Annapolis, Maryland Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Annapolis, Maryland on RentalSaver.com!

Annapolis Rentals

From $299 per night (USD)
VRBO
Downtown furnished apartment - walking distance to restaurants
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Church owned 2nd Floor apartment in historic house - fully furnished - eat-in kitchen, dining room and living room - has ...
From $299 per night (USD)
VRBO
From $473 per night (USD)
Expedia
Go Navy! Steps to USNA, City Dock & Street Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Stay in the heart of Historic Annapolis just steps from the waterfront, shops, restaurants, and the Naval Academy. Owned ...
From $473 per night (USD)
Expedia
From $683 per night (USD)
VRBO
Private Patio at Charming Hanover House Across from USNA Gate 3
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a ...
From $683 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Bay View Studio Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $314 per night (USD)
Expedia
From $1165 per night (USD)
VRBO
Quiet home with large yard, close to Navy Bridge.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Come relax at our spacious home and enjoy our quiet neighborhood! We are located near the greatest attractions in Annapo ...
From $1165 per night (USD)
VRBO
From $418 per night (USD)
Expedia
Easy Annapolis lodging - still available for Sailboat Show!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This home (divided/upper floor only) is perfect for families, situated on a quiet residential street with a gorgeous bac ...
From $418 per night (USD)
Expedia
From $384 per night (USD)
VRBO
ACROSS FROM STADIUM - walk to downtown Annapolis.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Across the street from the Navy and Marine Corps Stadium and walking distance to historic downtown Annapolis - you will ...
From $384 per night (USD)
VRBO
From $1011 per night (USD)
Expedia
Serene Sunsets at Historic Waterfront Home
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sit ...
From $1011 per night (USD)
Expedia
From $442 per night (USD)
VRBO
Gem in Downtown Annapolis, close to USNA, St. John's College
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Comfortable stay on quiet street close to Gate 3 USNA and St. John's College. Quick walk to Maryland State House, Maryla ...
From $442 per night (USD)
VRBO
From $651 per night (USD)
Expedia
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Harrison Hall Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $651 per night (USD)
Expedia
From $1007 per night (USD)
VRBO
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Welcome to Modern Elegance in Historic Annapolis Step into this fully-renovated 1900s home, where modern sophistication ...
From $1007 per night (USD)
VRBO
From $498 per night (USD)
Expedia
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
421 Irie City Of Annapolis License Number 145052 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! ...
From $498 per night (USD)
Expedia
From $1605 per night (USD)
VRBO
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
The Admiral's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1605 per night (USD)
VRBO
From $1518 per night (USD)
Expedia
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
The Master Shipwright Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1518 per night (USD)
Expedia
From $449 per night (USD)
VRBO
Stunning Waterfront Cottage with Breathtaking Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in t ...
From $449 per night (USD)
VRBO
From $518 per night (USD)
VRBO
Large Luxury Apartment In Downtown Annapolis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
2 Bed/2 Bath Apartment with additional family room with brand new queen sleeper sofa in Historic Downtown Annapolis step ...
From $518 per night (USD)
VRBO
From $753 per night (USD)
VRBO
Waterfront Oasis in Eastport-Easy Walk to Downtown
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. With 4 bedrooms and an open studio spac ...
From $753 per night (USD)
VRBO
From $328 per night (USD)
VRBO
Walk everywhere . . .just minutes to historic Annapolis, Updated.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A modern historic gem in a 10 unit building in Eastport or as the locals call it the Maritime Republic of Eastport or "M ...
From $328 per night (USD)
VRBO
From $527 per night (USD)
VRBO
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to your dream stay nestled in the heart of Historic Downtown Annapolis! Located just 45 feet from downtown Anna ...
From $527 per night (USD)
VRBO
From $195 per night (USD)
Expedia
Beautiful Condo - Water View Near City Dock
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Check out our winter rates for January, February and March! The Newport Condominium has a beautiful water view of Spa ...
From $195 per night (USD)
Expedia
From $689 per night (USD)
VRBO
Jackson's Bunker in Eastport with fenced-in backyard and dog friendly
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
Located in the Annapolis "Republic of Eastport", this charming pet-friendly home is a short walk to restaurants, shops, ...
From $689 per night (USD)
VRBO
From $855 per night (USD)
VRBO
Charming 239-year-old former tavern 1 block to water & shops
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
239-year-old home, formerly a tavern & inn where Thomas Jefferson bought salt & stockings. Beautifully furnished with an ...
From $855 per night (USD)
VRBO
From $254 per night (USD)
VRBO
Pristine Downtown 1-Bedroom Steps from State House
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy your stay in the heart of Annapolis's historic district, steps away from the Maryland State House and a few minute ...
From $254 per night (USD)
VRBO
From $471 per night (USD)
VRBO
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Chesapeake Bay awaits you at this Annapolis vacation rental! 'Admiral's Post' is situated under 4 miles from the cit ...
From $471 per night (USD)
VRBO
From $735 per night (USD)
VRBO
USNA Home Steps to Stadium Dog-Friendly w Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
In Navy jargon, the goat locker is a lounge, sleeping area, and galley on board a naval vessel which is reserved for the ...
From $735 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Cozy Home in Beautiful Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Keep it simple at this peaceful and centrally located Annapolis home. It has all the amenities and essentials of a home ...
From $182 per night (USD)
Expedia
From $1531 per night (USD)
VRBO
Annapolis Bayfront Home
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Beautifully restored turn of the century beach cottage located on an acre of landscaped property with magnificent views ...
From $1531 per night (USD)
VRBO
Click For Pricing
Expedia
Hideaway in the middle of everything
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Clean, spacious Eastport cottage in a prime location to downtown Annapolis and the United States Naval Academy. Both are ...
Click For Pricing
Expedia
From $668 per night (USD)
VRBO
Multiple Gathering Spaces, Private Backyard & Free Parking at Townhome 1 Block to Capital Bldg
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Naptown Nook, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in th ...
From $668 per night (USD)
VRBO
From $1040 per night (USD)
Expedia
MODERN 2022 NEWLY BUILT TOWNHOME
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two li ...
From $1040 per night (USD)
Expedia
From $215 per night (USD)
VRBO
Waterfront Condo- Eastport Annapolis- Next to Spa Creek Draw Bridge & AYC
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Upscale renovated units on the first floor of Yacht Club Condos. Both units A1 and C1 are available. First floor walk o ...
From $215 per night (USD)
VRBO
From $540 per night (USD)
Expedia
7 mins away from Downtown Annapolis
Bedrooms:
2
Bathrooms:
6
Sleeps:
11
Come stay at our cozy house. Perfect for a group of 11people. Share beautiful memories that will last a lifetime. Close ...
From $540 per night (USD)
Expedia
From $543 per night (USD)
VRBO
Escape Villa in Downtown Annapolis
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Do ...
From $543 per night (USD)
VRBO
From $1088 per night (USD)
Expedia
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
The location is ideal - one short block to USNA Gate 3, and just 4 blocks to the downtown waterfront. Home has a privat ...
From $1088 per night (USD)
Expedia
Click For Pricing
VRBO
NEW lovely studio apartment with onsite parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy a stylish experience at this centrally-located place! (Two guests maximum) The space null. Other things to note Pl ...
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VRBO
Click For Pricing
Expedia
Charming Eastport
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Who needs a boat to stay at a marina? Eastport Yacht Center has a quaint one bedroom apartment located in charming Eastp ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Condo Houseboat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This BRAND NEW condo house boat is nestled in Back Creek. The views of the Chesapeake Bay are amazing! This is the best ...
Click For Pricing
VRBO
From $458 per night (USD)
Expedia
Chesapeake Comfort, Annapolis.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Annapolis Bungalow Home that is professionally cleaned and is a full time short-term rental. I have been a Superhost wit ...
From $458 per night (USD)
Expedia
From $2018 per night (USD)
VRBO
Upscale multi-level retro home with large deck, washer/dryer, and lovely patio
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
St Johns Adjacent Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $2018 per night (USD)
VRBO
From $2726 per night (USD)
Expedia
3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Ensign's Ridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $2726 per night (USD)
Expedia
From $768 per night (USD)
VRBO
Annapolis 4 BR w/ Gameroom & fire pits-walk everywhere!
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
This is the perfect house for your family friendly visit to Annapolis, MD Enjoy everything the sought after Eastport ne ...
From $768 per night (USD)
VRBO
Click For Pricing
Expedia
Coastal Cabins.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Charming & cozy, 2- level Victorian style home built in the 1920s. Well stocked w/ modern conveniences for your home awa ...
Click For Pricing
Expedia
From $689 per night (USD)
VRBO
Private yard and screened porch at Historic happy home, steps to Main Street with parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic ...
From $689 per night (USD)
VRBO
Click For Pricing
Expedia
USNA Commissioning Week - 2 Blocks Away
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Host the perfect USNA Commissioning week family get together - just two blocks from the Naval Academy! Modern convenienc ...
Click For Pricing
Expedia
From $331 per night (USD)
VRBO
Perfect Eastport Location, walk everywhere, Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Leave your car behind and walk to everything Annapolis, Eastport is full of charm, Restaurants, Museums, live music. Com ...
From $331 per night (USD)
VRBO
From $937 per night (USD)
Expedia
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Be ...
From $937 per night (USD)
Expedia
From $986 per night (USD)
VRBO
Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
Bedrooms:
4
Bathrooms:
6
Sleeps:
18
*** Commissioning Wk 2024 AVAILABLE*** Unique opportunity to rent an entire triplex Downtown Annapolis! One property wi ...
From $986 per night (USD)
VRBO
From $809 per night (USD)
VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
From $809 per night (USD)
VRBO
From $896 per night (USD)
VRBO
BAY RIDGE MODERN HOME WITH VINTAGE CHARM
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Beautiful spacious modern family home with vintage charm. A great gathering spot for family or just wanting to spend som ...
From $896 per night (USD)
VRBO
From $606 per night (USD)
VRBO
3 bdrm close to city center, great yard & parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Approx .7 mile to stadium, 1.4 to Naval Academy. Walk to free shuttle at Park Place and to great coffee every morning fr ...
From $606 per night (USD)
VRBO
From $347 per night (USD)
VRBO
18th Cent. Charm in Historic Downtown Annapolis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Lower level furnished apartment, in one of Historic Annapolis's 10 oldest Private residences. Lovely wood, brick & ornam ...
From $347 per night (USD)
VRBO
From $684 per night (USD)
Expedia
Secluded Cozy Cottage in Historic Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Beautifully restored 1930s cottage w/ open floor plan & vaulted ceilings provide a homey vibe Enjoy having Historic Ann ...
From $684 per night (USD)
Expedia
From $1261 per night (USD)
VRBO
Waterfront Architectural Masterpiece with private dockage available.
Bedrooms:
4
Bathrooms:
5
Sleeps:
11
Heron Point House is an owner imagined home, designed by one of the region's leading architects and built to perfection. ...
From $1261 per night (USD)
VRBO
From $127 per night (USD)
VRBO
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Modern family units with private kitchens for the ultimate Annapolis experience This listing is for a room within a hot ...
From $127 per night (USD)
VRBO
From $566 per night (USD)
VRBO
Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private deck and backyard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to this mid-century modern, Cape Cod in West Annapolis. This "Ralph-Lauren Cottage" exudes that "Annapolitan fee ...
From $566 per night (USD)
VRBO
From $584 per night (USD)
Expedia
Location is perfect and a big bonus we have our own parking at the home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Our favorite part about this home is its location in DTA with parking. We can walk to all the restaurants, pubs, USNA, ...
From $584 per night (USD)
Expedia
From $514 per night (USD)
VRBO
Waterfront Condo with Rooftop Pool, Spa Creek Views & Prime Eastport Location with Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Waterfront Condo with Spa Creek Views, Rooftop Pool & Prime Eastport Location Experience Annapolis from this beautifull ...
From $514 per night (USD)
VRBO
From $595 per night (USD)
Expedia
History & Charm Are Only Steps from Main Street and City Dock at Catch 22
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
This charming 3-BR, 2.5-BA townhome is just a 1/2-block from the city dock and is a luxurious vacation getaway in the he ...
From $595 per night (USD)
Expedia
From $1011 per night (USD)
VRBO
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Summary: This is a gorgeous home with in ground *heated* "6 month" pool & "9 month" hot tub - less than a mile walk from ...
From $1011 per night (USD)
VRBO
From $614 per night (USD)
Expedia
Dog-friendly house with yard, deck, firepit, washer/dryer & AC - near golf
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Seas The Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $614 per night (USD)
Expedia
From $781 per night (USD)
VRBO
Annapolis gem with beautiful outdoor dining! Near U.S. Naval Academy
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
In Annapolis this charming 3-bedroom home is moments away from USNA Stadium, and the Naval Academy, and picturesque Cit ...
From $781 per night (USD)
VRBO
From $434 per night (USD)
Expedia
Historic district home, View of the Capital, WALK Downtown, w/ Outdoor Dining!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Newly renovated w ...
From $434 per night (USD)
Expedia
From $674 per night (USD)
VRBO
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautifully renovated home in the heart of West Annapolis. The main level has been updated to an open floor plan to acco ...
From $674 per night (USD)
VRBO
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Expedia
Lakefront House- near downtown Annapolis
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Great place to relax and enjoy the serene view of the lake in this spacious house with multiple balconies. Enjoy a hotel ...
Click For Pricing
Expedia
From $189 per night (USD)
VRBO
Enjoy a Hassle-Free Stay! Pet-Friendly, Close to William Paca Garden
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Modern family units with private kitchens for the ultimate Annapolis experience This listing is for a room within a hot ...
From $189 per night (USD)
VRBO
From $1304 per night (USD)
VRBO
Luxury Waterfront Annapolis home with your very own Private Beach & Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
About this space Stunning Contemporary Home with private beach! House has been listed on another site receiving five st ...
From $1304 per night (USD)
VRBO
From $326 per night (USD)
VRBO
Historic Home with Parking Steps From Capital & USNA
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to this vibrant downtown Annapolis oasis—a unique purple parallelogram with a parking spot. From the front door, ...
From $326 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Charming West Annapolis Cottage home
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: This two-bedroom home in West Annapolis is a charming residence that boasts a spacious back yard, providing amp ...
From $409 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium
Bedrooms:
1
Bathrooms:
4
Sleeps:
7
Welcome to this Annapolis gem located in the historic city of Annapolis. Enjoy living walking distance from all of the b ...
From $317 per night (USD)
VRBO
$Restful and Charming Home in Eastport\n$
From $384 per night (USD)
Expedia
Restful and Charming Home in Eastport\n
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
We offer a 10% military discount upon request! A cozy home away from home in Eastport located within 1.5 Miles of Histor ...
From $384 per night (USD)
Expedia
From $579 per night (USD)
VRBO
Historic downtown townhome with brick courtyard, sunroom & parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Corner Courtyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $579 per night (USD)
VRBO
From $779 per night (USD)
Expedia
Walk to Navy Stadium, Restaurants, Shops from Luxury Home with Private Backyard, Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to Your Luxury West Annapolis Retreat! Nestled in the heart of West Annapolis, this beautifully remodeled crafts ...
From $779 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Welcome to my home! I hope that you love it as much as I do. It is an open concept 3 bedroom (two queens and a king) 1 ...
From $344 per night (USD)
VRBO
From $438 per night (USD)
Expedia
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Corner House – Quaint and Cozy 2 Bedroom Suite with Parking The Corner House is a hidden gem located in the quaint P ...
From $438 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Your family will be close to everything when you stay at this centrally-located place. Two blocks to Main Street, the Na ...
From $482 per night (USD)
VRBO
From $940 per night (USD)
Expedia
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Located on one of the most coveted streets in downtown Annapolis, walk to Main St. and City Dock. The Thomas Hyde House ...
From $940 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Annapolis Retreat - 7 mins from downtown Annapolis!
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Welcome to this charming five-bedroom, two-bathroom escape nestled in the Hillsmere Shores neighborhood of Annapolis. Ju ...
From $420 per night (USD)
VRBO
From $568 per night (USD)
VRBO
Annapolis Downtown - Historic Home - Brand New Furnishings. Walk to attractions
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We’re a Navy + Army Family with deep ties to the Naval Academy (and West Point…sorry, Navy fans). We love Annapolis and ...
From $568 per night (USD)
VRBO
From $779 per night (USD)
VRBO
Spacious Annapolis Abode: 507 Schley Rd Vacation Rental, Minutes from Downtown!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
This lovely 4-bedroom home boasts 3 full bathrooms and room to comfortably sleep up to 12 people. With its spacious and ...
From $779 per night (USD)
VRBO
From $1070 per night (USD)
Expedia
Historic Annapolis Charmer <1Mile to NMC Stadium
Bedrooms:
4
Bathrooms:
6
Sleeps:
20
IMMACULATE SPACE AND RARE FIND IN DOWNTOWN ANNAPOLIS SLEEPING UP TO 12! Beautifully maintained 1930's home in the middl ...
From $1070 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Home Away From Home S
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Conveniently located to restaurants, shopping and other fun activities in the area. This is an ideal rental for ...
From $349 per night (USD)
VRBO
From $1583 per night (USD)
VRBO
Marvelous Home with Backyard Living Room in Murray Hill
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
NBS23-145336 Welcome to our charming vacation rental house nestled in the picturesque Murray Hill neighborhood of Annapo ...
From $1583 per night (USD)
VRBO
From $651 per night (USD)
VRBO
Eastport Oasis 4 BR 2 BA fully renovated home on quiet street with parking and gorgeous outdoor space
Bedrooms:
2
Bathrooms:
5
Sleeps:
8
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $651 per night (USD)
VRBO
From $695 per night (USD)
Expedia
Fisher House: Steps From USNA + Covered Parking!
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Summary: Welcome to our beautifully renovated historic home in the heart of Annapolis! The Fisher House, built in 1885, ...
From $695 per night (USD)
Expedia
From $626 per night (USD)
VRBO
Restriction Retreat - Relax & walk to Main St
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an u ...
From $626 per night (USD)
VRBO
From $531 per night (USD)
VRBO
Coastal Chesapeake cottage in Eastport
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Welcome to our newest listing - The Coastal Cottage on Chesapeake located in the Maritime community of Eastport . This b ...
From $531 per night (USD)
VRBO
From $909 per night (USD)
VRBO
Steps to USNA with Large Private Patio & Free Off-Site Parking
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Stay in this restored historic Annapolis home, located just steps from both USNA Gates 1 and 3. The proud Navy graduate ...
From $909 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Bay Ridge house by Quiet Waters Park, Thomas Point Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Brand new home with comfortable beds, open floor plan with kitchen excellent for entertaining, and fully equipped. All f ...
From $278 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Luxury Gourmet Kitchen with Backyard and Parking at 1st floor Eastport Apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This beautifully upgraded one-bedroom apartment on the 1st floor of a two-flat is just steps from local popular restaura ...
From $469 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Property is 2 bedrooms and 1 bathroom furnished with brand new furniture. Bedrooms have fitted with comfortable queen si ...
From $278 per night (USD)
Expedia
From $1240 per night (USD)
VRBO
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Bedrooms:
4
Bathrooms:
6
Sleeps:
16
The Oaks Inn is an exceptional well-kept home, nestled in the heart of Historic Downtown Annapolis, that seamlessly comb ...
From $1240 per night (USD)
VRBO
Click For Pricing
Expedia
Stunning Waterfront Home with Incredible Views
Bedrooms:
5
Bathrooms:
5
Sleeps:
15
Perfect home for a family getaway, Commissioning Week or Boat Show event. Room for all to sleep, gather and play in thi ...
Click For Pricing
Expedia
From $1099 per night (USD)
VRBO
New home in historic Eastport! Steps from restaurants, retail, and more.
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Virtual tour: https://cquh.short.gy/eastportretreat Welcome to our charming Eastport retreat in Annapolis, Maryland – w ...
From $1099 per night (USD)
VRBO
From $174 per night (USD)
VRBO
2 BR home on quiet street in Eastport with lovely screened porch.
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
RENT-004550-2024 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE B ...
From $174 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Summer Special in Annapolis! Pristine, Peaceful, Walkable 1B/1B Apt. Sleeps 4.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Fox Haven, a bright, pristine 1 Bed/1 Bath apartment that sleeps 3-4 adults comfortably and has its own separ ...
From $238 per night (USD)
VRBO
From $482 per night (USD)
Expedia
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover this delightful three-bedroom getaway nestled within the ancient Annapolis historical area! Nestled just a 17-m ...
From $482 per night (USD)
Expedia
From $1141 per night (USD)
VRBO
Stunning Craftsman Steps to Downtown Annapolis & Spa Creek with Game Room, Parking and Backyard
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Walk to Everything Ideal for Families & Groups Welcome to your Eastport escape! Stay in this stunning, professionally d ...
From $1141 per night (USD)
VRBO
Click For Pricing
Expedia
Large House Downtown Annapolis with 2 Hot Tubs and 4 parking places
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
This Navy Themed house is located jn downtown annapolis, walking distance to all the shops and restaurants in annapolis ...
Click For Pricing
Expedia
From $1364 per night (USD)
VRBO
Fabulous Waterfront Contemporary with Rooftop Hot Tub!
Bedrooms:
3
Bathrooms:
5
Sleeps:
15
RENT-000856-2025 THIS PROPERTY IS MANAGED BY ANNAPOLIS ACOCMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM M ...
From $1364 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Newly Updated EV Charger Ready Peaceful Home in Annapolis
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Welcome to our stylish and modern home, where comfort meets convenience! Here's what you can expect during your stay: ✔ ...
From $251 per night (USD)
Expedia

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