Vacation Rentals By Owner In Annapolis, MD

$383.04

Annapolis Charm –Bright 3BR in Downtown

Annapolis, Maryland, United States

Welcome to this spacious and fully furnished home, designed to be your comfortable home away from home. Spanning three levels, the layout offers the perfect balance of together time on the main floor and private time in the finished basement.brbrWhether you are here for a family vacation or a remote-work trip, you’ll find plenty of space to relax and recharge.brbrTop Features at a GlancebrPremium Sleep: Super comfortable beds with crisp cotton sheets.brbrEntertainment Hub: Finished basement with a 65” Smart TV.brbrRemote-Work Ready: Dedicated desk with lamp & comfortable chair.brbrRoom for Everyone: 3 levels of living space to spread out.brbrChef’s Kitchen: Fully equipped with dishwasher, blender, and coffee maker.brbrThe LayoutbrUpstairs: Rest & Recharge (3 Bedrooms) We know a good night's sleep is the most important part of your stay. That's why we prioritize super comfortable beds, topped with soft, high-quality cotton sheets, plush pillows, and extra warm blankets.brbrBedroom 1: Queen BedbrbrBedroom 2: Queen BedbrbrBedroom 3: Bunk Bed (Perfect for 2 kids or young adults)brbrFull Bathroom: Features a tub/shower combo, fresh towels, and a toilet with a bidet for added comfort.brbrMain Floor: Gather & Dine The heart of the home! Since there are no bedrooms or baths on this level, it is 100% dedicated to quality time.brbrLiving Room: A cozy space to play board games, watch TV, or relax while dinner simmers.brbrKitchen: A spacious, functional design equipped with a stove, oven, microwave, fridge, and dishwasher. We provide all the pots, pans, and kitchenware you need—plus a blender, water kettle, and coffee maker for your morning routine.brbrCleaning Essentials: We’ve stocked the pantry with Windex, Clorox, dish soap, and laundry detergent for your convenience.brbrDownstairs: Work & Play (Finished Basement) The ultimate bonus space! Perfect for sending the kids to play or getting some work done in peace.brbrSleeping: Full-size foldout sleeper couch (Sleeps 2).brbrEntertainment: Massive 65” TV for movie nights.brbrWorkspace: A dedicated desk with a lamp, ottoman, and comfy chair.brbrConvenience: Easy access to the downstairs bathroom.

3

Bed

2

Bath

8

Sleeps

$519.12

/ Nightly

Private Vacation Home

Historic Annapolis Renovated Rowhouse (c.1885) One Block to City Dock & the U.S. Naval Academy

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrGreen on Fleet – Historic Annapolis Rowhouse (c.1885) One Block to City Dock & the U.S. Naval Academy brbr brbrStay in this beautifully renovated historic home in the heart of downtown Annapolis, just one block from City Dock, the U.S. Naval Academy, the State House, shops, and restaurants. Step outside onto a charming cobblestone street and experience the city’s historic district at its best. brbr brbrBuilt between 1885–1887, this classic Annapolis worker’s rowhouse has been part of the Fleet Street neighborhood for more than 130 years. Originally rented to working families connected to the city’s busy waterfront, homes like this formed the heart of Annapolis’ historic maritime community. Around 1910, the house was home to a Chesapeake Bay oysterer, whose story inspired the artwork above the bar. brbrToday, Green on Fleet blends historic character with modern comfort—offering guests a cozy retreat with curated interiors and a private brick patio just steps from the waterfront. brbr brbrPlease Note: No on-site parking is provided. brbr brbrSleeping Arrangements (Sleeps 4 | 2BR / 1.5BA) brbr brbrPrimary Bedroom (2nd Floor) brbr• California King bed brbr• Hall full bath brbr brbrGuest Bedroom (2nd Floor) brbr• Queen bed brbr• Hall full bath brbr brbrHighlights brbr• Gourmet kitchen with stainless appliances & granite countertops brbr• Private brick patio with seating & BBQ grill brbr• Dining table for 6 + convertible bar brbr• WiFi & Smart TV in family room brbr• Washer & dryer brbr• Keyless entry brbr• Luxury linens & starter supply kit included brbr brbrDistance to: brbr• U.S. Naval Academy – 1 block brbr• Washington, DC – 30 miles brbr• Baltimore – 25 miles brbr brbrHouse Rules brbr• Primary renter must be 25+ and present during stay brbr• No parties, pets, events, or smoking brbr• Respect neighbors and quiet hours brbr• Check-in: 4 PM | Check-out: 11 AM

2

Bed

1

Bath

4

Sleeps

$450.3

/ Nightly

Cottage

Walk to everything! Downtown Historic Annapolis “Arts District”

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Bed

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Sleeps

$430.03

/ Nightly

Private Vacation Home

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Annapolis, Maryland, United States

Incredible location in the Historic District of Annapolis. Walking distance to the Naval Academy, St. Johns College, and Annapolis waterfront. This 100+ year old charming row house offers a scenic front porch and beautiful backyard English garden w/brick patio where you enjoy the sounds of the extraordinary USNA Chapel. The home has 3 bedrooms upstairs, 1 full/1 half baths, living room, separate dining room, and kitchen. brbrThis home is open year round with a two night minimum stay.brbr RENT FOR COMMISSIONING WEEK, WEDDINGS, AND ALUMNI REUNIONS, OR A FAMILY VACATION:brbrThis home is conveniently located for any Annapolis events; and will surely make for a memorable stay in Maryland’s capital city. br

Bed

Bath

Sleeps

$663.45

/ Nightly

Private Vacation Home

Eastport Haven House

Annapolis, Maryland, United States

Welcome to our custom Craftsman in the exclusive Maritime Eastport section of Annapolis. Surrounded by the city's best restaurants (Ruth's Chris, ChartHouse, Vin 909 and many, many others) as well as home to some very famous neighbors it's one of the most desirable locations in town. A short stroll across a quaint drawbridge and your downtown for shopping and USNA. Very spacious home with 4 bedrooms 4 baths, parking for 4 cars and a pool table. Truly a million plus dollar property!brbrCustom built in 2014 it's one of a kind and spotless. Ideal for two families with 4 full bathrooms and two living areas and a large walkout basement with a pool table . First floor master suite , 3 bedrooms upstairs with a pull out in threefold living room area. Pool table , sofas and full bathroom in walk out basement . Fantastic water views of AYC , USNA , Spa Creek and downtown. We back up to the brand new exclusive South Annapolis Yacht Center where all the mega yachts dock.brbrThe back area leads to a the exclusive South Annapolis Yacht Center that is getting renovated and rebuilt as of March 2019. Construction is finished behind us and further down the peninsula . Great Spa creek water views of The Bridge downtown AYC and USNAbrbrMessage first about pets - no instant booking . Extra pet fee required . We have a service animal in our family and are not required to accept . Please Inquire first . No parties - Bach / Ette included . No confetti / taping on walls . Noise complaints will end reservation .

Bed

Bath

Sleeps

$1378.87

/ Nightly

Private Vacation Home

Historic Downtown Luxury • USNA • Waterfront

Annapolis, Maryland, United States

Welcome to Fair Winds DTA (Downtown Annapolis): a beautiful, spacious, and sunlit historic home on gorgeous Prince George Street in the heart of downtown Annapolis. Less than a minute walk from both the vibrant waterfront and the Naval Academy’s Gate 1, this home’s location quite simply cannot be beat. It’s perfect for Naval Academy families and Annapolis visitors alike!brbrBlending coastal elegance with warm hospitality — we invite you to unwind and enjoy an authentic Annapolis stay.brbrAnnapolis License: RENT-002655-2025brbrThis beautifully restored historic home sits right in the heart of downtown Annapolis and waterfront bustle. Featuring five spacious bedrooms and 3.5 baths, it blends timeless charm with modern luxury. Every room is thoughtfully appointed with high-end finishes and authentic architectural details. Enjoy morning coffee or evening cocktails on the oversized patio overlooking the town — the perfect balance of history, elegance, and coastal serenity.

5

Bed

3

Bath

10

Sleeps

$1138.41

/ Nightly

Private Vacation Home

Newly-Remodeled Stunning Waterfront Luxury Home w Private Pier in Annapolis, Dog-Friendly

Annapolis, Maryland, United States

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to All Decked Out, your dream escape in the waterfront Oyster Harbor Community of Annapolis, a tranquil retreat on the Annapolis Neck Peninsula. This beautifully renovated 4-bedroom, 3-bath home blends modern elegance with timeless coastal charm. With sweeping water views, a private pier, multiple decks, and seamless Chesapeake Bay access, this home is perfect for boating enthusiasts, families, and anyone craving tranquility by the water. brbr brbrSpacious Coastal Living brbrThe open concept layout is designed for gathering and relaxation. brbrExpansive windows framing serene waterfront views brbrWaterfront dining room with seating for 6 brbr brbrChef’s Kitchen brbrA true entertainer’s kitchen featuring: brbrLarge island with breakfast bar seating for 4 brbrNew stainless steel appliances brbrAmple prep space brbrFully stocked with cookware and dinnerware for 12 guests brbrCoffee bar in the kitchen (plus a second coffee bar in the Dining Room and a third in the King Suite) brbr brbrSleeps 12 brbrMain Level brbrDouble Queen Suite (sleeps 4) with en-suite bath with dual access to Living room brbr brbrSecond Level brbrWaterfront King Suite with luxury bath, sitting room, coffee bar & deck access brbrWaterfront Double Queen Bedroom (sleeps 4) with deck access brbrFull Bedroom brbrFull Hall bath with shower brbr brbrOutdoor Living brbrPrivate dock brbrCovered deck + upper waterfront deck brbrWaterfront patio with built-in grill & outdoor kitchen brbrWater views from multiple rooms brbrBring your boat, kayak, or simply enjoy sunset views from the dock. brbr brbrCommunity Perks brbrGuests enjoy access to Oyster Harbor’s beach, fishing pier, boat ramp, playgrounds, nature trails, and exercise course. brbrDog-Friendly - $150 non-refundable fee per pet (paid prior to check-in). brbr brbrIdeal Location brbr10 minutes to Downtown Annapolis brbr12 minutes to USNA brbrEasy access to DC & Baltimore (33 miles) brbrParking for 2-4 SUVs/cars in the circular driveway (garage parking not included) brbr brbrPerfect for family gatherings, Navy visits, or peaceful waterfront retreats. brbr brbrLocation Highlights: brbrNestled in the quiet Oyster Harbor community, this property is minutes from downtown Annapolis, shopping, dining, and entertainment.

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Bath

Sleeps

$403.99

/ Nightly

Private Vacation Home

Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis, Maryland, United States

SPECIAL OFFER!!! Receive 10% more as discount when you book from N0V 21st - NOV23! brRelax and recharge in our peaceful beachside home—just minutes from downtown Annapolis and top local attractions. Nestled in a quiet wooded enclave within the Cape St. Claire Private Beach Community and near the pristine shores of Sandy Point Beach, this refined escape offers a harmonious blend of upscale comfort with Chesapeake charm. Enjoy easy access to scenic beaches, tranquil nature, and the perfect setting for a restful getaway.brInside, enjoy a bright, open living space with plush seating, smart TV, and large windows. The fully equipped kitchen includes a dishwasher, coffee maker, microwave, and all the essentials for home-cooked meals. The dining area seats 8 comfortably and is perfect for meals or entertaining.brbrThere are three bedrooms including a primary suite with queen bed, walk-in closet, and ensuite bath with soaking tub, plus two additional queen bedrooms and a half bath. Crib available upon request.brStay connected and productive with high-speed Wi-Fi, a dedicated workspace, and full laundry amenities. Pet-friendly for up to 2 well-trained pets, and there’s off-street parking including 2 reserved spaces.brbrOutside, relax on the private deck with wooded views or follow the walking trail to the Little Magothy River. You’re just a 15-minute walk or 4-minute drive to Sandy Point State Park, a public beach ideal for a full day by the water or catching sunrise over the Bay.brbrPlease note: Cape St. Claire’s private beach, known for its quiet shoreline and great crab cakes, is only 8 minutes away but reserved exclusively for residents. While guests won’t have access to this beach, Sandy Point Beach offers a fantastic and accessible alternative just around the corner.brbrNearby Attractions & Essentials:br• Sandy Point State Park – 15 min walk / 4 min drivebr• Downtown Annapolis / U.S. Naval Academy (USNA) – 12–15 min drivebr• Maryland State House & City Dock – 13 minbr• Chesapeake Bay Bridge – 6 min / 1.5 miles from the propertybr• Cape St. Claire Community & Shops – 8 minbr• Bay Hills & USNA Golf Club – short drivebr• Jonas Green & Quiet Waters Parks – nearbybr• Anne Arundel Community College – short drivebr• Anne Arundel Medical Center – short drivebr• Graul’s Market, cafés & restaurants – 7 min drivebr• Conveniently located off Hwy 50 East/West for easy access to the entire region.brbrbrYou will have full access to the entire home during their stay. This includes all three bedrooms, 2.5 bathrooms, the spacious living and dining areas, a fully equipped kitchen, private deck with wooded views, in-unit washer and dryer, and dedicated parking spaces.brbrYou’ll also enjoy easy access to nearby nature trails and a community path that leads to the waterfront. Entry is self-check-in via a secure smart lock—details will be shared prior to your arrival for a smooth and convenient check-in experience.

3

Bed

2

Bath

8

Sleeps

$380.76

/ Nightly

Private Vacation Home

Restful and Charming Home in Eastport

Annapolis, Maryland, United States

We offer a 10% military discount upon request! A cozy home away from home in Eastport located within 1.5 Miles of Historic Downtown Annapolis and 2 miles from US Naval Academy. Conveniently located near numerous restaurants and shopping centers. Plenty of room for indoor and outdoor comfort and activities!brThe spacebrComfortable beds, fully stocked kitchen, and spacious outdoor area with dining table and fire pit! All three bedrooms are located on the second level. Our home offers a king bedroom, queen bedroom, and a full bedroom. We also keep a pack-n-play available for guests to use as needed! Washer and dryer available on site in the basement as well! Note: there is an additional toilet located in the unfinished basement and is not enclosed but still fully functional!brbrGuest accessbrGuests will have access to the entire home during their stay!brbrOther things to notebrWe want to mention we have backyard chickens, but you’ll have no responsibilities to visit or take care of them! They are in a coop/run and stay there!

3

Bed

1

Bath

6

Sleeps

$695.4

/ Nightly

Private Vacation Home

Elegant 3-bedroom house with EV charger in Downtown Annapolis

Annapolis, Maryland, United States

Consider this house your home away from home while you visit Annapolis. This charming retreat features three bedrooms, including two king beds and a cozy twin bed, perfect for families or groups. Guests enjoy a terrific bathroom with a relaxing bathtub and a handy hair dryer. The space stays comfortable year-round with heating and air conditioning. Whether you’re unwinding after a day of exploring or planning your next adventure, this awesome house offers a welcoming spot to recharge. We look forward to hosting you at our place.

3

Bed

1

Bath

6

Sleeps

$1050.43

/ Nightly

Private Vacation Home

GREENNEST is an ENVIRONMENTALLY FRIENDLY Waterfront home close to Annapolis

Annapolis, Maryland, United States

The Timberpeg N. California Douglas Fir Post and Beam construction with Finnish Spruce ceilings is a beautiful stunning design. The open floor plan offers thrilling vistas out onto Martins Cove, a tributary of the Chesapeake Bay. Take advantage of the side screened in porch, front deck on the waterfront and large waterfront screened in porch. Grill and eat outdoors or inside. Enjoy the wildlife and if you are lucky catch a glimpse of a bald eagle soaring across the Cove. You have use of 4 bedrooms and 4 full baths with queen beds in the main house. Basement au pair apartment with full kitchen and full bath.The separate studio above the garage has a double bed and full bath and wet bar and microwave/refrig. The house has non-toxic finishes, sealers and paints. The entire house layout is handicap accessible with main floor accessible with no steps. Grab bars throughout. Kayak, canoe, crab and fish off the dock. Funfor all.

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Bath

Sleeps

$1252.39

/ Nightly

Private Vacation Home

Luxury Waterfront Annapolis home with your very own Private Beach & Dock

Annapolis, Maryland, United States

About this spacebrStunning Contemporary Home with private beach! House has been listed on another site receiving five star reviews from all previous guests. House was recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill & fire bowl. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.brThe spacebrThis gorgeous house sits at the mouth of the Severn River. The Severn River/Chesapeake Bay sits on the front side of the house and Chase pond (connects to the Bay) sits on the backside of the house. Water views from every room! The rooms have large expanses of glass to enjoy the views. Truly a unique setting.brbrThe site is perfect to watch the fireworks on the 4th, watch the blue angels during Naval Academy graduation weekend (they fly over the house and dock multiple times during their show), stay during the Annapolis boat shows, or a vacation/getaway with family or friends any time of the year. We have recently decided to list the house during Christmas and New Year's Eve. A wonderful spot to enjoy the holidaysbrbrWe are located in Annapolis. The location is ideal...3 miles to downtown Annapolis so you can visit but return to a peaceful location on the water.brbrThe beach is a perfect place to set up games. We have several games for the beach. If you have little ones, they will love to play in the sand. There is a fire pit on the beach with plenty of wood stacked if you wish to make a bonfire. Roasting sticks are in the kitchen. There are six beach chairs and beach towels. You can swim from the sandy beach or from the end of the dock. Gorgeous sand bottom at the end of the dock and shallow. We have a tree hammock next to the beach. This house owns well over half the private beach and another home owns the smaller portion of the private beach.brbrAt the end of the dock, the average depth is 2.5 feet. If you have a boat with a similar draw, please bring it and tie up. We have a launching site in the neighborhood. If you have jet skis, you are welcome to bring those too. Four large Adirondack chairs are affixed to the end of the dock. Please note, the water below the dock is shallow so do not dive. There is a ladder at the end of the dock that you can lower yourself into the water. All sand bottom at the end of the dock. brbrGreat sunrises and electronic blackout shades in each bedroom if you want to sleep in. Bedding in two rooms is by Restoration Hardware and the master bedroom has a custom made duvet cover and shams. All beds have down duvets and extra pillows are available in each room. All bathrooms have Restoration Hardware towels. The master bedroom has two super soft Restoration Hardware bathrobes and the other two bedrooms each have one bathrobe.brbrEnjoy the sunrises or sunsets from the dock. While enjoying the beautiful sunrises, you have the choice of enjoying a cup of coffee from the Nespresso Machine, the coffee press, and/or the coffee maker. We have a grinder too. There is an instant-hot tap if you would rather a cup of tea.brbrThe patio facing the Bay has a large grill with wonderful views of the Bay Bridge. We have comfortable Adirondack chairs on the patio. A wonderful place to enjoy the sunrise/sunset, your company while grilling and/or simply at the end of the evening.brbrThe designer kitchen has a sub-zero refrigerator/freezer, propane top 4 burner, 2 ovens, a built-in microwave and a dishwasher. Pots, pans, knife set, dishware, and glassware are new. With the open floor plan, you are able to enjoy your family or guests in the dining area or great room while preparing meals. We always have sugar, flour, olive oil for your convenience. There are also 3 bar stools at the kitchen counter. If you don't feel like cooking, I have a great list of restaurants.brbrThere is a beautiful office with built-in cabinets, a business chair, and large windows and glass doors with access to the back deck. If you need to get some work done, this is a great spot! Perfect for the business traveler.brbrThere are two propane fireplaces; one in the Great Room and one in the Master Bedroom. They will click on with a remote.brbrA generator, in case of a power outage, will kick on automatically and runs parts of the home.brbr4 smart TV's throughout the house.brbrWe are located in a quiet neighborhood at the end of a cul de sac/private drive.brbrThis is a smoke-free and pet free home. No exceptions.brNo parties, events, weddings and/or receptions allowed at the house. No Exceptions. The property is only for the guests approved and booked for the stay.brbrWe have many suggestions for fun activities in Annapolis. Once you book, please contact me via text or call if you would like suggestions on restaurants and/or help to pre-plan activities in Annapolis.brbrThree parking spots available.brbrPlease note: Any lighting of the fire pit and grill are at your own risk.brAny swimming or activities in the Bay are at your own risk. Do not swim in the pond.brDo not dive or jump from the dock; the water is shallow.brGuest accessbrAble to access entire house except for the garage. Room for 3 cars.br

3

Bed

3

Bath

6

Sleeps

$425.56

/ Nightly

Private Vacation Home

DTA Row Home | Walk to City Dock & The Yard

Annapolis, Maryland, United States

Summary:brbrStay on one of Annapolis's most iconic streets in this renovated 3-level row home. Walk out the door and you're steps from City Dock, Main Street, and USNA Gate 1. Sip coffee on the private balcony overlooking the Maryland State House, then head downstairs to the open kitchen and living area. Two bedrooms on the second floor, a loft with daybed and private full bath on the third, and a fenced patio out back. Smart TVs throughout, high-speed WiFi, and central AC. No car needed.brbrbrbrThe Space:brbrBEDROOMSbrbrTwo bedrooms on the second floor, each designed for comfort. The third-floor loft has a daybed and its own private full bathroom — great for extra guests or a quiet retreat.brbrBATHROOMSbrbrTwo full bathrooms with modern fixtures and bright finishes. Fresh towels provided.brbrKITCHENbrbrFully equipped with stainless steel appliances, cookware, dishes, utensils, and everything for home-cooked meals. Open layout connects to the dining and living areas.brbrLIVING AREASbrbrThe open-concept main level blends the kitchen, dining space, and family room — ideal for groups. Coastal touches and classic Annapolis character throughout. Smart TVs on every level. High-speed WiFi.brbrOUTDOOR LIVINGbrbrFenced back patio for outdoor dining or lounging. The private balcony off the loft has views of the Maryland State House dome — a genuinely special spot for morning coffee or evening wine.brbrPARKINGbrbrNo dedicated parking. Overnight parking is available in the Hillman Garage on Main St. In this location you won't need a car — everything is walkable.brbrLOCATIONbrbrSteps from City Dock, Main Street, and Gate 1 of the Naval Academy. Restaurants, bars, shops, and the waterfront are all within a 2-minute walk. This is the most walkable location in Annapolis.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrNo parking included

Bed

Bath

Sleeps

$373.6

/ Nightly

Apartment

Spa Creek Condo | Pool, Deck & Parking

Annapolis, Maryland, United States

Summary:brbrWake up to water views in this updated 1-bedroom Eastport condo overlooking Spa Creek. Step onto the covered deck to watch sailboats drift by, cool off in the community pool, or walk to Downtown Annapolis and USNA in minutes. The pullout sofa adds sleeping space for extra guests, and the full kitchen has everything you need. Two free parking spots right outside the building. A quiet waterfront home base for couples or small groups exploring Annapolis.brbrbrbrThe Space:brbrBEDROOMSbrbrOne bedroom with a plush bed, fresh linens, and closet space. The living room sofa pulls out into a queen bed for additional guests.brbrBATHROOMSbrbrOne full bathroom stocked with towels, soap, shampoo, and essentials.brbrKITCHENbrbrOpen kitchen with modern appliances, cookware, dishes, and utensils. Everything you need for meals at home.brbrLIVING AREASbrbrOpen-concept living space with beautiful views of Spa Creek. Smart TV and comfortable seating for relaxing after a day exploring Annapolis.brbrOUTDOOR LIVINGbrbrThe covered deck overlooks Spa Creek — furnished for outdoor dining or lounging by the water. Guests have access to the community pool (Memorial Day – Labor Day), shared dock, and waterfront common areas.brbrPARKINGbrbrFree parking for 2 cars directly outside the building.brbrLOCATIONbrbrIn the Yacht Club Condominiums in Eastport. Walk to Downtown Eastport restaurants — Boatyard, Adam's on the 4th, Carol's Creek. Cross the Eastport Bridge to Downtown Annapolis. Under 2 miles to USNA. About 3 miles to Navy Stadium.brbrbrbrGOOD TO KNOWbrbrbrbrCheck-in: 3:00 PM / Checkout: 11:00 AMbrbrSelf check-in with smart lockbrbrNo smokingbrbrPool hours vary by day brbrbrbrMonday, Wednesday, Thursday 4:00 - 8:00brbrCLOSED TuesdaysbrbrFriday 3:00 - 8:00brbrSaturday/Sunday/Holidays 12:00-8:00brbrbrbrGuest Access:brbrUse lockbox to enter the condo building. Door code to enter the unit. Walk in through the front door, go all the way through, towards the pool. Turn left to building A. Walk into building A and go up the stairs to A202.

Bed

Bath

Sleeps

$769.25

/ Nightly

Private Vacation Home

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Annapolis, Maryland, United States

Welcome to your 5 ⭐️ Annapolis home base for families, sailing crews, and group getaways. This spacious 4-bedroom home comfortably sleeps up to 12 guests and is located less than 5 minutes from the water and just 10 minutes from historic downtown Annapolis, the Naval Academy, waterfront dining, and local events. brbrCape St. Claire hosts its own July 4th parade and beach celebration — enjoy the morning festivities on foot, then head 10 minutes to downtown Annapolis for the harbor fireworks at 9:15pm before returning to the spacious firepit and basement bar to close out the night.brbrDesigned with groups in mind, the home offers plenty of space to gather, relax, and unwind. Enjoy a huge private backyard featuring a fire pit, cornhole, and a putting green—perfect for afternoons outside or evenings around the fire. Inside, the basement bar and entertainment area create an ideal space for nights in after a day on the water or downtown.brbrThe fully stocked kitchen makes hosting easy, with multiple appliances, all cookware and utensils, complete dishware, and a dedicated coffee bar with complimentary coffee and tea. A large dining area allows everyone to sit together comfortably for meals, games, or planning the next day’s adventures.brbrFor guests working remotely, the home includes a dedicated desk and fast Wi-Fi throughout. Free on-site parking and easy self check-in make arrival and departure simple. Pets are welcome with approval, making this a great option for families traveling with furry companions.brbrWhether you’re visiting for spring sailing events, graduations, weddings, or a weekend escape with friends, this home offers the space, comfort, and location to make your stay easy and memorable. Prime dates book quickly—early reservations are strongly recommended.brbr✦ What our guests love about our listing: ✦brbr-Check-in process: Keyless entry with codebr-Parking: Multiple-Car Driveway.br-OFFICE SPACE: Quiet area with spacious desk and comfy, supportive chair for remote work and extended staysbr-Coffee: Free K cups and Ground Coffee providedbr-Laundry: In unit washer and dryerbr-Queen-Sized Air Mattress for extra accommodationbr-Activities: Outdoor Firepit with Hammock, Regulation Size Cornhole Boards, and Indoor/Outdoor Putting Greenbr-Lightening fast WiFi on our two large 75 and four 55 SMART TV's.br-Four HUGE Queen Bed's with luxurious sheetsbr-Professionally cleaned and sanitized between each and every guest.brbrApproximate Travel times:br➤ Broadneck Park - 2 Minutesbr➤ Sandy Point State Park - 7 Minutesbr➤ Bay Hills Golf Club - 7 Minutesbr➤ Navy-Marine Corps Memorial Stadium - 10 Minutes ➤ Historic Downtown Annapolis - 11 Minutesbr➤ Annapolis Mall - 12 Minutesbr➤ US Naval Academy - 12 Minutesbr➤ Annapolis Landing Marina - 19 Minutes Landscaping occurs bi-weekly. Please understand they may perform service during your stay.brbrIf you want to be notified in advance, please inform us upon check-in.

Bed

Bath

Sleeps

$357.9

/ Nightly

Private Vacation Home

Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.

Annapolis, Maryland, United States

Immerse yourself in the rich history of Annapolis at our century-old home in Presidents Hill. With 3 bedrooms, 2 baths, and classic features, it's a cozy retreat and perfect home base for all there is to do in Annapolis.brbrWhether you're exploring historic streets, dining al fresco downtown, enjoying the waterfront activities, or here to cheer “Go Navy”, our home is the perfect base for your Annapolis adventure. brbrThis home is a 5 minute walk to everything in downtown Annapolis - USNA stadium, shopping, Main Street, museums, water taxis, waterfront dining, restaurants and more.brbrReturn home and relax in the charming backyard or curl up with a good book. Book today.br

Bed

Bath

Sleeps

$391.45

/ Nightly

Private Vacation Home

Modern Gem Near Historic Annapolis & Naval Academy

Annapolis, Maryland, United States

Built in August 2025 | Group-Friendly Layout w/ 4 En-Suite Bedrooms | 1 Mi to Shopping, Dining & HospitalsbrbrSpacious and stylish, this 4-bed, 4.5-bath home makes your Annapolis adventure feel effortless! Each en-suite bedroom offers a private place to recharge, while the open living room and patio offer space to gather. Shop at Annapolis Mall, tour the Naval Academy, or wander cobblestone streets of Historic Downtown, then return to a vacation rental designed with modern comfort in mind.brbr-- THE PROPERTY --brbrSTR-01110brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bedbr- Bedroom 4: 1 king bedbrbrTOWNHOME HIGHLIGHTSbr- Smart TVbr- Large dining tablebr- Private ensuite bathroomsbr- 2,600-square-foot interiorbr- Furnished balconybr- 2 floor-length mirrorsbrbrKITCHENbr- Refrigerator, stove/oven, dishwasherbr- Keurig, coffee & tea providedbr- Toaster, microwavebr- KitchenAid mixerbr- Cooking & baking basics, dishware & flatwarebrbrGENERALbr- Free WiFibr- Central A/C & heatingbr- Washer, dryer, laundry detergent/fabric softenerbr- Iron & board, drying rack, cordless vacuum cleanerbr- Linens & towels, shampoo & conditioner, body washbrbrACCESSIBILITYbr- Multi-level townhome, 2 steps to enterbr- Interior stairs required to access kitchen & living areasbr- Bedroom & bathroom on level 1brbrPARKINGbr- Driveway (2 vehicles)br- Free street parking (first-come, first-served) br- EV outlet available (bring your own charger)brbr-- THE LOCATION --brbr- 1 mile to Luminis Health Anne Arundel Medical Center & Children's National Hospitalbr- 2 miles to Navy-Marine Corps Memorial Stadium & Annapolis Mallbr- 3 miles to Annapolis City Dock & Historic District: dining, shops, museumsbr- 3 miles to United States Naval Academy & St. John's Collegebr- 9 miles to Sandy Point State Parkbr- 25 miles to Washington, D.C.br- 22 miles to Baltimore/Washington Int'l Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This multi-level townhome requires 2 steps to enter. There is a bedroom and a full bathroom on the 1st floor. Interior stairs are required to access the kitchen and living areas

Bed

Bath

Sleeps

$450.24

/ Nightly

Private Vacation Home

Dog friendly! Next to Navy Stadium and DTA Shuttle!

Annapolis, Maryland, United States

Enjoy your stay in our charming home centrally located directly across from Navy-Marine Corps Memorial Stadium on Taylor and in walking distance to downtown. For navy tailgating, you just can't get any closer! Upon your arrival, hang up your car keys and enjoy strolling through our quaint town or use one of the multiple transportation options. You're in the midst of it all!! We look forward to welcoming you to our home!brbrEnjoy our historic, cozy bungalow, built with love from our own grandfather's hands. A unique sandstone home built in 1920 with updates and comfort of 2020. A true gem nestled in the heart of Annapolis! Read a book in the rockers on the screened in porch or light a fire and relax by the Solo Stove firepit on the patio. Whether you prepare your dinner on the grill outside or in the spacious, well lit and well appointed kitchen, you'll enjoy every aspect of this house and will feel right at home during your visit!brbrA terrific place to walk or run! A wonderful, paved, mile long trail awaits you directly across the street at the stadium. Or you may walk 1/2 mile to the Arts District on West St. or 1/4 mile to West Annapolis- both locations offering restaurants and some boutique shopping. Historic Annapolis and the top of Main St is only a mile away offering more shops and eateries! We have left recommendations of some of our favorite places in the guidebook at The Bungalow.brbrWe live adjacent to the property and can be as available as needed during your stay. Outdoor maintenance and yard work is ongoing and may take place during your stay. However, it will not take place without first discussing with you, our guest, as we do not want to impose upon your stay or interrupt any activities you may have planned.brbrGuests have access to the upper level of the home as well as the laundry. The laundry is in the lower level along side of the garage. The owner has tools in the garage that are not to be used by the tenant. The owner may access these tools through the garage door which is a separate entrance than that which the tenants use for accessing the home.

Bed

Bath

Sleeps

$952.41

/ Nightly

Private Vacation Home

Annapolis/Eastport 4 BR w/ Game room - Walk everywhere!

Annapolis, Maryland, United States

This is the perfect house for your family friendly visit to Annapolis, MDbrbr*Please no bachelor/bachelorette partiesbrbrEnjoy everything the sought after Eastport neighborhood has to offer. Very short walk to bars, restaurants, shops and even a brewery!brbrCity Dock/Ego Alley is less than one mile away & the Navy Yard is 1.1 miles away. brbrComing in for a Navy game The Stadium is 2.3 miles (9 min drive)brbrOur house has a fenced in yard, with two patio areas and two fire pits. brbrEnjoy playing pool, shuffleboard and darts in our game room!

Bed

Bath

Sleeps

$299.82

/ Nightly

Private Vacation Home

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Annapolis, Maryland, United States

Enjoy the close proximity to all Annapolis has to offer at this row house located next to college creek. Nicely decorated and cozy! There is a queen bed in each room as well as a sofa which folds into an additional queen bed. The yard offers seating and a charcoal grill and there's a balcony off the bedroom for private outdoor enjoyment. Home is equipped for cooking and hanging out if you prefer to stay home. But if you are out on the town enjoy the ease of only a 10 minute walk to West Street where you will find great restaurants and church circle. Only 20 minute walk to the naval academy and downtown so we park the car in the house's own parking in the rear off the street. No need to fuss with parking downtown! If in town for a Navy game, the Stadium is only a 10 minute walk.

2

Bed

1

Bath

6

Sleeps

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