Vacation Home Rentals By Owner In Annapolis, MD

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWelcome to your Annapolis getaway! Situated on an expansive and rare 1/2 acre homesite, this beautifully preserved home blends historic charm with modern amenities—perfect for families, friend groups, or Navy families visiting town. brbr brbrInside, the main level features two spacious king bedrooms, a full bath, a sun-filled living room, and a delightful four-seasons sunroom—ideal for morning coffee, evening wine, or movie nights on the big-screen TV. brbr brbrUpstairs, you'll find three additional bedrooms, including a generous combo guest room (with an additional sitting room/bedroom). There’s also a shared full bath and a full laundry room. The entire home has recently been updated to include a modern HVAC system with mini splits and remotes in each bedroom and gathering space. brbr brbrSleeping Arrangements 5 Bedrooms, 2 Baths (Sleeps 12): brbrSecond Floor brbrFamily Pink King Bedroom: King bed + Twin plus Twin Trundle brbrTan & White Guestroom: King bed brbrGray Guestroom: King bed brbrFull bath in the Second Floor Hallway brbr brbrMain Floor brbrBlack & White Guestroom: King bed brbrAnchor Guestroom 2: King bed brbrShared full bath on the Main Floor hallway brbr brbrHome Highlights: brbrFully equipped kitchen with stainless steel appliances brbrMultiple hangout spaces with Flatscreen TVs: Living room, and Four-seasons sunroom with flatscreen Smart TV brbrHigh-speed WiFi + 3 large Smart TVs brbrDriveway parking for multiple vehicles brbrWasher/dryer for guest use brbrLuxury linens + complimentary starter toiletries and paper products brbrDog-friendly (with $150 non-refundable pet fee per pet) brbr brbrLocation - Walkable to it all! brbrNavy-Marine Corps Memorial Stadium – 0.7 miles brbrU.S. Naval Academy – 1.8 miles brbrDowntown Annapolis shops & restaurants – 1 mile brbrWashington, D.C. – 32 miles brbrBaltimore – 31 miles brbrSkip the parking hassles and walk to parades, festivals, farmers markets, waterfront events, and cozy cafes. You’ll love being in the heart of it all—without ever needing your car. brbr brbrHouse Rules: brbrPrimary renter must be 25+ brbrNo parties, smoking, or events brbrQuiet hours must be observed brbrCheck-in: 4:00 PM | Check-out: 11:00 AM

Historic Charm Meets Walkable Convenience in the Heart of Annapolis with Parking

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$655.5

Walk downtown or to grocery, restaurants, etc. We live in a nice modernly decorated duplex adjacent to Navy Stadium. It is a close-proximity neighborhood. We live in one half (it is our primary residence but i rent it sometimes to make extra income as a disabled veteran) & someone else lives in other but there's a privacy fence & all amenities listed are ours only. It is an easy walk to all the popular sites. We've unlimited, free parking & many, many amenities. We've lovely deck w/ built-in fireplace, hot tub & relaxing furniture. Backyard is a fantastic, fun place for whole family. There’s ping pong, bocce, cornhole, horseshoes, tic-tac-toe. There's an outdoor bar w/flat screen tv, so you can watch movies or games from hot tub. Upstairs from main level king master bdrm (ensuite w/ full bathroom) , 2 bdrms w/ queens (one w/ a TV) as well as full bath in hall. On main level theres a kitchen w/ small table/chairs, dining w/ seating for 8-10, living area w/electric fireplace, massage chair, sofa, smart TV, bluetooth speakers & enough seating for 10. No bedrooms on main level (must use stairs). There's also a 1/2 bath. Downstairs to lower level is a hall with lots games, books & crafts. 3 rooms on lower level.- a laundry area w/ washer, dryer, extra frig & lots of storage w/ extra pillows, sheets, party supplies, etc. On lower level there’s a room w/ queen bed. 3rd lower level room has two double futons that can be opened as bed for 2 or used by one as is. Theres a small exercise area w/peloton, yoga eqpt, weights,bands, etc. Lots of games, dart board, a music area w/ guitar, keyboards, karaoke , etc. Amenities incl exercise eqpt, peloton, bikes, vitamix, Wi-Fi, several TV's , dining table seats 8, 2 frig/freezers, blankets, coolers, tons games, towels/pillows, picnic stuff, etc. hardwood floors on main/upper floors. We've hosted hundreds in our home & love providing a great vacation experience. This is NOT a party house - it is for nice family gatherings or relaxing getaways w/ few close friends. You many Not have any parties or events without our advance permission - If we get noise complaints we have the right to remove you from the premises. WE WILL NOT TOLERATE UNAUTHORIZED GUESTS OR PARTIES.brbrIMPORTANT INFO - In case of questions/concerns during stay – call/text Laurie 443.994.0835.

Lots free parking, hot tub, outdoor oasis - NOT party house

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$387.6

New Outdoor Space for 2026! Enjoy sunrises on the newly built porch. A great space for morning coffee or to spend an evening outdoors. This upscale 2 bedroom, 1 bathroom water view cottage is located in a private beach community off of the Chesapeake Bay. Whether you're looking for a place to relax and recharge or to enjoy water sports, this is the place for you. Just a 5 minute stroll and you’re on the beach or curl up and enjoy the cozy interior of this home. Kitchen has everything you need to prepare meals or store leftovers from one of many nearby restaurants. Located on the shores of the Chesapeake Bay, this property is only 5 miles from downtown historical Annapolis and 35 minutes from Washington DC. Just the spot for a relaxing getaway on your own or a fun packed time with family and friends. This community offers a variety of activities from water sports to beach volleyball. Want to keep up with your exercise routine, try our 1 mile, three station exercise circuit course. Want to take your canoe/kayak out, you have access to the water at the boat ramp just a short walk away. A kid and pet friendly neighborhood with playgrounds and doggie stations nearby for your usage. Check out the video for more information about the neighborhood. Welcome home to The Anchors!

Cozy Cottage by the Beach - Waterview
Minutes from Downtown Annapolis

Annapolis, Maryland, United States

2

Bed

1

Bath

Sleeps

$808.19

Looking 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 KNOW

2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace

Annapolis, Maryland, United States

Bed

3

Bath

8

Sleeps

$893.59

Conveniently located in the Historic District of downtown Annapolis, this two-story retreat is perfect for families and friends looking for a convenient location with parking to immerse yourselves in the history of Annapolis. This prime location situates you two blocks from Maryland State House, three blocks from City Dock, and four blocks from USNA. Other great attractions include Watermark Tours, Charters, Cruises, Rams Head On Stage, Banneker-Douglass Museum, Jonas and Anne Catharine Green Park, Quiet Waters Park, and more.brbrThis historic home features living areas that will take you back in time to life in 1900 Annapolis, yet offers basic modern amenities. The kitchen and dining area surround an original brick fireplace with plenty of space and all you need for preparing treats for the crew. The private sunroom with comfy sofas and a desk look out over the brick courtyard. Curl up on the sofa and enjoy a fun book or an entertaining movie or show on the smart TV with cable and streaming. The fully-appointed kitchen has been updated and has all the essentials for you to prepare delicious homemade meals and treats for the crew. Outside, you will discover a small side/backyard for outdoor enjoyment and dining alfresco.brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.brStreaming is available using your own accounts.brThe wood fireplace is ornamental only and not for guest use.

Historic downtown townhome with brick courtyard, sunroom & parking

Annapolis, Maryland, United States

3

Bed

2

Bath

6

Sleeps

$1417.8

Find gorgeous gathering spaces inside and out at this light-filled three-story waterfront home on a protected inlet of the Chesapeake Bay. Here in Bay Ridge, you'll have a private dock, access to the bay beaches, and a stunning setting for family vacations and special holidays. You'll be within five miles of historic downtown Annapolis, home to charming shops, great eateries, and the U.S. Naval Academy.brbrSpend sparkling summer days outdoors, where several beautiful spaces await you. Sip your first cup of morning coffee in an Adirondack chair on the deck, taking in a serene view of the bay below. Launch your kayak from the dock, watch your kids play in the gently sloped backyard, and gather for evening barbecues on the shaded patio beneath the deck. One of the guest bedrooms boasts direct patio access.brbrAs you step inside the front door, you'll be greeted by a grand spiral staircase and a wall of windows framing the lake. One of Annapolis' leading interior designers recently renovated the entire home. At the heart of the house is a two-story great room with generous seating, a smart TV, and doors that lead outside to the deck. To one side of the great room sits a formal dining room and a wet bar for entertaining. To the other is an expansive kitchen overlooking the lake with stainless steel appliances, including an in-island gas stove, a light-filled breakfast nook, and a full laundry room. Step into the hot tub and simmer as you relax your body.brbrOther notable features can be found at every turn, including a private home office for remote work, a huge den downstairs with another smart TV and kitchen, a quiet room for yoga, and a fantastic game room with air hockey, foosball, and a game table. brbrTHINGS TO KNOWbrStreaming services are available with guests' own account credentials.brSmoking is prohibited on the property.brThe gas fireplace is not operational.

Beautiful waterfront home on The Chesapeake Bay with private dock & beach access

Annapolis, Maryland, United States

5

Bed

3

Bath

10

Sleeps

$496.99

This bright and inviting vacation home provides an ideal escape for a romantic couple's getaway or a family excursion, allowing you to explore all the attractions Annapolis offers. brbrNearby, you'll find popular destinations such as Annapolis City Dock, Rams Head on Stage, and the U.S. Naval Academy Museum. Enjoy strolling along the city's waterfront, watching live music, and exploring historical museum exhibits. brbrThis multi-level retreat features artfully decorated interiors and great outdoor space for entertaining, grilling with friends, or gathering for laughs around the firepit. Not to mention, rooftop access provides incredible views of the surrounding city! The deluxe kitchen boasts stainless steel appliances and ample dining space - perfect for any home chef crafting delicious meals. The bedrooms, furnished with luxurious linens and cozy blankets, offer a comfortable sanctuary for streaming your favorite movies and unwinding after a fun day exploring your new city. brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM.brNo smoking is permitted anywhere on the premises.

Gorgeous & bright retreat with patio, firepit, W/D, & stunning rooftop views

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$750.59

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrAvailable for Commissioning Week 2025! brbr brbrCharming 1905 Eastport Duplex: Historic Character Meets Modern Comfort brbrStep into a beautifully-preserved piece of history with this charming 1905 duplex in the heart of Eastport. Offering a seamless blend of old-world charm and modern amenities, this home is perfect for families, professionals, or anyone seeking a cozy, yet stylish getaway. brbr brbrMain Floor: The spacious open layout on the main floor includes a large living area, a dedicated office/desk space, and a convenient powder room. The inviting dining area opens to a gourmet kitchen, fully equipped with stainless steel appliances, perfect for cooking up a feast. The main floor also features a private, fenced backyard, ideal for relaxing or entertaining. brbr brbrUpstairs: Two generously-sized King bedrooms provide a restful retreat, complete with luxury linens and a shared full bath. One bedroom boasts a private balcony overlooking the serene backyard and the front King bedroom has its own flatscreen TV and desk space. A bonus loft space offers additional room for kids or younger families to relax and enjoy their own shows. brbr brbrAdditional Features: brbrParking for up to 3 cars brbrPrivate fenced backyard with a patio deck and and gas fire pit brbrCovered front porch, perfect for enjoying the neighborhood brbrGas grill (propane included) brbrHigh-speed WiFi and a big-screen TVs for entertainment brbrDedicated workspaces on each level for remote work or study brbrFull washer & dryer for your convenience brbrDog-friendly brbr brbrPerfect Location: Situated just steps away from Eastport's vibrant cafes, restaurants, and bars, this home offers easy access to everything the neighborhood has to offer. Water access for paddle boarding and kayaking (BYO) is just a short stroll away. brbr brbrPlus, you're only: brbr1.5 miles from the U.S. Naval Academy brbr30 miles from Washington, D.C. brbr25 miles from Baltimore brbr brbrHouse Rules: brbrNo smoking, parties or events brbrDogs ok if $150/per pet fee paid prior to checkin brbrMust be 25+ to book brbrCheck-in: 4:00 pm | Check-out: 11:00 am

Charming Eastport Home with Modern Comforts & Parking Dog-Friendly & Steps to Shops with Backyard

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$561.01

Pet Friendly w/ Fee | Home Office Space | 7 Mi to United States Naval Academy brbrExperience the best of Maryland when you stay at this 4-bed, 3.5-bath vacation rental. With a lakefront beach, a shopping center, and a sprawling park just a short walk away, this family-friendly home offers plenty to do nearby! Ready to venture out Visit the scenic shores of Sandy Point State Park, enjoy waterfront adventure along the Chesapeake Bay, or explore the charming historic district in downtown Annapolis.brbr-- THE PROPERTY --brbrSTR00593brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Bedroom 3: 1 queen bedbr- Bedroom 4: 1 queen bedbrbrOUTDOOR LIVINGbr- Private balcony w/ seatingbr- Back deck, dining space w/ umbrellabr- Fenced-in backyard, charcoal grill (charcoal provided)br- Nearby public lake w/ kayaks & canoesbrbrKITCHENbr- Refrigerator, stove/oven, microwave, hot platebr- Keurig coffee maker (coffee provided), blender, slow cookerbr- Cooking basics, toaster, toaster oven, rice cookerbr- Dishwasher, dishware/flatware, paper towels/trash bagsbrbrINDOOR LIVINGbr- 4 Smart TVs, gas fireplacebr- Bar-top seating, breakfast nook, formal dining roombr- Dedicated office space, board games, booksbr- Walk-in closets, jetted tub, ceiling fansbrbrGENERALbr- Free WiFibr- Central air conditioning & heatingbr- Washer & dryer, laundry detergentbr- Linens & towels, hangers, iron/boardbr- Complimentary toiletries, hair dryerbr- Keyless entrybrbrFAQbr- 3 exterior security cameras (facing out)br- Pet fee (paid pre-trip)brbrACCESSIBILITYbr- Stairs required to access, 3-story homebr- No bedrooms or full bathrooms on 1st floorbrbrPARKINGbr- Driveway (9 vehicles)br- RV/trailer parking available on-sitebrbr-- THE LOCATION --brbr- Walkable to public lake, beach, boat ramp, park & shopping centerbr- 2 miles to Broadneck Parkbr- 4 miles to Sandy Point State Park & Baltimore Harbor Lighthousebr- 7 miles to downtown Annapolis: historic landmarks, restaurants, shops, live entertainmentbr- 21 miles to Baltimore/Washington International Thurgood Marshall 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- Pet friendly w/ $50 fee (+ fees & taxes, 2 max)br- No events, parties, or large gatheringsbr- Must be at least 22 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This 3-story property requires exterior stairs to enter. Interior stairs are required to access all bedrooms and full bathrooms on the upper levelsbr- Your safety matters. This property features 3 exterior security cameras. Camera 1 is a Ring doorbell camera located next to the front door facing the front entrance area, camera 2 is located over the back door facing the back entrance, and camera 3 is located over the basement door facing the basement entrance. The cameras are outward facing and do not look into interior spaces. The cameras record video and audio continuously

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$609.83

Welcome to our retreat in Annapolis. The place is located minutes from downtown and the Naval Academy, in the neighborhood of Cape St Claire, known for its beaches and the family-friendly atmosphere.brbrAs you enter, you are greeted from the main floor with outdoor views of the back deck. Gather with your family and friends in the kitchen for quick bites or elaborated meals to be enjoyed at the dinning table. Sit and watch your favorite shows in the living room or enjoy a conversation with loved ones while looking at the breathtaking views of the front yard. Better yet, retreat into one of three bedrooms on this floor. Each has a comfortable bed dressed with soft sheets, blankets and plenty of pillows to ensure you get plenty of rest and wake up invigorated. The master bedroom is spacious and has its own ensuite. A second full bathroom is located in the hallway.brbrAnother favorite gathering spot is the larger family room on the lower level. A third full bathroom is also on this level and is situated next to the fourth bedroom. This bedroom is the largest. It has two queen beds and a full bed. The driveway can hold up to five cars. brbrA short drive will take you to the community beach with a playground which is open during summer months. Several restaurants are located within a mile. brbrWhether you are planning a quick getaway or in town for a celebration, our home and community offer the space and amenities you need to make your stay an unforgettable experience. brbrWelcome Home! We look forward to hosting you.

Your Annapolis Retreat near the Naval Academy and downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$778.67

This is one of the most charming houses in Murray Hill! Located on a dead end street, this brick colonial with a slate roof sits on a beautiful lot just 1/2 block from Spa Creek. This beautifully updated 2449 sf home located in the City of Annapolis boasts 4 bedrooms (two bedrooms with king beds), and 3.5 baths. It was completely renovated in 2016 to become a lovely vacation rental for up to 8 guests. There are no personal belongings in the home so you are not dealing with any clutter and it was set up 100% with guests in mind to enjoy. This approach along with our ammenties has helped us earn our 94 five star reviews. brYou can park the cars in our off street driveway which is big enough to park 3 cars and walk everywhere. This means all your guests have freedom and autonomy to come and go. brThe house is located approx a 1/2 half mile from the top of Main Street. The home has hardwood floors throughout, tons of natural light, new kitchen with SS appliances, huge center island, 2 ovens, granite countertops and a family room off the kitchen with a built-in wine refrigerator. Our home is fully furnished with linens, dishes, cookware, and we provide other sundries like: coffee, sugar, Splenda, PAM, olive oil, baggies, Reynolds wrap, salt and pepper, shampoo, body wash, conditioner so there is no need to hurry up and run to the store when you get here! brbrThe home boasts 3 55-inch smart LG tv's. The master bedroom is huge (18x15) with a king bed, and a 55-inch LG tv. The master bath has a corner soaking tub, separate vanities and a luxurious shower that has 2 shower heads, 3 body sprays and a built-in bench for a spa like experience. brbrTwo additional bedrooms and one full bath are located on the 2nd floor. Bedroom #2 has a queen bed and bedroom #3 has two XL twin beds that can be put together to make a king. The 4th bedroom is located on the lower level and has its own private bath. brRelax in the screened-in porch or grab a book and either a cup of coffee or a glass of wine and walk approx 400 feet away to sit by the water's edge at Old Woman's Cove off (Spa Creek) and chill.brNote: The renter who signs the lease MUST occupy the property. There is no subletting allowed.

100 5-star Reviews located in the City of Annapolis in a quiet neighborhood!

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$386.82

Summary:brbrJust minutes from Sandy Point Beach and a short 15 minute drive to the US Naval Academy, this 4 story home has everything you need to enjoy your stay. You will find a peaceful and tranquil setting to relax and unwind on either one of the decks or around the fire-pit. Relax and watch TV in multiple living room spaces or retreat to the master bedroom suite which has its own private deck. A huge bonus room on the 4th story loft area, is perfect as dedicated workspace or room for guests to stay!brbrbrbrThe Space:brbrWelcome to your home away from home! We can't wait to provide you with an unforgettable experience. Whether you seek relaxation or want to go Downtown to enjoy the views or visit the US Naval Academy, this home provides the perfect location. brbrbrbrOur 4-story home is designed for comfort and connection, comfortably accommodating up to 8 guests.brbrbrbrKey Features:brbr* Main Level: An open-concept floor plan with a fully equipped kitchen, a dining area for six, and a cozy family room with a plush couch, large Smart TV, and a warm fireplace.brbr* Lower Level: An additional living room complete with plenty of board and card games, with direct access to the outdoor fire pit.brbr* Outdoor Decks: Unwind in the private hot tub located on one of the home's decks.brbr* 4th-Story Loft: A huge bonus room that serves as a dedicated workspace or a private suite, featuring its own TV and a sleeper sofa.brbrbrbrWhere You'll Sleep:brbr* Master Bedroom (2nd Floor): A serene suite with a queen bed, large Smart TV, a spacious en-suite bathroom, and a private patio.brbr* Bedroom 2 (2nd Floor): Features comfortable and cozy bunk beds and beautiful natural light.brbr* Bedroom 3 (2nd Floor): Offers a queen bed with plenty of storage space. Bedrooms 2 and 3 share a full bathroom in the hallway.brbr* Loft (4th Floor): A comfortable sleeper sofa that opens to a queen bed.brbrbrbrbrbrPlease respect the neighbors and neighborhood. brbrNo parties or events of any kind without prior coordinationbrbrbrbrProperty Distance to:brbrUSNA: 7.1 milesbrbrNavy and Marine Corps Memorial Stadium: 7.1 milesbrbrbrbrGuest Access:brbrGuests will have private access to the entire 4-story townhouse during their stay. This includes all bedrooms, living areas, the kitchen, decks, and private hot tub.brbrbrbrAdditionally, you are welcome to use the shared community amenities:brbr* Tennis Courtbrbr* PlaygroundbrbrbrbrEntry is seamless with self check-in using a smart lock. You will receive your unique access code prior to arrival.brbrbrbrGetting Around:brbrA car is recommended for getting around the area.brbrbrbrOther Things to Note:brbrThere are two dedicated parking spaces available to you. All other parking is located on the street and is free.brbr* Security: For your safety and security, there are exterior security cameras located on the property.brbr* Check-in: This is a self check-in property. Detailed instructions and your access code will be sent prior to your arrival.brbr* Registration Number: 000794brbrbrbrInteraction with Guests:brbrWe prioritize your privacy and comfort. The home is set up for self check-in, and we will not be present during your stay. We are readily available and responsive via the messaging app should you have any questions or need assistance.

Annapolis Spacious Family Retreat

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$199.75

STR-270 - This fully furnished 4-bedroom, 3-bath Annapolis home is available for mid-term stays of 120 days or more and is ideal for relocation, military, corporate, and temporary housing needs. Located in the quiet Pendennis Mount neighborhood just across the USNA Bridge, the home offers a peaceful residential setting with easy access to downtown Annapolis, shopping, dining, commuter routes, and the Naval Academy area.brDesigned for comfortable extended stays, the home features a welcoming main living area with hardwood floors, a fireplace, and a flat-screen TV. Sleeping arrangements include a king bed in the primary suite, queen beds in two additional bedrooms, and a twin bed in the fourth bedroom. A finished basement provides another queen bed, valuable extra space for work, recreation, storage, or flexible day-to-day living.brbrGuests will also enjoy off-street parking for up to three cars, a back deck with gas grill, and a small fenced yard for approved pets. Located in the Broadneck School District, this home is a practical and comfortable option for families, professionals, and households needing furnished housing in Annapolis for several months or longer. A separate self-contained upstairs apartment at 2 Ritchie Road may also be available for additional accommodations.

Extended-Stay Annapolis Home Near USNA & Downtown

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$493.8

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrHow many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite) ! brbr brbrJust 1-2 blocks from the Annapolis waterfront, the State Capitol, restaurants, shopping and the Naval Academy, this cherished property is registered with the Historical Society of Annapolis (originally home to “Sam’s Grocery”—a beloved neighborhood corner-store). brbr brbrAfter Sam's Grocery closed up shop in the eighties, the building was converted into a bed and breakfast, most recently called the Chez Amis Inn. Now its a unique rental home and you have the entire place to yourself! Each of the three upstairs bedrooms has been named by the former innkeepers and they are a tribute to the State Capitol's history. On the main floor you will find the Treaty of Paris Room-a library with an en Suite bath and Full size Sleeper sofa. brbr brbr**Parking is not on premises!! A dedicated parking spot at nearby garage (15-minute walk from the house) is provided. Please contact us for details. brbr brbrSLEEPING ARRANGEMENTS 4 BR / 4 BA / Sleeps 7 brbrThe State House Bedroom: brbr-King Size Bed brbr-En Suite Bathroom brbr-Extra Pedestal sink in bedroom brbr-Wall mounted TV brbr brbrThe Law Library: brbr-En Suite Bathroom brbr-Queen Bed brbr-Wall mounted Flatscreen TV brbr brbrThe Annapolis Room: brbr-Queen bed brbr-Private Bathroom in Hall brbr-Wall mounted Flatscreen TV brbr brbrThe Treaty of Paris Den: brbr-Multi-functional Family Den and Bedroom brbr-Full Size Sofa Bed brbr-En Suite Bathroom brbr-Wall mounted Flatscreen TV brbr*The full-size sofa bed may be tight for 2 guests. There is also a portable Twin cot located in the home. brbr brbrHIGHLIGHTS: brbrStocked kitchen with every appliance - large and small - you would need. brbr-Fully-stock Bar in the Library - BYO liquor/spirits brbr-Kitchen Coffee bar seats 2 brbr-Dining room table seats 8 brbr-Outside seating for 4 brbr-High Speed Internet and WiFi brbr-Big Screen TV in Main Floor Library (Flatscreen TVs in every Bedroom) brbr-Luxury linens, complimentary toiletries and paper product Starter Kits, and boutique-level service. brbr-Washer & dryer located inside the home. brbr-Dogs allowed with $150 non-refundable pet deposit paid prior to check-in. brbr-One Garage Parking Spot located 0.7 miles from the home. brbr-Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. brbr brbrProperty Distance to: brbr-U.S. Naval Academy – 1 block brbr-Washington, DC – 30 miles brbr-Baltimore - 25 miles brbr brbr* Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. brbr* All beds are ready made for you with freshly laundered sheets & towels. brbr brbrHouse Rules brbrReservations 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. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. brbrCheck-in time: 4:00 pm brbrCheck-out time: 11:00 am

Walk to USNA, Main St w Parking Historic Wisteria

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$731.25

From the minute you walk in the door, you will feel the warmth and charm this home offers. brbrLocated on the Eastport side of Spa Creek, but only 2 blocks to the Annapolis Bridge, this well appointed home is used exclusively for vacation rentals so you are never competing with the owner's belongs tucked away for your visit. But unlike many other rental property in the area, this home is equipped to live in, and is a well stocked home with high quality amenities.brbrLocated along 'restaurant row', you are steps from some of the best restaurants in Annapolis. Or, walk the .5 miles to be in the heart of downtown Annapolis. With a two car driveway, parking is never an issue. brbrThis house was recently renovated with a light nautical feel, beautiful artwork, quality furnishings and comfort that you will want to come home to. Whether your first visit to Annapolis, or you are a frequent visitor taking advantage of Annapolis' wonderful sailing and Naval Academy, this is a home you will want to keep coming back to!

Nautical Feel to This Beautiful Eastport Home

Annapolis, Maryland, United States

Bed

Bath

Sleeps

$665.43

Experience the Difference: Professionally Managed by iTrip AnnapolisbrbrWaterfront Oasis with Private Dock, Firepit & Kayaks brbrWelcome to the Pearl of Oyster Harbor – a tranquil waterfront retreat on the Annapolis Neck Peninsula. This charming cottage offers the best of all worlds: stunning natural beauty, water activities, and modern comforts. brbr brbrOutdoor Features: brbrPrivate dock for boating, kayaking (3 total kayaks: two adult and one youth), or paddleboarding (inflatable SUP included) brbrExpansive lawn perfect for cornhole, yard games, or simply soaking up the view brbrFirepit for cozy evenings with s'mores and stories brbrHammock for relaxing with a good book or simply enjoying nature brbrParking for 3-4 cars on the driveway brbr brbrIndoor Highlights: brbrBright, airy sunroom with harbor views for board games and family time brbrSleek, modern kitchen with large picture windows framing the waterfront brbrLiving room featuring a smart TV and gas fireplace for cozy evenings brbrSmall desk and WiFi printer for remote work convenience brbr brbrNeighborhood amenities: brbrSwimming beach brbrExercise: Beach volley ball court, 1-mile exercise circuit course, 12' climbing wall, 16' rope climb, brbrFishing pier and boat ramp brbrPlaygrounds, nature preserve, picnic areas, beach gazebos brbr brbrStarter Amenity Pack: brbrWe've got you covered with essentials to make your stay stress-free, including: brbrCoffee, sweeteners, dish soap, and paper towels brbrSoap, shampoo, conditioner, and hand sanitizer brbrFreshly-laundered sheets and towels for every guest brbr brbrSleeping Arrangements (3 BR / 2 BA, Sleeps 8): brbrFront Queen Bedroom: Queen bed, shared full bath in the hall brbrWaterfront Bedroom: Full bed, shared full bath in the hall brbrBunk Bedroom: Twin bunk beds (two twins), shared hall bath brbrLoft: Full bed above the living room brbr brbrHouse Rules: brbrFamily rentals only; one guest must be at least 25 years of age brbrNo smoking, parties, or events brbrQuiet hours from 9:00 pm to 8:00 am brbrDogs allowed with $150 per pet non-refundable fee paid prior to checkin. brbrCheck-in: 4:00 pm | Check-out: 11:00 am brbr brbrProperty Distance to: brbr-Downtown Annapolis – 4 miles (10 mins) brbr-U.S. Naval Academy – 4.5 miles (12 mins) brbr-Washington, DC – 35 miles brbr-Baltimore - 20 miles brbr brbrCreate lasting memories at The Pearl (of Oyster Harbor), where waterfront tranquility meets thoughtful amenities and outdoor fun. Book your stay today for an unforgettable Chesapeake Bay escape!

Waterfront Home with Private Dock, Community Beach

Annapolis, Maryland, United States

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STR-270 - This private 2-bedroom apartment in Annapolis is a smart choice for mid-term renters seeking a clean, comfortable, and budget-friendly stay near downtown. Well suited for corporate housing, traveling nurses, military assignments, relocations, and temporary housing needs, this second-floor apartment offers privacy, parking, and a convenient location just across the Naval Academy Bridge.brThe apartment is fully self-contained above a single-family home and features its own private entrance, sidewalk access, and off-street parking from Ritchie Road. Guests enjoy a quiet residential setting while staying close to downtown Annapolis, the U.S. Naval Academy area, major commuter routes, and local amenities.brInside, the space is organized, spacious, and easy to settle into for an extended stay. Outside, a small front yard offers room to relax, and the nearby B&A Trail provides easy access to walking, biking, and outdoor recreation.brThis is an excellent fit for traveling professionals who want dependable extended-stay housing in Annapolis without the traffic and congestion of downtown living. Pets are welcome on a case-by-case basis. The lower level of the home is available as a separate rental.

Private 2BR Apartment with Parking for Corporate, Medical & Military Stays

Annapolis, Maryland, United States

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$1405.24

STR-250 -Escape to this spacious waterfront home in Arundel on the Bay, where sweeping Chesapeake Bay views surround you on three sides. With 5 bedrooms and 3.5 baths, this coastal retreat is ideal for families and groups looking to relax, reconnect, and enjoy life by the water.brInside, the open layout offers plenty of space to gather for meals, conversation, and downtime together. The main-level primary suite features a king bed and private bath, while the additional bedrooms offer flexible sleeping arrangements for kids, couples, and extended family.brStep outside to enjoy the wraparound deck, with both screened and open-air spaces for morning coffee, outdoor dining, and evening sunsets over the bay. The large yard provides room for games and family fun, and the community beach is just a 1-minute walk away.brLocated in the peaceful waterfront community of Arundel on the Bay, this home feels private and relaxing while still being just a short drive from downtown Annapolis, with its restaurants, shops, and local attractions.brWhether you’re planning a summer vacation, a family gathering, or a quiet waterfront escape, this Chesapeake Bay home offers the space, setting, and views to make your stay memorable.--PLEASE NOTE: NO large parties or events of any kind are permitted at this home.--------

Panoramic Bay Views, Wraparound Decks, 1-Minute Walk to Beach

Annapolis, Maryland, United States

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$1489.52

STR000259 - Just minutes from downtown Annapolis, this stunning waterfront home offers a private, upscale retreat for up to 8 guests. Located in a quiet residential neighborhood, the property combines modern design, spacious indoor living, and beautiful outdoor spaces for a memorable stay on the water.brInside, the home features soaring ceilings, light-filled living areas, and sweeping waterfront views. The gourmet kitchen is equipped with a six-burner stove, three dishwashers, and wine storage, and opens to a comfortable family room with easy access to the deck and pool area. A formal dining room provides an elegant setting for meals with family and friends.brbrThe home offers 4 spacious bedrooms, each with its own en-suite bathroom. One guest bedroom is located on the main floor, ideal for those who prefer fewer stairs. Upstairs, the primary suite features vaulted ceilings, a private balcony with panoramic water views, and a spa-like bathroom with a soaking tub, shower, bidet, and Finnish sauna. Two additional upstairs guest suites offer designer bathrooms and generous closet space.brbrGuests will also enjoy a large recreation and TV room with a pool table, piano, treadmill, Pilates machine, free weights, and balcony access overlooking the pool and water.brbrOutside, the beautifully landscaped grounds are designed for relaxing and enjoying the setting. The contemporary pool is open from Memorial Day through Labor Day and is surrounded by multiple seating areas, waterfront decks, and peaceful garden spaces. A Big Green Egg, gas grill, outdoor dining area, and copper fire pit make it easy to enjoy time outdoors from morning coffee to evening gatherings.brbrFor those who love the water, the property includes a private dock and pier, 4 kayaks, 2 paddleboards, and 2 bikes for exploring the area. Parking is available for up to 6 cars, and a full-size washer and dryer are located on the main floor for added convenience.brbrThis home is ideal for families and small groups seeking a relaxing waterfront escape with easy access to Annapolis dining, shopping, and attractions. Please note that this property is located in a peaceful residential community and is best suited for respectful guests looking to enjoy the home and surroundings.brImportant to note: This waterfront property includes a pool, dock, pier, kayaks, and paddleboards. Use of these amenities is at guests’ own risk. Children must be supervised at all times near the water and pool. There is no lifeguard or on-site supervision. No diving or jumping from the pier. Guests must use all equipment safely, inspect equipment before use, and report any damage or unsafe conditions. Use of the dock, kayaks, and paddleboards requires agreement to a separate waterfront/recreational equipment addendum before arrival.

Stunning Waterfront Retreat w/Pool, Private Dock & Sauna Near Downtown Annapolis

Annapolis, Maryland, United States

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