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Annapolis Rentals

$Cozy Bungalow w\/ Ample Outdoor Space Near Downtown$
From $247 per night (USD)
VRBO
Cozy Bungalow w\/ Ample Outdoor Space Near Downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to my charming Annapolis home in Eastport! My cozy 1 bed/1 bath house features a versatile spare room perfect fo ...
From $247 per night (USD)
VRBO
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Expedia
USNA Commissioning Week - 2 Blocks Away
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Host the perfect USNA Commissioning week family get together - just two blocks from the Naval Academy! Modern convenienc ...
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Expedia
From $356 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 $356 per night (USD)
VRBO
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Expedia
Private patio, parking, dog and family-friendly at professionally-designed On Cloud 9
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Welcome to this stunning home in downtown Annapolis with all the things you will ever need: parking for 2 cars (1 on-sit ...
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Expedia
From $931 per night (USD)
VRBO
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Bedrooms:
3
Bathrooms:
4
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 $931 per night (USD)
VRBO
$Unique Listing! Entire Downtown Triplex w\/Private Parking. Sleeps 12-18. Pets ok$
From $1026 per night (USD)
Expedia
Unique Listing! Entire Downtown Triplex w\/Private Parking. Sleeps 12-18. Pets ok
Bedrooms:
6
Bathrooms:
6
Sleeps:
18
*** Commissioning Wk 2024 AVAILABLE*** Unique opportunity to rent an entire triplex Downtown Annapolis! One property wi ...
From $1026 per night (USD)
Expedia
From $983 per night (USD)
VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
Bedrooms:
4
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 $983 per night (USD)
VRBO
From $896 per night (USD)
Expedia
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)
Expedia
From $587 per night (USD)
VRBO
3 bdrm close to city center, great yard & parking!
Bedrooms:
3
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 $587 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 $342 per night (USD)
VRBO
Comfortable Townhouse Minutes from City Dock and US Naval Academy!
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Make this well-appointed townhouse your home away from home in the family-friendly Hunt Meadow community conveniently lo ...
From $342 per night (USD)
VRBO
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 $1423 per night (USD)
Expedia
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 $1423 per night (USD)
Expedia
From $180 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 $180 per night (USD)
VRBO
From $635 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 $635 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 $636 per night (USD)
VRBO
Book for CW 2025 Walk to Main Street restaurants and shops from waterfront Condo w Pool and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Still available for Commissioning Week 2025! This beautifully-renovated and designed 2-bedroom/2-bath condo feels like ...
From $636 per night (USD)
VRBO
From $665 per night (USD)
Expedia
History & Charm steps from Main Street and City Dock
Bedrooms:
3
Bathrooms:
5
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 $665 per night (USD)
Expedia
From $931 per night (USD)
VRBO
Luxe Houseboat: Breathtaking Skyline 360 Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
| OVERVIEW | Welcome to FLOHOM 1 | Bay Escape, your home away from shore! Our luxury houseboat is docked at the premie ...
From $931 per night (USD)
VRBO
From $788 per night (USD)
Expedia
3 Story Stunner in Murray Hill <1 mile from USNA!
Bedrooms:
4
Bathrooms:
7
Sleeps:
14
Summary: This is an *amazing* 3 story / 5 bedroom house with a finished basement! This is the perfect house for a large ...
From $788 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 $1376 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 $1376 per night (USD)
Expedia
From $1077 per night (USD)
VRBO
Historic Annapolis With Parking
Bedrooms:
3
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
$Dog-friendly house with yard, deck, firepit, washer\/dryer & AC - near golf$
From $814 per night (USD)
Expedia
Dog-friendly house with yard, deck, firepit, washer\/dryer & AC - near golf
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Seas The Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $814 per night (USD)
Expedia
From $1264 per night (USD)
VRBO
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)
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
$Historic district home, View of the Capital, WALK Downtown, w\/ Outdoor Dining!$
From $627 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 $627 per night (USD)
VRBO
From $449 per night (USD)
Expedia
Belle By The Bay Summ
Bedrooms:
3
Bathrooms:
4
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 $449 per night (USD)
Expedia
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VRBO
Quiet dog-friendly suburban home with patio, grill, yard, kitchen, & Pack-N-Play
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Admiral's Glen Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
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VRBO
From $674 per night (USD)
Expedia
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)
Expedia
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VRBO
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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VRBO
From $1036 per night (USD)
Expedia
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 $1036 per night (USD)
Expedia
$Spacious Good-Value Accommodation! w\/ Outdoor Pool, Pet-Friendly, Free Parking$
From $691 per night (USD)
VRBO
Spacious Good-Value Accommodation! w\/ Outdoor Pool, Pet-Friendly, Free Parking
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 $691 per night (USD)
VRBO
From $345 per night (USD)
Expedia
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 $345 per night (USD)
Expedia
From $360 per night (USD)
VRBO
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)
VRBO
From $1226 per night (USD)
Expedia
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 $1226 per night (USD)
Expedia
From $326 per night (USD)
VRBO
Historic Home with Parking Steps From Capital & USNA
Bedrooms:
2
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 $796 per night (USD)
Expedia
Charming West Annapolis Cottage home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: This two-bedroom home in West Annapolis is a charming residence that boasts a spacious back yard, providing amp ...
From $796 per night (USD)
Expedia
From $466 per night (USD)
VRBO
Charming Charles Retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Welcome to our vacation rental nestled in the heart of Downtown Annapolis. Immerse yourself in the rich history ...
From $466 per night (USD)
VRBO
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Expedia
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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Expedia
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VRBO
Walk Everywhere! Your Ultimate Annapolis Retreat on Horn Point
Bedrooms:
3
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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VRBO
From $847 per night (USD)
Expedia
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)
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
$Downtwn Stylish 3BR\/2BA with Exclusive Parking in Annapolis-USNA Stadium$
From $376 per night (USD)
VRBO
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)
VRBO
$Restful and Charming Home in Eastport\n$
From $399 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 $399 per night (USD)
Expedia
From $632 per night (USD)
VRBO
The Crabby Patty Summ
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Nestled in the heart of historic downtown Annapolis, this three-bedroom home offers a perfect blend of modern c ...
From $632 per night (USD)
VRBO
From $511 per night (USD)
Expedia
AVAILABLE FOR COMMISSIONING WEEK! Parking, EV charger, and just steps to the Stadium!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
NBS23-145253 EXCLUSIVE COMMISSIONING WEEK RENTAL - STEPS FROM NAVY- STADIM Please note: IF YOU REQUEST TO BOOK THI ...
From $511 per night (USD)
Expedia
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VRBO
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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VRBO
From $575 per night (USD)
Expedia
Pet Friendly - Stone's throw from City Dock w private back patio
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This well-appointed recently-renovated home in the heart of Annapolis is located just steps from both the Capitol and Ci ...
From $575 per night (USD)
Expedia
From $914 per night (USD)
VRBO
Historic downtown townhome with brick courtyard, sunroom & parking
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
The Corner Courtyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $914 per night (USD)
VRBO
From $852 per night (USD)
Expedia
Luxury home walkable to restaurants, shops and stadium in West Annapolis with backyard and parking
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Welcome to Your Luxury West Annapolis Retreat! Nestled in the heart of West Annapolis, this beautifully remodeled crafts ...
From $852 per night (USD)
Expedia
From $348 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 $348 per night (USD)
VRBO
From $463 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 $463 per night (USD)
Expedia
From $482 per night (USD)
VRBO
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Bedrooms:
3
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 $1280 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 $1280 per night (USD)
Expedia
From $237 per night (USD)
VRBO
Home 2 Stay
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This 2 bedroom condo has lots of extra space for your Annapolis stay. Fully stocked galley kitchen, master suite, washer ...
From $237 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
From $589 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 $589 per night (USD)
VRBO
From $607 per night (USD)
Expedia
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 $607 per night (USD)
Expedia
Click For Pricing
VRBO
WALK TO DOWNTOWN ANNAPOLIS, EGO ALLEY, NAVAL STADIUM & ACADEMY
Bedrooms:
4
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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VRBO
From $344 per night (USD)
Expedia
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)
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
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
$Gorgeous & bright retreat with patio, firepit, W\/D, & stunning rooftop views$
From $477 per night (USD)
VRBO
Gorgeous & bright retreat with patio, firepit, W\/D, & stunning rooftop views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Skyline Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $477 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 $529 per night (USD)
VRBO
Cute bungalow blocks to Stadium
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: This stylish two bedroom home is conveniently located in Annapolis' Germantown neighborhood off West Street, ne ...
From $529 per night (USD)
VRBO
From $2274 per night (USD)
VRBO
Elegant Eastport Entertaining Dream House
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
NBS23-145363 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $2274 per night (USD)
VRBO
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
From $1566 per night (USD)
Expedia
Marvelous Home with Backyard Living Room in Murray Hill
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
NBS23-145336 Welcome to our charming vacation rental house nestled in the picturesque Murray Hill neighborhood of Annapo ...
From $1566 per night (USD)
Expedia
From $1027 per night (USD)
VRBO
Eastport Oasis 4 BR 2 BA fully renovated home on quiet street with parking
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 $1027 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 $726 per night (USD)
Expedia
Restriction Retreat - Relax & walk to Main St
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an u ...
From $726 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 $603 per night (USD)
Expedia
Steps from USNA Gates 1 & 3 with large private patio
Bedrooms:
2
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 $603 per night (USD)
Expedia
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VRBO
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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VRBO
From $314 per night (USD)
Expedia
Bay Ridge house by Quiet Waters Park, Thomas Point Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Brand new home with comfortable beds, open floor plan with kitchen excellent for entertaining, and fully equipped. All f ...
From $314 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 $313 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 $313 per night (USD)
Expedia
From $1565 per night (USD)
VRBO
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)
VRBO
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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 ...
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Expedia
From $1126 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 $1126 per night (USD)
VRBO
From $1011 per night (USD)
Expedia
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)
Expedia
$Summer Special in Annapolis! Pristine, Peaceful, Walkable 1B\/1B Apt. Sleeps 4.$
From $273 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 $273 per night (USD)
VRBO
From $473 per night (USD)
Expedia
3-bedroom vacation home in Downtown Annapolis, mins walk to U.S. Naval Academy
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover this delightful three-bedroom retreat nestled in the heart of historic Annapolis! Just a 17-minute walk to the ...
From $473 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 $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 $920 per night (USD)
VRBO
Large House Downtown Annapolis with 2 Hot Tubs and 4 parking places
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
This Navy Themed house is located jn downtown annapolis, walking distance to all the shops and restaurants in annapolis ...
From $920 per night (USD)
VRBO
From $1589 per night (USD)
Expedia
Special Pricing - Spring Sailboat Show! Save $200 on a 2 Night Stay! April 22-27 bookings only.
Bedrooms:
4
Bathrooms:
5
Sleeps:
15
RENT-000856-2025 THIS PROPERTY IS MANAGED BY ANNAPOLIS ACOCMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM M ...
From $1589 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Water-view condo with rooftop pool & balcony - minutes from downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
USNA Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $387 per night (USD)
VRBO
From $350 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 $350 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:
3
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
$Upscale home in Eastport \/ Annapolis$
From $1375 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 $1375 per night (USD)
VRBO
$Charming 3-bedroom house with AC and WiFi in enchanting Annapolis\/Eastport$
From $872 per night (USD)
Expedia
Charming 3-bedroom house with AC and WiFi in enchanting Annapolis\/Eastport
Bedrooms:
3
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 $872 per night (USD)
Expedia

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