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

Annapolis Rentals

From $357 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 $357 per night (USD)
VRBO
From $801 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 $801 per night (USD)
Expedia
From $441 per night (USD)
VRBO
Historic 3 Bedroom Downtown Annapolis Townhome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Be close to everything when you stay at this centrally-located, historic townhome! Located steps from the Naval Academy, ...
From $441 per night (USD)
VRBO
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 $141 per night (USD)
VRBO
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $141 per night (USD)
VRBO
From $604 per night (USD)
Expedia
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 $604 per night (USD)
Expedia
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VRBO
Hyde Park Hideaway
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Cute house at the end of a cul-de-sac in a friendly neighborhood! The house has two bedrooms and two full baths. It can ...
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VRBO
From $621 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 $621 per night (USD)
Expedia
From $556 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 $556 per night (USD)
VRBO
From $656 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 $656 per night (USD)
Expedia
From $923 per night (USD)
VRBO
Luxe Houseboat: Breathtaking Skyline 360 Views
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
| OVERVIEW | Welcome to FLOHOM 1 | Bay Escape, your home away from shore! Our luxury houseboat is docked at the premie ...
From $923 per night (USD)
VRBO
From $1173 per night (USD)
Expedia
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Summary: NB: The pool is fully functional however, the hot tub and pool heater will remain out of service until mid Sept ...
From $1173 per night (USD)
Expedia
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VRBO
Charming Annapolis home in Eastport, Now available Commissioning Week!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This delightful restored home is just 3 blocks away from the Eastport Bridge and 1.3 miles away from the Naval Academy ...
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VRBO
From $967 per night (USD)
VRBO
Hidden Treasure on Weems Creek
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
STR00704 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $967 per night (USD)
VRBO
From $1077 per night (USD)
VRBO
Historic Annapolis With Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Historic home with off-street parking for three cars and three blocks from the USNA. Across the Street from St. John Co ...
From $1077 per night (USD)
VRBO
From $865 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 $865 per night (USD)
Expedia
From $1264 per night (USD)
VRBO
Beautiful colonial only 3 miles to the Naval Academy!
Bedrooms:
2
Bathrooms:
6
Sleeps:
11
Beautiful colonial perfect for Naval Academy commissioning week! Bedrooms 6 - Baths: 2.5 Sleeps 11 comfortably. Finish ...
From $1264 per night (USD)
VRBO
From $735 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 $735 per night (USD)
VRBO
From $598 per night (USD)
VRBO
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 $598 per night (USD)
VRBO
From $340 per night (USD)
Expedia
Belle By The Bay Summ
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Summary: This lovely home has 3 bedrooms, 2.5 bathrooms, fully equipped kitchen with large island that seats 4 and an ou ...
From $340 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 ...
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Expedia
From $735 per night (USD)
VRBO
Get Ready for Blissful Getaway! Short Drive to Chase Lloyd House, Pet-Friendly
Bedrooms:
3
Bathrooms:
6
Sleeps:
15
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $735 per night (USD)
VRBO
From $490 per night (USD)
VRBO
Spacious Good-Value Accommodation! w/ Outdoor Pool, Pet-Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $490 per night (USD)
VRBO
From $250 per night (USD)
VRBO
Enjoy a Hassle-Free Stay! Pet-Friendly, Close to William Paca Garden
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $250 per night (USD)
VRBO
From $360 per night (USD)
Expedia
Eastport Charmer Summ
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Your family will be close to everything when you stay at this charming 2-bedroom cottage nestled in the Eastpor ...
From $360 per night (USD)
Expedia
From $1243 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 $1243 per night (USD)
VRBO
From $329 per night (USD)
Expedia
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 $329 per night (USD)
Expedia
From $483 per night (USD)
VRBO
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 $483 per night (USD)
VRBO
From $412 per night (USD)
Expedia
Charming Charles Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history ...
From $412 per night (USD)
Expedia
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VRBO
Plenty of space for the whole family! Close to Stadium, USNA and Downtown
Bedrooms:
4
Bathrooms:
6
Sleeps:
15
Walking distance to stadium and short distance to campus! Large, open floorplan on main level for entertaining and large ...
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VRBO
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Expedia
Walk Everywhere! Your Ultimate Annapolis Retreat on Horn Point
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Escape to your ideal rental property at 125 Chester Avenue, located in the desirable neighborhood of Horn Point in Annap ...
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Expedia
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VRBO
4 Bed & 3 Bath Contemporary in Heart of Eastport!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
DT Annapolis/ Eastport Contemporary home w open floor plan! Kitchen w large breakfast bar, SS appliances, white cabinetr ...
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VRBO
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Expedia
Contemporary in Heart of Eastport w 2 car garage!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Contemporary home with open floor plan & 2 car detached garage! Kitchen w large breakfast bar, SS appliances, white cabi ...
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Expedia
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VRBO
2003 Craftsman; Heart of Eastport!
Bedrooms:
0
Bathrooms:
0
Sleeps:
0
Eastport Craftsman (2003). Short stroll to DT Historic Annapolis shops & Restaurants! Open floor plan! Stunning 2,464 sq ...
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VRBO
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Expedia
Heart of Eastport 4 bedroom Modern Craftsman!
Bedrooms:
0
Bathrooms:
0
Sleeps:
0
Stunning 3,600 sq ft 4 bed/ 3 1/2 bath Contemporary Eastport Craftsman (2003). Short scenic stroll to DT Historic Annapo ...
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Expedia
From $341 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 $341 per night (USD)
VRBO
$Restful and Charming Home in Eastport\n$
From $393 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 $393 per night (USD)
Expedia
From $692 per night (USD)
VRBO
The Crabby Patty Summ
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Summary: Nestled in the heart of historic downtown Annapolis, this three-bedroom home offers a perfect blend of modern c ...
From $692 per night (USD)
VRBO
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Expedia
Beautiful Victorian in Great Eastport Location
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Available for Annapolis Boat Shows. Large historic Victorian in desirable Eastport, close to restaurants and short walk ...
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Expedia
From $711 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 $711 per night (USD)
VRBO
From $807 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 $807 per night (USD)
Expedia
From $357 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 $357 per night (USD)
VRBO
From $444 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 $444 per night (USD)
Expedia
From $495 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 $495 per night (USD)
VRBO
From $948 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 $948 per night (USD)
Expedia
From $535 per night (USD)
VRBO
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Anchors Away Abode Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $535 per night (USD)
VRBO
From $573 per night (USD)
Expedia
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 $573 per night (USD)
Expedia
From $582 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 $582 per night (USD)
VRBO
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Expedia
WALK TO DOWNTOWN ANNAPOLIS, EGO ALLEY, NAVAL STADIUM & ACADEMY
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This home was newly renovated in 2021 and is located in the highly desirable Murray Hill Neighborhood. Conveniently loc ...
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Expedia
From $319 per night (USD)
VRBO
Annapolis Escape, Steps to Harbor backs to Gate 1
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This ground floor, private entrance condo has been fully renovated w/ new paint, floors, bath & kitchen. Queen Bed & sle ...
From $319 per night (USD)
VRBO
From $855 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 $855 per night (USD)
VRBO
From $1162 per night (USD)
VRBO
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 $1162 per night (USD)
VRBO
From $467 per night (USD)
Expedia
Gorgeous & bright retreat with patio, firepit, W/D, & stunning rooftop views
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Skyline Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $467 per night (USD)
Expedia
From $296 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 $296 per night (USD)
VRBO
From $571 per night (USD)
Expedia
Cute bungalow blocks to Stadium
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: This stylish two bedroom home is conveniently located in Annapolis' Germantown neighborhood off West Street, ne ...
From $571 per night (USD)
Expedia
From $1535 per night (USD)
VRBO
Stately Brick Ranch On Corner Lot with Private Backyard for Entertaining
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
STR00803 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1535 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 $721 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 $721 per night (USD)
VRBO
From $570 per night (USD)
Expedia
Annapolis House Minutes from Downtown
Bedrooms:
2
Bathrooms:
4
Sleeps:
13
This Quiet peaceful location with Spacious 4 bedroom, 2 full and 1 half bath is just 3 miles from Downtown Annapolis. Pe ...
From $570 per night (USD)
Expedia
From $841 per night (USD)
VRBO
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 $841 per night (USD)
VRBO
From $933 per night (USD)
Expedia
USNA Luxury Home, parking, pet friendly
Bedrooms:
2
Bathrooms:
5
Sleeps:
13
Steps to the academy and downtown. 1 parking spot included for guests in a garage just steps from our home in the Hillm ...
From $933 per night (USD)
Expedia
From $652 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 $652 per night (USD)
VRBO
From $542 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 $542 per night (USD)
VRBO
From $668 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 $668 per night (USD)
VRBO
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Expedia
Annapolis Charmer! 2BR Bright BSMT APT 3 mi to DT
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
About this space Quiet, cozy established single family neighborhood with a huge yard. Take in the history/music scene a ...
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Expedia
From $299 per night (USD)
VRBO
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 $299 per night (USD)
VRBO
From $468 per night (USD)
Expedia
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 $468 per night (USD)
Expedia
From $293 per night (USD)
VRBO
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 $293 per night (USD)
VRBO
From $1325 per night (USD)
Expedia
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 $1325 per night (USD)
Expedia
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VRBO
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 ...
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VRBO
From $1102 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 $1102 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 $240 per night (USD)
Expedia
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 $240 per night (USD)
Expedia
From $306 per night (USD)
VRBO
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 $306 per night (USD)
VRBO
From $1139 per night (USD)
Expedia
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 $1139 per night (USD)
Expedia
Click For Pricing
VRBO
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 ...
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VRBO
From $1338 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 $1338 per night (USD)
VRBO
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VRBO
Water-view condo with rooftop pool & balcony - minutes from downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
USNA Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
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VRBO
From $284 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 $284 per night (USD)
Expedia
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VRBO
Downtown Annapolis Luxury House
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Our downtown luxury cottage is located 1.4 miles from Church Circle, which is the heart of downtown Annapolis. We are wa ...
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VRBO
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Expedia
Beautifully Furnished Home, Steps to USNA Stadium, Walk to Downtown Annapolis!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This 3 BR/3 Bath home is literally steps from the USNA Stadium (graduation) and within walking distance of downtown Anna ...
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Expedia
From $1419 per night (USD)
VRBO
Upscale home in Eastport / Annapolis
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Ideal location in the heart of Eastport, walking distance to everything Annapolis offers. Only 3 blocks to the Spa Creek ...
From $1419 per night (USD)
VRBO
From $717 per night (USD)
Expedia
Charming 3-bedroom house with AC and WiFi in enchanting Annapolis/Eastport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Stay comfortably in Annapolis at this 3-bedroom house. With 1 king bed, 1 queen bed, and 1 full bed, this tremendous pro ...
From $717 per night (USD)
Expedia
From $475 per night (USD)
VRBO
Waterfront 2-Bedroom Condo on Spa Creek
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to your home away from home in Annapolis! Nestled in the charming neighborhood of Eastport, this beautifully app ...
From $475 per night (USD)
VRBO
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Expedia
Anchor Drop
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Beautiful modern single-family home with heated pool. Located in Eastport, Annapolis, Maryland. Totally renovated in 2 ...
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Expedia
From $550 per night (USD)
VRBO
Ahoy! Game Room, Screened Porch, Yard Mins to DTA
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Welcome to The Buccaneer, a family-friendly home located just 3 miles from Historic Downtown Annapolis and Eastport. Thi ...
From $550 per night (USD)
VRBO
From $3136 per night (USD)
VRBO
Stunning remodel in Murray Hill
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to 9th wing (USNA reference for the boat schoolers out there!) We just completed renovations on this spacious h ...
From $3136 per night (USD)
VRBO
From $647 per night (USD)
VRBO
Darling 2 BR home with parking in the sought after Murray Hill section of Historic Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR22-145187 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $647 per night (USD)
VRBO
From $869 per night (USD)
Expedia
Brand New Spacious Luxury Home
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
This brand-new build luxury home in Eastport close to downtown Annapolis has everything you and your guests (up to 16 to ...
From $869 per night (USD)
Expedia
From $149 per night (USD)
VRBO
Minutes from History: Room w/ Free Breakfast Near Downtown Annapolis
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $149 per night (USD)
VRBO
From $167 per night (USD)
VRBO
Our Welcoming Suite in Annapolis Near Historic Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $167 per night (USD)
VRBO
From $151 per night (USD)
VRBO
Annapolis Adventure: Room w/ Outdoor Pool + Easy Access to Historic Sites
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $151 per night (USD)
VRBO
From $520 per night (USD)
Expedia
Stylish & New, Pet Friendly Fenced Yard, Walkable Downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This stunning detached home, designed by Stylish Stays, is the perfect place for a stay in THE HEART of Annapolis. This ...
From $520 per night (USD)
Expedia
From $576 per night (USD)
VRBO
Dog friendly! Next to Navy Stadium and DTA Shuttle!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Enjoy your stay in our charming home centrally located directly across from Navy-Marine Corps Memorial Stadium on Taylor ...
From $576 per night (USD)
VRBO
$Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n$
From $318 per night (USD)
Expedia
Vintage Retreat: 5 minute walk to downtown, Naval Academy, Stadium and more.\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Immerse yourself in the rich history of Annapolis at our century-old home in Presidents Hill. With 3 bedrooms, 2 baths, ...
From $318 per night (USD)
Expedia
From $393 per night (USD)
VRBO
Downtown Pinkney House w/Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: The Pinkney house is a 2 bedroom, 2.5 bath town home boasts an unparalleled location within close proximity to ...
From $393 per night (USD)
VRBO
From $560 per night (USD)
Expedia
Historic Annapolis Home!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
🌟 Discover the Allure of Historic Annapolis Living! 🌟 Welcome to your captivating 2-bedroom, 1.5-bath home nestled in ...
From $560 per night (USD)
Expedia
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VRBO
Murray Hill beauty with short walk to Main Street
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
A perfect place to celebrate your Midshipmen's commissioning in a 1900 built home! Fabulous patio and back yard to enjo ...
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VRBO
From $182 per night (USD)
VRBO
Maryland Inn 2 Double Beds, Historic Inns, Modern Amenities, Event Space, City Center
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Steps from the State House & Naval Academy, explore city attractions, historic waterfront, Main Street shops, and dine a ...
From $182 per night (USD)
VRBO

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