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

Annapolis Rentals

From $398 per night (USD)
VRBO
NEW Eastport Bungalow walkable to USNA, Restaurants, & Historic Annapolis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Your family will be 1mi. to Main Street & Downtown Annapolis home of the US Naval Academy (ask about our Navy family di ...
From $398 per night (USD)
VRBO
From $1565 per night (USD)
Expedia
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Bedrooms:
5
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 $1565 per night (USD)
Expedia
From $1011 per night (USD)
VRBO
2 BR home on quiet street in Eastport with lovely screened porch.
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
RENT-004550-2024 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE B ...
From $1011 per night (USD)
VRBO
$Summer Special in Annapolis! Pristine, Peaceful, Walkable 1B\/1B Apt. Sleeps 4.$
From $273 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 $273 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Book for CW 2025 Gourmet kitchen with backyard and parking at 1st floor Eastport apartment
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Still available for Commissioning Week 2025! This beautifully upgraded one-bedroom apartment on the 1st floor of a two- ...
From $448 per night (USD)
VRBO
From $641 per night (USD)
Expedia
Fisher House - Downtown Annapolis!
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Summary: Welcome to our beautifully renovated historic home in the heart of Annapolis! The Fisher House, built in 1885, ...
From $641 per night (USD)
Expedia
From $1035 per night (USD)
VRBO
USNA Luxury Home, parking, pet friendly
Bedrooms:
3
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 $1035 per night (USD)
VRBO
From $296 per night (USD)
Expedia
Home Away From Home S
Bedrooms:
2
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)
Expedia
From $699 per night (USD)
VRBO
Cozy Annapolis Abode: 507 Schley Rd Vacation Rental, Minutes from Downtown!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Property Highlights: This lovely 4-bedroom home boasts 3 full bathrooms and room to comfortably sleep up to 12 people. ...
From $699 per night (USD)
VRBO
$Gorgeous dog-friendly retreat w\/ fireplace, patio, & firepit$
From $505 per night (USD)
Expedia
Gorgeous dog-friendly retreat w\/ fireplace, patio, & firepit
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Anchors Away Abode Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $505 per night (USD)
Expedia
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VRBO
Downtown Annapolis Park
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Two bedroom and two bathroom in Historic Annapolis, only 1 mile from arts district (west street), 2 miles from downtown ...
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VRBO
From $439 per night (USD)
Expedia
Historic Downtown House with Off Street Parking
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Spacious living with all the modern amenities. Prime location - 1 block from the water, restaurants, and shops. Park you ...
From $439 per night (USD)
Expedia
$Historic & sunny home w\/ Fireplace steps from USNA & Downtown Annapolis$
From $497 per night (USD)
VRBO
Historic & sunny home w\/ Fireplace steps from USNA & Downtown Annapolis
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This beautiful 3-bedroom, 2.5 bath home built in 1900 is located on Prince George Street, one block from Annapolis City ...
From $497 per night (USD)
VRBO
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Expedia
Indoor Soft Hot Tub - Family Stay @ The Cape!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Make some memories at this unique and family-friendly place. Family Friendly Staycation fully outfitted to accommodate ...
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Expedia
From $382 per night (USD)
VRBO
Historic Annapolis Home 1.5 blocks from center of town.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Historic home 1.5 blocks from center of town. Easy walk to the shops, food, harbor, Naval Academy and historic attractio ...
From $382 per night (USD)
VRBO
From $1184 per night (USD)
Expedia
West Annapolis Cottage
Bedrooms:
5
Bathrooms:
7
Sleeps:
14
Summary: Recently renovated, this is the perfect location for your family & friends to enjoy Naval Academy events, boat ...
From $1184 per night (USD)
Expedia
From $326 per night (USD)
VRBO
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Located in the heart of Annapolis' historic district sits this one bedroom, 1.5 bath cozy apartment. A mere stone's thr ...
From $326 per night (USD)
VRBO
From $376 per night (USD)
Expedia
Adorable home steps from Navy Stadium!
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Can’t beat the space and location of this property for your trip to Annapolis! Just a block away from Navy Stadium for a ...
From $376 per night (USD)
Expedia
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VRBO
Historic Annapolis Home, Convenient to Downtown!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
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VRBO
From $1205 per night (USD)
Expedia
Updated historic home with parking; near Academy, college & harbor - central AC
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Anchors Aweigh Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1205 per night (USD)
Expedia
From $261 per night (USD)
VRBO
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Five blocks to Naval Bagels, Agave, Chessie's Wharf, Evelyn's, Bean Rush Cafe, Rutabagas, Grauls Groceries and other sho ...
From $261 per night (USD)
VRBO
From $1201 per night (USD)
Expedia
Newly renovated downtown home with patio, gas grill, and gas fireplace
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Blue Angel's Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1201 per night (USD)
Expedia
From $411 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 $411 per night (USD)
VRBO
From $721 per night (USD)
Expedia
Darling 2 BR home with parking in the sought after Murray Hill section of Historic Annapolis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
STR22-145187 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $721 per night (USD)
Expedia
From $409 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 $409 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 $1413 per night (USD)
VRBO
Downtown Annapolis Duke's House
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
Summary: This newly renovated 4-bedroom, 3.5 bathroom home is perfectly situated in the heart of historic downtown Anna ...
From $1413 per night (USD)
VRBO
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Expedia
Spend Commissioning Week Here: Walk to Yard, Pool, Hot Tub, Kayaks, and more...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Park once and walk everywhere! Plus, enjoy our pool, hot tub, fire pit and large patio for your gatherings. Have your mo ...
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Expedia
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VRBO
Amazing townhome in Annapolis, near Restaurants, USNA, Shopping centers, & more
Bedrooms:
4
Bathrooms:
3
Sleeps:
3
Amazing three bedroom townhome with Masters suite(with full bathroom), and 2 additional bedrooms with access to one full ...
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VRBO
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Expedia
Charming Historic 3-bedroom Estate in Downtown Annapolis
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Welcome to Lynder's Luxury Lodging-Annapolis. Discover this 3-bedroom Colonial gem in the heart of Downtown Annapolis ( ...
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Expedia
From $829 per night (USD)
VRBO
NEW! Cozy Coastal Retreat in the Heart of Annapolis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this charming 3-bedroom, 2-bathroom townhouse, ideally located in the serene community of Eastport in Annapol ...
From $829 per night (USD)
VRBO
From $551 per night (USD)
Expedia
Darling on Dean Street- Nautical home w parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Ideally located between the vibrant West Street and the historic Main Street, our downtown Annapolis home offers easy ac ...
From $551 per night (USD)
Expedia
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VRBO
Efficiency Apartment Close to Annapolis. .
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Furnished efficiency apartment in Annapolis, close to downtown area, and easy access to Highways. Private Entrance, pri ...
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VRBO
From $1100 per night (USD)
Expedia
Historic Annapolis Treasure
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Entire Home in Historic Downtown Annapolis Forget your worries in this spacious and serene enchanting Victorian home in ...
From $1100 per night (USD)
Expedia
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VRBO
Unique 2-Bedroom Condo in Renovated Church Parish House
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Step into a truly exceptional condo nestled in a beautifully preserved historic church, just two blocks from the U.S. Na ...
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VRBO
From $560 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 $560 per night (USD)
Expedia
From $518 per night (USD)
VRBO
Book now for CW 2025 Stay just steps from City Dock at the charming and historic Fleet's Inn
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
Still available for Commissioning Week 2025! Stay in the heart of Historic Annapolis just steps from the waterfront, sh ...
From $518 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Private Annapolis Guest Apartment! Walkable to downtown! Location!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Keep it simple at this peaceful and centrally located guesthouse. This charming guest house w/ private access is located ...
From $334 per night (USD)
Expedia
From $600 per night (USD)
VRBO
Historic Downtown Union House with Free parking & private patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Spectacularly res ...
From $600 per night (USD)
VRBO
From $852 per night (USD)
Expedia
Charming Romantic, or Navy Professional Historic Retreat—Steps to City Dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to our historic home in downtown Annapolis! Enjoy your morning coffee on the front porch and host a BBQ in our ...
From $852 per night (USD)
Expedia
From $686 per night (USD)
VRBO
Steps to USNA and Main St w private patio and parking at Historic gem
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Take a stroll along the brick-lined sidewalks of Prince George Street in the Historic District and to this fully-renovat ...
From $686 per night (USD)
VRBO
From $984 per night (USD)
VRBO
Stunning Annapolis Home! Across from the library, walk to Naval Graduation
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
This 4 BR, 4.5 BA house is perfect for entertaining your guests! Come into our spacious open floor plan. You feel li ...
From $984 per night (USD)
VRBO
From $328 per night (USD)
VRBO
Available for Maryland Legislative Session 2024 ! Perfect location!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy the essence of Historic Annapolis with this recently renovated Maryland Avenue apartment. Located in the 'Johnson ...
From $328 per night (USD)
VRBO
From $349 per night (USD)
Expedia
Prime Viewing for Blue Angels -Rooftop Deck and Water Views of Spa Creek!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
RENT-000642-2025- PLEASE NOTE: IF YOU REQUEST TO BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS ...
From $349 per night (USD)
Expedia
From $568 per night (USD)
VRBO
Steps to Main St at Historic Carriage House in the Heart of Downtown Annapolis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Originally built in 1857, this fully-restored home has a rich history that's been documented from it's original purpose ...
From $568 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Annapolis steps to Harbor and Naval Academy
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Parking included. The heart of Annapolis 1 street from the harbor, fun restaurants & backs to the Naval Academy. This 1s ...
From $382 per night (USD)
Expedia
From $534 per night (USD)
VRBO
Tastefully decorated fully-equipped Eastport Annapolis house with water views
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our renovated 3 story house is located on the peninsula of Eastport, Annapolis. We are across the street from a small m ...
From $534 per night (USD)
VRBO
From $1570 per night (USD)
Expedia
Murray Hill Gem - Your Commissioning Week Home Away from Home
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
NBS22-145072 - PLEASE NOTE: IF YOU BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINALIZE AN ...
From $1570 per night (USD)
Expedia
From $902 per night (USD)
VRBO
Annapolis -Eastport - -3 Bedroom- 3 bath with parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Delightful Arts and Crafts/ Coastal style home. Main Level is open space concept with 9 ft ceilings and plenty of nat ...
From $902 per night (USD)
VRBO
From $590 per night (USD)
Expedia
Cozy 2 BR home with parking and views of the Annapolis Harbor - Walk to everything!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
STR23-145349 - PLEASE NOTE: IF YOU BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS TO FINALIZE AN ...
From $590 per night (USD)
Expedia
From $344 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 $344 per night (USD)
VRBO
From $1455 per night (USD)
Expedia
Historic Annapolis Charmer <1Mile to NMC Stadium
Bedrooms:
5
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 $1455 per night (USD)
Expedia
From $530 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 $530 per night (USD)
VRBO
From $1126 per night (USD)
Expedia
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 $1126 per night (USD)
Expedia
From $1096 per night (USD)
VRBO
Newly-renovated Lighthouse Inn with game room parking, private backyard, walk to downtown
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Stay in this stunning Craftsman home, just steps from the water and everything Eastport/Annapolis has to offer. Enjoy 3 ...
From $1096 per night (USD)
VRBO
From $679 per night (USD)
Expedia
Discover Annapolis charm, just a quick 4-min drive to U.S. Naval Academy
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
In the heart of Annapolis is located this lovely 3-bedroom getaway that's just moments away from the Naval Academy Navy- ...
From $679 per night (USD)
Expedia
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VRBO
Plenty of space for the whole family! Close to Stadium, USNA and Downtown
Bedrooms:
5
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
Beautiful Victorian in Great Eastport Location
Bedrooms:
3
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 $847 per night (USD)
VRBO
Captain's Quarters - Eastport!
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Summary: Escape to this one-of-a-kind, restored 1920s bungalow in Eastport’s sought-after maritime community, perfect fo ...
From $847 per night (USD)
VRBO
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Expedia
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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Expedia
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VRBO
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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VRBO
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Expedia
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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Expedia
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VRBO
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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VRBO
$Downtwn Stylish 3BR\/2BA with Exclusive Parking in Annapolis-USNA Stadium$
From $376 per night (USD)
Expedia
Downtwn Stylish 3BR\/2BA with Exclusive Parking in Annapolis-USNA Stadium
Bedrooms:
2
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 $376 per night (USD)
Expedia
$Restful and Charming Home in Eastport\n$
From $399 per night (USD)
VRBO
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 $399 per night (USD)
VRBO
From $492 per night (USD)
Expedia
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 $492 per night (USD)
Expedia
From $814 per night (USD)
VRBO
USNA-themed dog-friendly home steps from Navy Stadium with parking
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
In Navy jargon, the goat locker is a lounge, sleeping area, and galley on board a naval vessel which is reserved for the ...
From $814 per night (USD)
VRBO
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Expedia
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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Expedia
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VRBO
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 ...
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VRBO
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Expedia
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 ...
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Expedia
From $265 per night (USD)
VRBO
Waterfront Condo- Eastport Annapolis- Next to Spa Creek Draw Bridge & AYC
Bedrooms:
1
Bathrooms:
1
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 $265 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 $701 per night (USD)
VRBO
Escape Villa in Downtown Annapolis
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Do ...
From $701 per night (USD)
VRBO
$Newly renovated townhome with a fenced yard, gas grill, washer\/dryer, central AC$
From $1398 per night (USD)
Expedia
Newly renovated townhome with a fenced yard, gas grill, washer\/dryer, central AC
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
The Herons Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $1398 per night (USD)
Expedia
$Upscale multi-level retro home with large deck, washer\/dryer, and lovely patio$
From $1544 per night (USD)
VRBO
Upscale multi-level retro home with large deck, washer\/dryer, and lovely patio
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
St Johns Adjacent Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1544 per night (USD)
VRBO
From $837 per night (USD)
Expedia
Charming 239-year-old former tavern 1 block to water & shops
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
239-year-old home, formerly a tavern & inn where Thomas Jefferson bought salt & stockings. Beautifully furnished with an ...
From $837 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 $542 per night (USD)
Expedia
Location is perfect and a big bonus we have our own parking at the home!
Bedrooms:
3
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 $542 per night (USD)
Expedia
From $548 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 $548 per night (USD)
VRBO
From $368 per night (USD)
Expedia
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 $368 per night (USD)
Expedia
From $677 per night (USD)
VRBO
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 $677 per night (USD)
VRBO
From $1518 per night (USD)
Expedia
Stately Brick Ranch On Corner Lot with Private Backyard for Entertaining
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
STR00803 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1518 per night (USD)
Expedia
From $688 per night (USD)
VRBO
Stay close to USNA Stadium with screened-in porch and parking
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Welcome to this charming Cape Cod on half an acre right outside downtown Annapolis. Just minutes to the Stadium, Naval ...
From $688 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Calico Cottage Guest House
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cute-as-a-bugs ear West Annapolis guest cottage. In settled neighborhood just 1.5 miles from the Navy Stadium and less t ...
From $193 per night (USD)
Expedia
From $136 per night (USD)
VRBO
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to Annapolis, where history and nature come together! Make yourself at home in this cozy 1-bedroom, 1-bath cond ...
From $136 per night (USD)
VRBO
Click For Pricing
Expedia
Annapolis House
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Traditional 4 bedroom house in neighborhood with loft. Lots of room to move around in with gated back yard. Only 3 mi ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Cute, cozy rancher close to down town Annapolis
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private location with plenty of parking. Newly renovated bathroom, french doors open to deck; great for indoor-outdoor l ...
Click For Pricing
VRBO
From $564 per night (USD)
Expedia
Modern Comfort meets Mid Century Charm at One-level home, with 4 King Beds and dog-friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Welcome to this beautifully renovated midcentury ranch home, perfectly located just 1.5 miles from the Navy-Marine Corps ...
From $564 per night (USD)
Expedia
From $455 per night (USD)
VRBO
Quiet home with large yard, close to Navy Bridge.
Bedrooms:
3
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 $455 per night (USD)
VRBO
From $308 per night (USD)
Expedia
2-bedroom waterfront Cottage in Annapolis, MD. Cove of Cork, view of the Severn.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Consider this charming cottage your home away from home while you visit Annapolis. Located on Cove of Cork, adjacent to ...
From $308 per night (USD)
Expedia
$Minutes from History: 2 Relaxing Units w\/ Free Breakfast Near Downtown Annapolis$
From $319 per night (USD)
VRBO
Minutes from History: 2 Relaxing Units w\/ Free Breakfast Near Downtown Annapolis
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $319 per night (USD)
VRBO
From $324 per night (USD)
Expedia
Annapolis Adventure: 2 Cozy Units, Outdoor Pool + Easy Access to Historic Sites!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Here, each stay is enhanced by complimentary amenities, including a hot breakfast, WiFi, and parking. Our suites provide ...
From $324 per night (USD)
Expedia
$Annapolis Luxury: Firepit \/ Deck \/ Grill$
From $536 per night (USD)
VRBO
Annapolis Luxury: Firepit \/ Deck \/ Grill
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome to our stylish new construction in the heart of Annapolis! Our home features high ceilings, contemporary decor, ...
From $536 per night (USD)
VRBO
$Minutes from History: Room w\/ Free Breakfast Near Downtown Annapolis$
From $159 per night (USD)
Expedia
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 $159 per night (USD)
Expedia
From $176 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 $176 per night (USD)
VRBO
$Annapolis Adventure: Room w\/ Outdoor Pool + Easy Access to Historic Sites$
From $163 per night (USD)
Expedia
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 $163 per night (USD)
Expedia
From $168 per night (USD)
VRBO
Experience Historical Annapolis + Complimentary Breakfast! Outdoor Pool!
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 $168 per night (USD)
VRBO
From $594 per night (USD)
Expedia
Annapolis Home Near Beach & Quiet Waters Park!
Bedrooms:
3
Bathrooms:
6
Sleeps:
13
2,552 Sq Ft | Dog Friendly w/ Fee | Wood-Burning Fireplace | 4 Mi to Downtown Annapolis Nestled just 2 miles from the C ...
From $594 per night (USD)
Expedia
From $733 per night (USD)
VRBO
DISCOUNTED FOR USNA COMMISSIONING WEEK 2024 and 2025! Short term and weekends.
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Beautiful, remodeled 3 BR home with stunning great room addition, 20' x 20' screened, covered porch with newly added out ...
From $733 per night (USD)
VRBO
From $345 per night (USD)
Expedia
Lovely contemporary in water-privileged community
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Well-furnished contemporary home, great for families, located in a quiet family-friendly neighborhood. This home has 3 ...
From $345 per night (USD)
Expedia

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Results: 437 Rentals