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

Annapolis Rentals

From $644 per night (USD)
VRBO
Fisher House - Downtown Annapolis!
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to our beautifully renovated historic home in the heart of Annapolis! The Fisher House was built in 1885 and nam ...
From $644 per night (USD)
VRBO
From $1575 per night (USD)
Expedia
USNA Luxury Home in Downtown Annapolis with local garage parking
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. We pay for ...
From $1575 per night (USD)
Expedia
From $365 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 $365 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 $721 per night (USD)
VRBO
Walk everywhere from Villa with multiple suites, dining spaces, parking
Bedrooms:
3
Bathrooms:
6
Sleeps:
10
Visit the magic of Annapolis during the Holiday Season Welcome to Naptown Villa! This charming fully-renovated home in d ...
From $721 per night (USD)
VRBO
From $532 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 $532 per night (USD)
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
From $530 per night (USD)
Expedia
Spacious 5 bedroom house in Annapolis - 3 Miles from Naval Academy
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Unwind in Annapolis at this brilliant house. With 5 cozy bedrooms featuring a mix of king, queen, and full beds, guests ...
From $530 per night (USD)
Expedia
From $600 per night (USD)
VRBO
Spacious 2-Unit Home with Parking, Private Backyard, and Dog-Friendly
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Welcome to your perfect getaway in the heart of Eastport, Annapolis! This beautifully restored 2-unit building offers fl ...
From $600 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
From $420 per night (USD)
VRBO
Dean Street Delight - Pristine Home in Historic Annapolis with Parking
Bedrooms:
4
Bathrooms:
3
Sleeps:
7
This enchanting house in Annapolis offers a nautical themed retreat in the Historic District . Featuring an open floor ...
From $420 per night (USD)
VRBO
From $1430 per night (USD)
Expedia
Downtown Annapolis Duke's House
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
This newly renovated 4-bedroom, 3.5 bathroom home is perfectly situated in the heart of historic downtown Annapolis, ma ...
From $1430 per night (USD)
Expedia
From $1187 per night (USD)
VRBO
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 $1187 per night (USD)
VRBO
From $502 per night (USD)
VRBO
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 $502 per night (USD)
VRBO
From $385 per night (USD)
VRBO
Stay on a boat while in annapolis for the shows.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Large 43' sailboat with 3 cabins, 2 bathrooms, a large cockpit and plenty of space on the deck. The boat is anchored in ...
From $385 per night (USD)
VRBO
From $390 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 $390 per night (USD)
VRBO
From $798 per night (USD)
VRBO
Classic Victorian home in the heart of Eastport
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
3 bedroom house with off street parking, friendly porch. Make yourself at home and enjoy the neighborhood! There’s a b ...
From $798 per night (USD)
VRBO
From $852 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 $852 per night (USD)
VRBO
From $799 per night (USD)
VRBO
Newly-renovated Lighthouse Inn with game room parking, private backyard, walk to downtown
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Visit the magic of Annapolis during the Holiday Season Stay in this stunning Craftsman home, just steps from the water a ...
From $799 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Historic Downtown Union House with Free parking & private patio
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Visit the magic of Annapolis during the Holiday Season Enjoy Annapolis, MD in this charming Federal-style home nestled i ...
From $481 per night (USD)
Expedia
From $735 per night (USD)
VRBO
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 $735 per night (USD)
VRBO
From $517 per night (USD)
Expedia
Steps to USNA and Main St w private patio and parking at Historic gem
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Visit the magic of Annapolis during the Holiday Season Take a stroll along the brick-lined sidewalks of Prince George St ...
From $517 per night (USD)
Expedia
From $934 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 $934 per night (USD)
VRBO
From $311 per night (USD)
Expedia
Eastport Condo in Building with Rooftop Water Views of Spa Creek!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
STR21-145036 - PLEASE NOTE: IF YOU REQUEST TO BOOK THIS PROPERTY, YOU WILL BE CONTACTED BY ANNAPOLIS ACCOMMODATIONS, T ...
From $311 per night (USD)
Expedia
From $319 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 $319 per night (USD)
VRBO
From $502 per night (USD)
Expedia
Steps to Main St at Historic Carriage House in the Heart of Downtown Annapolis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Visit the magic of Annapolis during the Holiday Season Originally built in 1857, this fully-restored home has a rich his ...
From $502 per night (USD)
Expedia
From $896 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 $896 per night (USD)
VRBO
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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 ...
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Expedia
From $817 per night (USD)
VRBO
Eastport Peninsula Charm
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Available for Powerboat show 2024. Spacious historic home in the center of Eastport peninsula. Plenty of space for ...
From $817 per night (USD)
VRBO
From $289 per night (USD)
VRBO
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 $289 per night (USD)
VRBO
From $538 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 $538 per night (USD)
VRBO
From $1553 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 $1553 per night (USD)
Expedia
From $273 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 $273 per night (USD)
VRBO
From $1366 per night (USD)
Expedia
Historic Annapolis Charmer <1Mile to NMC Stadium
Bedrooms:
5
Bathrooms:
6
Sleeps:
18
IMMACULATE SPACE AND RARE FIND IN DOWNTOWN ANNAPOLIS SLEEPING UP TO 21! Beautifully maintained 1930's home in the middl ...
From $1366 per night (USD)
Expedia
From $656 per night (USD)
VRBO
Home with garage parking & EV!!Downtown Fleet Street Carriage House
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Friends! We are a USNA family (‘92) that loves this town! Walk to bottom of our street and you are at the docks. Walk to ...
From $656 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 $390 per night (USD)
Expedia
Downtwn Stylish 3BR\/2BA with Exclusive Parking in Annapolis-USNA Stadium
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to this Annapolis gem located in the historic city of Annapolis. Enjoy living walking distance from all of the b ...
From $390 per night (USD)
Expedia
$Restful and Charming Home in Eastport\n$
From $337 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 $337 per night (USD)
VRBO
From $648 per night (USD)
Expedia
Captain's Quarters - Eastport!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Ditch the car, bring the family & dog and make this beloved and restored 1920's bungalow in the desirable maritime commu ...
From $648 per night (USD)
Expedia
From $597 per night (USD)
VRBO
Annapolis gem! Walk to Stadium & close to USNA
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Privacy and convenience!! Walk to Navy-Marine Corp Stadium, or just a few mins by car to USNA, downtown, restaurants an ...
From $597 per night (USD)
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 $484 per night (USD)
VRBO
4 Bedroom - Completely updated. Super safe neighborhood close to USNA stadium
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Not your typical Airbnb. This is our vacation house too and we have it stocked so you can enjoy all of the amenities of ...
From $484 per night (USD)
VRBO
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Expedia
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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Expedia
From $740 per night (USD)
VRBO
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 $740 per night (USD)
VRBO
From $372 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 $372 per night (USD)
Expedia
From $645 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 $645 per night (USD)
VRBO
From $490 per night (USD)
Expedia
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 $490 per night (USD)
Expedia
From $401 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 $401 per night (USD)
VRBO
From $577 per night (USD)
Expedia
Stay just steps from City Dock in the Historic Fleet's Inn
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Visit the magic of Annapolis during the Holiday Season Stay just steps from the Annapolis waterfront! Cherished by the ...
From $577 per night (USD)
Expedia
From $335 per night (USD)
VRBO
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 $335 per night (USD)
VRBO
From $537 per night (USD)
Expedia
USNA-themed dog-friendly home steps from Navy Stadium with parking
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Visit the magic of Annapolis during the Holiday Season In Navy jargon, the goat locker is a lounge, sleeping area, and g ...
From $537 per night (USD)
Expedia
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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
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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 ...
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Expedia
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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 ...
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VRBO
From $273 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 $273 per night (USD)
VRBO
From $866 per night (USD)
VRBO
Charming 238-yo former tavern 1 block to water & shops
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
238 yo home, formerly a tavern & inn where Thomas Jefferson bought salt & stockings. Beautifully furnished with antiques ...
From $866 per night (USD)
VRBO
From $518 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 $518 per night (USD)
Expedia
From $558 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 $558 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 $2915 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 $2915 per night (USD)
VRBO
From $455 per night (USD)
Expedia
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)
Expedia
From $468 per night (USD)
VRBO
Close to USNA Stadium with screened-in porch and parking
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Visit the magic of Annapolis during the Holiday Season Welcome to this charming Cape Cod on half an acre right outside d ...
From $468 per night (USD)
VRBO
From $181 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 $181 per night (USD)
Expedia
From $134 per night (USD)
VRBO
Cozy place close to the city dock
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Welcome to Annapolis; where history and nature coincide! You will feel right at home in this confortable 1 bedroom 1 bat ...
From $134 per night (USD)
VRBO
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Expedia
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 ...
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Expedia
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VRBO
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 ...
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VRBO
From $506 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
Visit the magic of Annapolis during the Holiday Season Welcome to this beautifully renovated midcentury ranch home, perf ...
From $506 per night (USD)
Expedia
From $1518 per night (USD)
VRBO
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)
VRBO
$Minutes from History: Room w\/ Free Breakfast Near Downtown Annapolis$
From $162 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 $162 per night (USD)
VRBO
From $186 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 $186 per night (USD)
VRBO
$Annapolis Adventure: Room w\/ Outdoor Pool + Easy Access to Historic Sites$
From $166 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 $166 per night (USD)
VRBO
From $512 per night (USD)
VRBO
Annapolis Home Near Beach, Dtwn & Navy Football!
Bedrooms:
3
Bathrooms:
6
Sleeps:
13
Dog Friendly w/ Fee | Wood-Burning Fireplace | 4 Mi to Downtown Annapolis Nestled just 2 miles from the Chesapeake Bay, ...
From $512 per night (USD)
VRBO
$Minutes from History: 2 Relaxing Units w\/ Free Breakfast Near Downtown Annapolis$
From $382 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 $382 per night (USD)
VRBO
From $392 per night (USD)
VRBO
Annapolis Adventure: 2 Cozy Units, Outdoor Pool + Easy Access to Historic Sites!
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 $392 per night (USD)
VRBO
$Annapolis Luxury: Firepit \/ Deck \/ Grill$
From $328 per night (USD)
Expedia
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 $328 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Experience Historical Annapolis + Complimentary Breakfast! Parking
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 $181 per night (USD)
VRBO
From $274 per night (USD)
VRBO
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 $274 per night (USD)
VRBO
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 $562 per night (USD)
VRBO
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 $562 per night (USD)
VRBO
From $251 per night (USD)
VRBO
Spacious 2nd Floor Apartment, with its own entrance and off-street parking.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STR- 270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $251 per night (USD)
VRBO
$Fully Furnished 4 Bedroom\/3 Bathroom Single Family Home in Annapolis just a few minutes from downtown$
From $487 per night (USD)
Expedia
Fully Furnished 4 Bedroom\/3 Bathroom Single Family Home in Annapolis just a few minutes from downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
STR-270 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $487 per night (USD)
Expedia
From $1350 per night (USD)
VRBO
4 BR Colonial home just outside of Annapolis - Beautiful 4 Seasons room overlooking fenced backyard with beautiful pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
STR00808 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1350 per night (USD)
VRBO
$Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w\/private dock\/pier\/ private pool and kayaks.$
From $1241 per night (USD)
Expedia
Contemporary waterfront 4BR home close to downtown Annapolis - stunning water views w\/private dock\/pier\/ private pool and kayaks.
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
STR259 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1241 per night (USD)
Expedia
From $312 per night (USD)
VRBO
The Yellow Cottage on Harness Creek
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
The minute you step into our charming waterfront cottage you will feel right at home! Situated on Harness Creek, in a q ...
From $312 per night (USD)
VRBO
From $1382 per night (USD)
Expedia
Stunning colonial p on a private 1.6 acre lot situated on Broadneck Peninsula.
Bedrooms:
4
Bathrooms:
5
Sleeps:
9
STR00844 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1382 per night (USD)
Expedia
From $513 per night (USD)
VRBO
Great Entertaining Spot for any Occassion!
Bedrooms:
1
Bathrooms:
2
Sleeps:
10
This newly built 2012 Carriage House has all the bells and whistles for a relaxed fiiends and family stay. Enjoy this u ...
From $513 per night (USD)
VRBO
From $1359 per night (USD)
Expedia
Hidden Treasure on Weems Creek
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
STR00704 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $1359 per night (USD)
Expedia
From $549 per night (USD)
VRBO
Marymont Cottage in awesome Annapolis walking distance to local pub!
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Discover this adorable 3-bedroom gem in Annapolis, just across the creek from sought after West Annapolis. This charming ...
From $549 per night (USD)
VRBO
Click For Pricing
Expedia
Stunning Waterfront Home with Incredible Views
Bedrooms:
6
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 $1276 per night (USD)
VRBO
Beautiful 7BR home minutes from downtown Annapolis
Bedrooms:
6
Bathrooms:
7
Sleeps:
14
Newly renovated modern colonial on several acres just minutes from downtown Annapolis and the Naval Academy. Chefs kitch ...
From $1276 per night (USD)
VRBO
From $1261 per night (USD)
VRBO
Waterfront Architectural Masterpiece with private dockage available.
Bedrooms:
5
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 $896 per night (USD)
VRBO
BAY RIDGE MODERN HOME WITH VINTAGE CHARM
Bedrooms:
3
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 $1059 per night (USD)
VRBO
Luxury Waterfront Annapolis home with your very own Private Beach & Dock
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
About this space Stunning Contemporary Home with private beach! House has been listed on another site receiving five st ...
From $1059 per night (USD)
VRBO
From $304 per night (USD)
VRBO
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
Bedrooms:
2
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 $304 per night (USD)
VRBO
From $553 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 $553 per night (USD)
Expedia
From $162 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 $162 per night (USD)
VRBO
From $1264 per night (USD)
Expedia
Beautiful colonial only 3 miles to the Naval Academy!
Bedrooms:
3
Bathrooms:
5
Sleeps:
11
Beautiful colonial perfect for Naval Academy commissioning week! Bedrooms 6 - Baths: 2.5 Sleeps 11 comfortably. Finish ...
From $1264 per night (USD)
Expedia

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