sunken living room with see-through fire place. Huge glass windows and full length deck with view of surrounding woods. All this and yet close to downtown Annapolis and the Naval Academy! PERFECT HOUSE FOR LARGE & MULTI-FAMILY ACCOMMODATIONS. A FAVORITE FOR NAVAL ACADEMY COMMISSIONING WEEK SINCE 2006!brbrKeywords: House Read More

    5 Bed
    4 Baths
    Sleeps 12
    $560 / Nightly
  • Property-5 Image 1
    Wonderful
    (12)
    Cottage
    NEW LISTING! Waterfront cottage in gated beach community w/ hot tub, pier, kayak
    Annapolis, Maryland, United States

    Come enjoy a relaxing stay in our coastal waterfront cottage in Epping Forest! Just steps from a community pier perfect for SUP's or kayaks with gorgeous water views that are stunning all year around. This home is tucked into the private gated community of Epping forest, featuring a private beach with a clubhouse, swimming area and marina. brbrThe house sleeps 6 comfortably with 3 bedrooms and 2 full bathrooms. It has great outdoor seating and entertaining space and a relaxing screened in porch with a porch swing. brbrThe property is just minutes from downtown Annapolis and the Naval Academy. Read More

    3 Bed
    2 Baths
    Sleeps 7
    $347 / Nightly
  • Property-6 Image 1
    Private Vacation Home
    421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
    Annapolis, Maryland, United States

    421 Irie brCity Of Annapolis License Number 145052brbrSkip the lines!!! I offer personal chef services!!! brbrNOTE: I ?? my neighbors!! brPLEASE Respect them!! Nbrbrhttps://www.visitannapolis.org/events/?view=list&sort=datebrbrCONTACT owner, Liz 301730100 for bookings and rates for W2024 and beyond... ?brbrOwner:brLiz [email protected] ~ to be at total peace with your current state of being.....brAKA NO WORRIES!!!!brbrThis charming, 2 story cottage was Inspired by sun-drenched island vacations and tropical shores.... ahhhh ..... The feeling of Irie!!! brbrThis 2 bedroom and 2 full bath maybe compact, (twin size Crate and Barrel sleeper Chair and Half for additional guest), BUT She SURE packs a powerful punch!! TOTALLY open concept living area, caterers (I’m a former catering company owner for 20 years, just trying to simplify my life!!) stocked kitchen for entertaining, fully fenced in professionally landscaped yard with SO many colorful flowers, herbs and vegetables for the picking, screened in porch for additional living space amongst nature, incredible flower and herb gardens, endless entertaining, morning room and yes... OFF STREET PARKING and Private FULL size .... YES... PRIVATE... pool in the heart of Eastport! brbrLocated in The Maritime Republic of Eastport, an easy going, Chill-Laxing community, 421 Irie is less then: br1 mile from Downtown Annapolis City Dock br1.2 miles from Maryland State Housebr1.3 Miles from the Navel Academy!! brbr421 IRIE offers you and your guests, up to five, everything!! Restaurant Row with over a dozen fabulous restaurants with-in a mile, small mom and pop shops, several yacht clubs and marinas, museums, and of course.... WATER Activities!! You say, you're on vacation and just want to chillax, just stay in and simply enjoy your new vacation home!!brbr421 Irie has it all!!!!!brbrStart your day off with your morning beverage from the built-in beverage and breakfast nook. Savior your authentic French pastry from our local bakery, Bakers and Co., a short stroll away. Enjoy your sweet or savory fare in the sunroom. If you must check in with work, we have an Ethan Allen secretary's desk. brbrFollowing breakfast you may choose to take a 10 minute stroll across Spa Creek Bridge to downtown Annapolis, City Dock, and the Navel Academy!! While in route, take time to admire the diverse number of power and sail boats in the numerous area marinas. ALL ... with-in a 10 minute stroll!! brbrYou say you do not feel like walking, the best kept secret, Annapolis Water Taxi picks up and drops off only a block away!!!! $4-$9!!! It will drop you off right at City Dock!! Want to try your hand at sailing or power boats??!! There are several sailing and boating schools, YES, all with-in a 10 minute stroll!!brbrOnce you return from your adventure to this amazing 2 story cottage, relax by the glistening saltwater pool in one of the sun loungers. Or take a dip to refresh and reset the mind. You do not feel like swimming?? No PROBLEM!! Enjoy an adult beverage in the new (Apr. 2023) sunroom while listening to some island music, reading a book, marveling at the flower garden, watching your family or friend enjoy the pool... brAfter all, your life is IRIE when you stay with us!!brbrP.S.brIF, you do not feel like going out to dinner or cooking, for an additional fee, there are local grab and go culinary offerings, private chefs, and curbside pickup and deliveries available. brbrContactless Concierge Service:brBeing a local, myself, I can give you a locals eye into activities and services, as well! There are quite a few adventure waiting for you, your family and friends at 421 Irie!brbrWe look forward to hosting you and your guests and making everyone’s life IRIE!!! brbrCheers!!!brLiz Hopkinson Read More

    2 Bed
    2 Baths
    Sleeps 5
    $322 / Nightly
  • Property-7 Image 1
    Private Vacation Home
    Easy Annapolis lodging - still available for Sailboat Show!
    Annapolis, Maryland, United States

    This home (divided/upper floor only) is perfect for families, situated on a quiet residential street with a gorgeous backyard with patio, grill, trampoline & swing set. Comfy living & spacious kitchen with plenty of parking. Read More

    3 Bed
    2 Baths
    Sleeps 8
    $469 / Nightly
  • Property-8 Image 1
    (29)
    Private Vacation Home
    ACROSS FROM STADIUM - walk to downtown Annapolis.
    Annapolis, Maryland, United States

    Across the street from the Navy and Marine Corps Stadium and walking distance to historic downtown Annapolis - you will be in the heart of it all! Our home is a warm and welcoming space in a park-like setting with plenty of parking and gathering spaces to enjoy with family and friends. Bringing kids? They are sure to enjoy the kid space with games, toys and art. Entertaining? Use the large yard, decks, & multiple living areas. Multiple families? Enjoy two master suites and plenty of room. brbrThe spacebrbrOur home has two master suites with king size beds as well as a large laundry room with washer, dryer, ironing board and iron. We also provide a pack n play and baby gate for the stairs.brbrGuest accessbrbrYou will have full access to the house and shed.brbrInteraction with guestsbrbrWe are not usually in the area, but we provide the numbers for cleaning staff and maintenance people that you can call if anything pops up. We are also available via phone and email if you need anything. Our goal is for you to enjoy your stay!brbrOther things to notebrbrKid friendly space! We have a kid area with toys, trains, art supplies as well as a baby gate for the stairs and a pack n play with sheets. Read More

    4 Bed
    3 Baths
    Sleeps 10
    $309 / Nightly
  • Property-9 Image 1
    Wonderful
    (14)
    Private Vacation Home
    Serene waterfront sunsets in this Annapolis home
    Annapolis, Maryland, United States

    *Flexible Commissioning Week Cancellation Policy*brbrEnjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sits on 1.5+ acres. The light-filled farmhouse is located on Persimmon Point, which is positioned between Harness Creek and the South River. It is a peninsula rich in local lore that includes native american oysters mounds, pirate hideouts, tobacco farming and world champion cows. brbrOnce the home was part of the original Wimbledon Farm. From the 1930’s, Wimbledon Farm grew abundant produce and tobacco. The last magnificent tobacco barn in Annapolis is on the property next to the house. Wimbledon was also famous for their dairy. Their dairy cows and bulls attracted breeders from around the world and famously started the “Carnation” milk herd. The dairy barn was immense and the milk came into the small milk house, which is now the charming "Milkhouse Suite". Here the milk was chilled and sent out to be bottled and delivered.brbrThe home was renovated to its current beauty by opening the entire back of the house to the water with windows and connecting the main house to the "milk house". The house offers a special, very private family retreat just minutes to downtown Annapolis. All of the living space, and 4 of the 5 bedrooms, are on the main floor. The lofted upstairs bedroom is perfect for the younger crowd and has 3 twin beds and room to enjoy each other's company. The open floor plan, deck and terrace provide multiple living spaces inside and out. There are 2 full baths and room for 12 guests to sleep comfortably. There is a large stone patio with fountain and dining tables, a pair of Adirondack chairs on the back deck under the shady wisteria pergola, and a BBQ grill. Inside, the dining table seats 8 and there’s room for 3 at the breakfast bar. Across the lush lawn, there is also a small pier on the pond for kayak launching or fishing fun for small anglers. Guests can also get away from the day by lounging on the creek side on the front porch swing. brbrLocal activities include, Great Frogs Winery (less than ½ mile away down the street), Quiet Waters Park (across the creek with hiking trails, ice skating and SUP rentals) and kayaking or biking. The home is a wonderful place to relax for families and friends coming in for Naval Academy events, boat shows, wine tasting or just a beautiful getaway.brbr**COVID - 19 Extra Special Precautions: Our guests' and staff's health is our top priority. Our cleaners are taking every precaution when cleaning this home and making sure they meet CDC standards. We are going above and beyond to ensure all surfaces and touch points are being cleaned thoroughly and disinfected (including all light switches, faucets, doorknobs, cabinet handles, remotes, etc.). brbrSLEEPING ARRANGEMENTS 5 BR / 2 BA / Sleeps 10 adults (2 children): brMilk House Suite: br-Main Floorbr-Queen Bed br-Living room with Full sofa sleeperbr-Private en-suite bathroom large tile showerbr-Private entrance and water viewsbrbrMain Floor King: br-King bedbr-Private entrance to front porchbrbrMain Floor Queen: br-Queen bedbrbrMain Floor Twinbr-Built-in Twin BedbrbrUpstairs Loftbr-3 Twin bedsbrbr-Full Hall Bath with stand-up Shower and clawfoot TubbrbrHIGHLIGHTS:br-Outdoor waterfront furnished terrace and deck - access to decks or porch from main entriesbr-Small fishing and boat launch pier on the pondbr-Kayaksbr-Mulitple living spaces: family room, living room and loftbr-BBQ Gas grill (propane tank provided)br-Dining room table with seating for 8br-Breakfast bar with seating for 3br-Vermont casting gas stovebr-High Speed Internet and WiFi br-Flatscreen TV'sbr-Luxury Westin Heavenly mattress in milk house, fine linens, complimentary toiletries Starter Kit, and boutique-level servicebr-Parking for multiple cars in drivewaybr-Full-size washers/dryers located on the main floorbr-Non-Smoking brbrProperty Distance to: br-Downtown Annapolis – 4 miles br-U.S. Naval Academy – 4 miles br-Washington, DC – 33 miles br-Baltimore - 33 milesbr-Great Frogs Winery - .4 milesbr-Quiet Waters Park - 4.2 miles by land - closer by sea!br***************br* Welcome Gift Basketbr* Amenity & Supplies pack, a starter set of soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.br* All beds are made for you with freshly-laundered sheets & towels.brbrHouse RulesbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the house at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Be respectful of the house and contents - it is someone's home and the owners live in the home when not renting it. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Read More

    5 Bed
    2 Baths
    Sleeps 10
    $582 / Nightly
  • Property-10 Image 1
    (13)
    Private Vacation Home
    Great location, free parking
    Annapolis, Maryland, United States

    Near Everything! Walk to Historic Annapolis & USNA! Even better--take the Water Taxi! brPeaceful oasis in a quiet neighborhood. brHappy modern home. Open floor plan is an entertainer's delight! brHigh ceilings with fans, hardwood floors, kitchen with new appliances. Bedrooms with stocked mini-fridges & coffee makers. All beds have new Serta Cooling Gel mattresses. Home office. Access to spacious one acre front yard. Fenced back yard. Large deck with grill and umbrella.brI want everyone who stays in my home to have the most memorable and enjoyable stay possible! While you’re here, my house is your house.brThe bedrooms sleep up to 8 (2 in each of 4 beds, and 2 on twin mattresses, 2 on queen air mattress in master bedroom), plus 2 more on the living room hide-a-bed sofa. Total: 14brThe basement/garage are not part of the listing. I am usually gone, but may access the basement apartment during reservations. Guests share a path on the side of the property to the rear basement door should I need to access the basement. NO inside spaces are shared.brContact information will be provided after booking.brFREE Ample Off-Street Parking with security light. brTake the Water Taxi to the Historic District! It's just a short walk down the street!brGuests have access to the full house, but for the garage and basement. brOwner may stop by the basement apartment, which is locked with separate egress. Owner keeps a low profile if present.brQuiet, spacious home with new accommodations. brPerfect for 2 couples with kids, a family reunion, or a party of friends or relatives (with owner approval)!brFREE Ample Off-Street Parking with security light. brTake the Water Taxi to the Historic District! It's just a short walk down the street!brUber and Lyft are available. Read More

    4 Bed
    4 Baths
    Sleeps 14
    $284 / Nightly
  • Property-11 Image 1
    Wonderful
    (14)
    Private Vacation Home
    Eastport Gem - Popular house walk to Downtown & USNA
    Annapolis, Maryland, United States

    *Flexible Commissioning Week Cancellation Policy*brbrThis unique 3 Bedroom/3 Bath home is located in Eastport - next door to Bakers and Co. bakery and coffee shop - in a self-contained rear section of our single family home. After parking in the 2-private off-street spaces, walk through the large private backyard with lounge chairs, a dining table for 6, and an outdoor fireplace. Enjoy the complimentary bottle of wine around the outdoor fireplace upon your arrival.brbrThe main door opens into the restaurant-style open kitchen with all high-end appliances, dining and family rooms. Head downstairs to the gaming den with flatscreen TVs, an air hockey table, foosball table, bar, a living room with a pullout sofa and a full bath. Upstairs on the 3rd floor are 3 bedrooms and 2 more full baths. The King bedroom with an en-suite bath opens out to the balcony overlooking the backyard. The balcony goes across the back of the home connecting to the Queen Bedroom. The Queen and Full bedroom share a full bath in the hall. brbrA 10-minute walk to the 6th Street drawbridge and to downtown historic Annapolis. Walk to boat show, Naval Academy, shopping, dining - all Annapolis has to offer.brbr**COVID - 19 Extra Special Precautions: Our guests' and staff's health is our top priority. Our cleaners are taking every precaution when cleaning this home and making sure it meets CDC standards. We are going above and beyond to ensure all surfaces and touch points are being cleaned thoroughly and disinfected (including all light switches, faucets, doorknobs, cabinet handles, remotes, etc.). You will have self check-in and no physical interaction with anyone.**brbrBe sure to ask about discounted rates for extended stays.brbrSLEEPING ARRANGEMENTS 3 BR / 3 BA / Sleeps 8: brKing Suite: br-Second Floor br-King Bed br-Full en-suite bathbrbrQueen guest room: br-Second Floorbr-Queen bed br-Full bath in the HallbrbrDouble guest room br-Second Floorbr-Full bed br-Full bath in the HallbrbrLower Level Denbr-Full sleeper-sofa (only comfortable for one)br-Floor Mattressbr-Full bathbrbrHIGHLIGHTS:br-Gorgeous, gourmet kitchen with high-end appliances, a pizza oven, bar-grade ice maker, 6-burner stove and 2 dishwashers!br-Lower level multi-room gaming denbr-Dining room table seats 6br-Kitchen bar seats 4br-Large outdoor lounging and dining spacebr-Outdoor fireplace with supplied firewoodbr-Gas Grillbr-Balcony off back stretching across both the King and Queen bedroomsbr-Private Driveway with room for 2 cars; additional non-restricted street parking.br-High Speed Internet (1 gig fios internet) and WiFi br-Flat Screen TVbr-Luxury bed and bath linens, complimentary toiletriesbr-Starter Kit, and boutique-level service br-Full-sized washer & dryerbr-Coffee maker with starter kit of coffees and creamersbr-Non-Smoking br-Dogs allowed with $150 non-refundable pet fee per pet paid prior to check-in.br-Keyless entry. Drive straight to your rental home and enter the back door with an electronic lock code. Prior to your visit, we will send you our mobile app with directions and full instructions.brbr***************brProperty Distance to: br-Downtown Annapolis – .6 miles (3 mins)br-U.S. Naval Academy – .9 mile (5 mins)br-Washington, DC – 32 miles br-Baltimore - 30 milesbr***************br* Welcome gift with wine and snacks.br* Amenity & Supplies pack, a starter set of soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.br* All beds are ready made for you with freshly-laundered sheets & towels in the baths.brbrHouse RulesbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.brCheck-in time: 4:00 pmbrCheck-out time: 11:00 am Read More

    3 Bed
    3 Baths
    Sleeps 8
    $449 / Nightly
  • Property-12 Image 1
    Exceptional
    (20)
    Apartment
    Bay View Studio Apartment
    Annapolis, Maryland, United States

    Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private patio, and hot tub! 50 ft of waterfront make this private walk-out garden-level apartment nestled in a small wooded oasis near downtown Annapolis a gem. Walk to the marinas or the Sailing School to catch a water taxi to downtown or book a private sail or fishing tour. Walk to Port Annapolis to get some fresh baked goods at Black Market Bakery. brbrAccess the large 1000+ sf private apartment from a rear separate entrance of this owner-occupied home. There is dedicated space for 2 cars at the end of the driveway. brbrThe King bed is spacious. The Queen sleeper sofa by American Leather is the most comfortable on the market. Note that this apartment is a studio, and the bedroom is open to the living space and queen sleeper sofa. brbrEnjoy high speed internet during your stay. Watch your shows on the flat screen TV using your streaming accounts (there is no cable; bring your passwords to log in to your favorite steaming channels such as Netflix, AppleTV, Amazon Prime, YouTube, etc.). There is an XBOX and a large collection of DVDs for some old-school movie thrills.brbrIMPORTANT NOTE REGARDING TAXES: This lodging is listed on multiple platforms. While VRBO does automatically collect the Maryland 6% Lodging Tax, it does not collect the City of Annapolis Lodging Tax which is 8% of your booking fee as of July, 2023. For VRBO guests only, your host will collect this tax from you during your stay and submit to the City of Annapolis.brbrIMPORTANT NOTE REGARDING INSURANCE: When you book with VRBO, you should see an option for either paying an insurance fee (flat rate ~$59) or submitting a refundable deposit. Choose whichever option best suits you. These transactions are with VRBO, not the host. br Read More

    1 Bed
    1 Baths
    Sleeps 4
    $211 / Nightly
  • Property-13 Image 1
    (22)
    Private Vacation Home
    Hanover House across from USNA Gate 3!
    Annapolis, Maryland, United States

    The owners (two USNA grads) fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a quiet street next to the Naval Academy and St. John’s College, it’s a 5-minute walk to City Dock/Main Street. Perfect for Navy parents, Alumni, weddings, sailors, weekenders, sightseers, Legislators and Work-cationers.brbrFully renovated in 2017, the kitchen is equipped with high-end stainless steel appliances (including a dual-temperature wine fridge!), granite countertops and opens up to the dining and living areas. The original hardwood floors have been re-finished, adding to the historic Annapolis charm and feel. In addition to the comfortable sleeping arrangements for 8, step out back into a massive outdoor living and dining deck with a gas grill and a fire pit. Head upstairs to the 4 bedrooms and 2 baths and relax on the private King Suite balcony.brbrFor guests with cars, there are many safe, easy public parking options (some free) available within walking distance. brbr**COVID - 19 Extra Special Precautions: Our guests and staff's health is our top priority. Our cleaners are taking every precaution when cleaning this home and making sure it meets CDC standards. We are going above and beyond to ensure all surfaces and touch points are being cleaned thoroughly and disinfected (including all light switches, faucets, doorknobs, cabinet handles, remotes, etc.). You will have self check-in and no physical interaction with anyone. brbrBe sure to ask about discounted rates for extended stays.brbrSLEEPING ARRANGEMENTS 4 BR / 2.5 BA / Sleeps 8: brKing Suite: br- 2nd Floorbr- King Bed br- Oversized shower walk-in shower with rain shower head and double vanitybr- California Closetsbr- Private BalconybrbrSunny Front Guest Room:br- 2nd Floorbr- Queen Bed br- Jack-n-Jill Full Bath with Tub and ShowerbrbrTwin Guest Bedroom: br-Second Floorbr-Two twin bedsbr- Jack-n-Jill Full Bath with Tub and Showerbrbr3rd Floor Bedroom/Office Combo: br- Queen Bedbr- Office Desk and Chairbr- Additional A/C unitbr- Flatscreen Smart TVbrbrHIGHLIGHTS:br- Spacious gourmet kitchenbr- Eat-in kitchen counter seats 2br- Dining room table seats 6br- Spacious outdoor living, dining and fire pit areabr- WiFi br- Big Screen Smart TV'sbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service br- Washer & dryer located inside the homebr- Non-Smoking br- No petsbr- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations.br- Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Prior to your visit, we will send you our mobile app with directions and full instructions.br***************brProperty Distance to: br- U.S. Naval Academy – Across the Street from Gate 3 br- Washington, DC – 30 miles br- Baltimore - 25 milesbrbr***************br* Guest Welcome Basket!br* Amenity & Supplies pack, a starter set of soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.br* All beds are ready made for you with freshly-laundered sheets & towels.brbrHouse RulesbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.brCheck-in time: 4:00 pmbrCheck-out time: 11:00 am Read More

    4 Bed
    3 Baths
    Sleeps 8
    $350 / Nightly
  • Property-14 Image 1
    Exceptional
    (1)
    Private Vacation Home
    The Fleet's Inn just steps from the Waterfront in this modern Historic home
    Annapolis, Maryland, United States

    Stay just steps from the Annapolis waterfront! Cherished by the multi-generational Navy owners who have updated the modern home, while maintaining the charm of residing on the Historic District's Fleet Street. Enter the sunny family room decorated in full Semper Fi pageantry. Head back to the gourmet kitchen, with sleek granite counter tops, stainless steel appliances and all of the kitchen tools you'll need for your stay. Head out to the private fenced stone patio where you'll find a BBQ grill and seating for 4 under the umbrella at the table. In the hall of the main floor you'll find the powder room and full laundry room.brbrHead up the Navy-decorated stairway to the 2 bedrooms and 2 full baths on the second floor. The en-suite primary Bedroom has a Queen bed, flatscreen TV and a shower/tub combo. Across the hall is the guest bedroom with 2 twin beds and an en-suite full bath with stand-up shower.brbrWhen you are ready to see the sights of Annapolis, step outside on to the cobblestone street just one block to the City Dock, shops, restaurants and the Naval Academy. brbr**COVID - 19 Extra Special Precautions: Our guests' and staff's health is our top priority. Our cleaners are taking every precaution when cleaning this home and making sure it meets CDC standards. We are going above and beyond to ensure all surfaces and touch points are being cleaned thoroughly and disinfected (including all light switches, faucets, doorknobs, cabinet handles, remotes, etc.). You will have self check-in and no physical interaction with anyone. brbrBe sure to ask about discounted rates for extended stays.brbrSLEEPING ARRANGEMENTS 2 BR / 2.5 BA / Sleeps 4 (plus 1 more on an air mattress - available upon request): brPrimary Bedroom: br- Second Floorbr- Queen Bed br- Flatscreen TVbr- En-Suite full bathbrbrTwin Guest room: br- Second Floorbr- Two Twin Beds br- Flatscreen TVbr- Full en-suite bathbrbrHIGHLIGHTS:br- Full gourmet kitchen with stainless steel appliances and granite countertopsbr- Private back brick patio with outdoor dining table for 4br- Eat-in kitchen table seats 2br- Seating for 4 at the folding table that pops up in the living br- BBQ Grill with a tankbr- WiFi br- Multiple flatscreen TV'sbr- Luxury linens, complimentary toiletries Starter Kit, and boutique-level service br- Washer & dryer located inside the homebr- Non-Smoking br- No petsbr- Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations.br- Keyless entry. Drive straight to your rental home and enter the electronic lock code on the front door. Prior to your visit, we will send you our mobile app with directions and full instructions.br***************brProperty Distance to: br- U.S. Naval Academy – 1 blockbr- Washington, DC – 30 miles br- Baltimore - 25 milesbrbr***************br* Guest Gift Basket with wine, snacks, coffee pods and creamers!br* Amenity & Supplies pack, a starter set of soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.br* All beds are ready made for you with freshly laundered sheets & towels.brbrHouse RulesbrReservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking/no pets. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind.brCheck-in time: 4:00 pmbrCheck-out time: 11:00 am Read More

    2 Bed
    3 Baths
    Sleeps 4
    $379 / Nightly
  • Property-15 Image 1
    Exceptional
    (3)
    Private Vacation Home
    Beautiful waterfront home awaits you in Eastport
    Annapolis, Maryland, United States

    STR22-145133 The Cottage on Back Creek has it all. Located less than a mile from downtownbrAnnapolis and the Naval Academy, this Eastport home offers spectacular viewsbrof Back Creek and the Chesapeake Bay. You can walk to many locally-ownedbrrestaurants, all within half a mile of the cottage. Whether you like to eatbrbreakfast out, are looking for a fun pub lunch, or want to treat yourselves to finebrdining, it is all right here. Enjoy an easy walk across the Spa Creek Bridge tobrdowntown Annapolis or take a water taxi ride from the cottage dock.brThis four-bedroom home offers a gourmet kitchen with high-end appliances,brmultiple comfortable gathering and eating areas, sleeping for nine, a second floorbrbalcony to enjoy your morning coffee while overlooking the water, and a dock tobrsit on to watch the wildlife and boats go by. The large deck is a great place tobreat outside or relax with a good book.brThe Cottage on Back Creek is the perfect place to enjoy the best of Annapolisbrwithout the hassles of downtown parking. Read More

    4 Bed
    4 Baths
    Sleeps 9
    $983 / Nightly
  • Property-16 Image 1
    Exceptional
    (2)
    Private Vacation Home
    Huge deck overlooking water
    Annapolis, Maryland, United States

    Renovated, charming Annapolis home on half-acre lot fronting Burley Creek. Just a short paddle to Whitehall Bay and expansive waters of the Chesapeake Bay. Four sliding glass doors overlook the water with panoramic views of evening sunsets. Home features 5 bedrooms, 4.5 bathrooms, newly renovated kitchen, huge deck overlooking the water, outdoor grill, kayaks, SUPs. Historic downtown Annapolis harbor only 15 minutes by car OR boat. Dock accommodates 40-foot boat. MLW six feet.brWaterfront with pier and sunset views. Large deck with ample seating and large dining table.brGuests will enjoy the entire two-level house situated on one-half acre on the water. Water access via the dock with paddle board and kayak available for your enjoyment.brOther things to notebrThere is a sailboat and power boat moored at the dock. During your stay someone may access the sailboat on the dock. We promise any disruption will be minimal.brbrDue to COVID 19 we ask guest to be responsible and keep risks to a minimum. We ask you follow all local, state and federal health guidelines to protect yourself, others and to prevent the spread of COVID 19. Gathering should be limited to 10 or less people. Wash hands frequently and wear a mask when social distancing is not possible. If you exhibit any signs or symptoms of Covid 19, please contact your doctor immediately for advice and instructions.brbrAt this time no parties or events are allowed at the house.brbrParties/events held at the house will need written preapproval via the Airbnb app. A party fee (depending on the scope of the event) and a "party deposit" fee may be applicable. Also, the cleaning fee may be adjusted based on the scope of the event.brPlease contact the host for more information, pricing and preapproval for your specific event.brLicense numberbr140873 Read More

    5 Bed
    5 Baths
    Sleeps 12
    $794 / Nightly
  • Property-17 Image 1
    Exceptional
    (1)
    Apartment
    Private Annapolis Guest Apartment! Walkable to downtown! Location!
    Annapolis, Maryland, United States

    Keep it simple at this peaceful and centrally located guesthouse. This charming guest house w/ private access is located right in the heart of Murray Hill, Annapolis. Walkable to the Navy Stadium, West Street restaurants & bars and Downtown Annapolis. brbrbrThis in-law apartment/ guest house is completely private and has its own entrance. brbrFully furnished with the following amenities: fridge / freezer, Kuerig machine, large work/ desk area, cable tv, wireless internet, large shower, 1 bed (queen size with trundle storage), several windows, great lighting. brbrFree street parking is available. Has everything you need for a short or long term stay!brbrbrDoor has a smart lock. Code will be provided 24 hrs before checkinbrbrTo open: Get code from the host. Enter the code and turn the knob to the right. The “Schlage” button will flash green. Then use the bottom handle to open the door. brbrTo lock door from outside: press the “Schlage” button and turn the knob to the left. brbrNo smoking and no pets pleasebrbrThe pool, grill and patio area are not available for use Read More

    1 Bed
    1 Baths
    Sleeps 3
    $275 / Nightly
  • Property-18 Image 1
    Private Vacation Home
    Your Annapolis adventure starts here!!
    Annapolis, Maryland, United States

    Over 1500 sq ft of light filled living space offering 3 bedrooms and 2.5 bathrooms. Take the Water-Taxi to the Naval Academy, Annapolis Waterfront Restaurants, Eastport, Art & Historic Districts. The open floor plan with calming color palettes and abundance of br windows create an open, airy, relaxing atmosphere! Richly furnished with oversized leather sofa, overstuffed pillows, comfy throws make it a perfect place to decompress after all your Annapolis Adventures. . There's multiple areas with plenty of room for family and friends to stretch out, relax and binge watch your favorite shows! br Feeling inspired to COOK? The open concept kitchen has everything you need for cooking those special meals along with an outside gas grill. If Carry-Out is what you crave, there is no shortage of great eats in Annapolis. The adjoining family room is a perfect spot for relaxing, entertaining, daily dinning, coffee and conversations. br Unwind outdoors on private fenced patio with firepit and outdoor seating, made magical with bistro lights hung from overhead trees, bubbling fountain and cocktail table, which is perfect for dinning ALFRESCO. br Upstairs are the 3 very comfortable bedrooms with ceiling fans & 2 full bathrooms. The owner's suite offers a luxurious king size bed, private bathroom, smart TV, private walk-in closet with luggage rack. The well-appointed hall bath is convenient to the other 2 bedrooms which offer beautiful luxurious queen size beds. brbr Walking distance to marinas, parks, shopping, restaurants and water taxi. Less than 7 min drive to Must-See Annapolis Attractions.brbrCome and Stay Awhile and Enjoy the Space, Privacy and Relaxation you Crave and adventures you deserve!! Read More

    3 Bed
    3 Baths
    Sleeps 6
    $285 / Nightly
  • Property-19 Image 1
    Exceptional
    (1)
    Private Vacation Home
    Charming 235-yo former tavern 1 block to water/shops
    Annapolis, Maryland, United States

    235 yo home, formerly a tavern & inn where Thomas Jefferson bought salt & stockings. Beautifully furnished with antiques and modern pieces. Great private back garden patio with fence/trees. Original wood floors. Quiet street one block off of Main St. 5 min walk to sunrises/sunsets at City Dock + tons of restaurants, pubs, & shops on Main St, West St, MD Ave & Eastport. Steps from Naval Academy & St. Johns College. 10 min drive from Quiet Waters Park & more. Friendly neighbors. Walkable to ghost tours, historic tours, etc. Looking for good stewards of this historic gem. (Boat show weekends will have challenging parking. There is free parking at garage at end of St John's St but will fill quickly) Read More

    3 Bed
    2 Baths
    Sleeps 5
    $700 / Nightly
  • Property-20 Image 1
    (24)
    Private Vacation Home
    Charm & Style in this Renovated Eastport Home
    Annapolis, Maryland, United States

    This fully renovated three bedroom home sleeps 8. A touch of Key West comes to Eastport in this beautiful cottage style home. Beautiful open concept kitchen, dining and family room. Off street parking holds 3-4 cars. Read More

    3 Bed
    2 Baths
    Sleeps 8
    $466 / Nightly
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Annapolis Tourist guide :

What are the most popular tourist destination in a Annapolis ?

Annapolis, Maryland is an iconic tourist destination known for its rich history, breathtaking waterfront, and vibrant cultural scene. From its historic district to its stunning parks and natural attractions, it is easy to see why many travelers flock to this charming city.

To start, the historic district is a must-see for any tourist visiting Annapolis. The district is full of colonial-era buildings, charming brick sidewalks, and quaint alleys that add to the city's charm. American history buffs will appreciate seeing the Maryland State House, the oldest in the country still in use, as well as the U.S. Naval Academy, a key site of American military history.

Another popular spot for tourists is City Dock, which is located right in the heart of downtown Annapolis. The dock is a lively hub of activity, where sailing boats and luxury yachts come and go, and where visitors can enjoy outdoor dining while taking in the stunning views of the Chesapeake Bay.

For outdoor enthusiasts, Quiet Waters Park is a perfect spot to explore. The park has more than 300 acres of bucolic land, picnic areas, and recreational amenities. Visitors can enjoy hiking, biking, kayaking, or even fishing. The park also hosts numerous cultural events throughout the year, including concerts, festivals, and art shows.

Finally, the Chesapeake Bay Maritime Museum is a popular attraction for visitors of all ages. This museum offers exhibits on the region's maritime history, boatbuilding, ecology, and much more. Additionally, visitors can take a tour of the lighthouse, explore the historic shipyard, or even take a sail on a historic skipjack.

In conclusion, Annapolis, Maryland is a unique destination that has something to offer every traveler. From the historic district and the City Dock to the natural beauty of Quiet Waters Park and the Chesapeake Bay Maritime Museum, there are endless ways to explore this charming city. Whether you’re here for a weekend getaway or a longer vacation, Annapolis is sure to be an unforgettable experience.

What is the average price per night in Annapolis ?

If you're planning a trip to Annapolis, Maryland, you may be wondering how much you can expect to pay for a vacation rental. The average price per night for a vacation rental in Annapolis typically ranges from $150 to $250, depending on the size, location, and amenities of the rental.

Factors that can affect the price of a vacation rental in Annapolis include the number of bedrooms, the location of the rental (such as whether it's on the water or in the historic district), and the time of year you're planning to visit.

If you're looking to save money on your vacation rental, consider traveling during the off-season (late fall, winter, and early spring) when prices may be lower. Additionally, booking early or last-minute can sometimes result in lower prices.

Overall, Annapolis offers a range of vacation rentals at varying price points, making it possible to find something suitable for any budget.

When is the best time to holiday in Annapolis ?

Annapolis, Maryland is a charming and historic city tucked into the Chesapeake Bay region. This unique location and the city's rich history means there are great times to visit all year round - each with its own unique perks and events.

Summer is undoubtedly a popular time to visit Annapolis. With warm temperatures, a bustling harbor, and outdoor dining on the waterfront, it's easy to see why visitors flock to the city during this season. From sailing and kayaking on the bay to attending the popular Eastport Pirate Festival or watching Wednesday night sailboat races, there is always something exciting happening in the summer.

Fall is a beautiful time to visit Annapolis, with the colorful foliage in the nearby state parks and cooler temperatures - perfect weather for walking around the historic downtown. The Annapolis Boat Show, one of the largest in-water boat shows in the United States, is also in the fall, drawing thousands of visitors each year.

Winter sees fewer visitors to Annapolis, but that doesn't mean there's less to do. The city's historic homes and museums are decorated in festive holiday cheer, and the city's annual lighting of the city tree is a beloved tradition. Ice skating at the popular Quiet Waters Park and shopping for unique gifts at the Christmas markets are just a few of the wintertime activities visitors can enjoy.

Spring is a gorgeous time to visit Annapolis and witness the city waking up from its winter slumber. The cherry blossoms are in full bloom and outdoor activities such as hiking, biking, and bird watching are popular. Additionally, the annual Annapolis Spring Sailboat Show draws crowds to the city's harbor for an exciting weekend full of boats and adventure.

In conclusion, Annapolis, Maryland is a city that can be visited all year-round, as each season offers its unique charm and events. Whether it's sailing on the bay in the summer or exploring the historic downtown in the fall, there's something for everyone in Annapolis.

What are the most popular things to do in Annapolis ?

For travelers seeking a unique vacation spot, Annapolis, Maryland, offers a wealth of activities to explore. Known for its rich history, cultural attractions, and stunning waterfront location, the city has something for everyone.

One of the most popular things to do in Annapolis is to explore the city's historic district. This area is home to a wealth of well-preserved 18th-century architecture, charming boutiques, and excellent restaurants. Visitors can take a guided walking tour with a knowledgeable local guide or explore on their own.

Another must-see attraction in Annapolis is the United States Naval Academy. This renowned university and military institution is one of the city's most iconic landmarks. Visitors can tour the beautiful grounds, check out the impressive museum, and watch midshipmen perform their daily drills.

For those seeking outdoor recreation, Annapolis offers plenty of options. Visitors can rent a boat or kayak to explore the Chesapeake Bay, or take a relaxing cruise on one of the city's many water taxis. Additionally, the city's many parks and nature trails offer opportunities for hiking, biking, and wildlife watching.

Foodies will find plenty to savor in Annapolis. The city is famous for its seafood, and visitors can dine on fresh crabs, oysters, and other local favorites at one of the many excellent seafood restaurants. Additionally, the city's thriving arts scene means that there are plenty of cultural events to enjoy, from music to theater to festivals.

No matter what your interests, Annapolis offers a wealth of activities and attractions for travelers of all ages. From exploring the city's history and culture to discovering its natural beauty and dining scene, there's something for everyone in this beautiful city. So why not pack your bags and head to Annapolis for your next vacation? You won't be disappointed!

Most popular vacation rentals in Annapolis

  • thumb
    $ 317.00 avg/night
    4
    • 4 Beds
    • 3 Baths
    • 16 Guest(s)
    ?Your Annapolis Retreat near the beach and downtown? Annapolis, Maryland, United States

    Welcome to our recently renovated retreat in Annapolis. The place is located minutes from... Read More

  • thumb
    $ 165.00 avg/night
    10
    • 3 Beds
    • 3 Baths
    • 10 Guest(s)
    Freshly renovated 3-story home 1 block from USNA! Annapolis, Maryland, United States

    Summary:Welcome to The Wardroom!Originally built in 1902 and completely renovated in 2014, this 3... Read More

  • thumb
    $ 500.00 avg/night
    2
    • 0 Beds
    • 1 Baths
    • 4 Guest(s)
    Downtown furnished apartment - walking distance to restaurants Annapolis, Maryland, United States

    Church owned 2nd Floor apartment in historic house - fully furnished - eat-in kitchen, dining... Read More

  • thumb
    $ 237.00 avg/night
    10
    • 1 Beds
    • 1 Baths
    • 2 Guest(s)
    Charming Annapolis Guest House Annapolis, Maryland, United States

    This charming guest house with private access is in a great location! Just 2 miles from the Naval... Read More

  • thumb
    $ 338.00 avg/night
    3
    • 3 Beds
    • 3 Baths
    • 9 Guest(s)
    History & Charm Near the Annapolis City Dock Annapolis, Maryland, United States

    Previously-managed home with multiple 5 Star reviews, now under new management. This charming... Read More

  • thumb
    $ 211.00 avg/night
    20
    • 1 Beds
    • 1 Baths
    • 4 Guest(s)
    Bay View Studio Apartment Annapolis, Maryland, United States

    Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows... Read More

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    $ 275.00 avg/night
    1
    • 1 Beds
    • 1 Baths
    • 3 Guest(s)
    Private Annapolis Guest Apartment! Walkable to downtown! Location! Annapolis, Maryland, United States

    Keep it simple at this peaceful and centrally located guesthouse. This charming guest house w/... Read More

  • thumb
    $ 182.00 avg/night
    5
    • 5 Beds
    • 4 Baths
    • 15 Guest(s)
    3 Story Stunner in Murray Hill <1 mile from USNA! Annapolis, Maryland, United States

    Summary:This is an *amazing* 3 story / 5 bedroom house with a finished basement! This is the... Read More

  • thumb
    $ 508.00 avg/night
    16
    • 3 Beds
    • 3 Baths
    • 10 Guest(s)
    ***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere. Annapolis, Maryland, United States

    1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking!... Read More

  • thumb
    $ 486.00 avg/night
    4
    • 4 Beds
    • 2 Baths
    • 10 Guest(s)
    Escape Villa in Downtown Annapolis Annapolis, Maryland, United States

    Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial... Read More

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