
Severn River Rentals

- From $400 per night (USD)
VRBO
Chesapeake Comfort, Annapolis.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Annapolis Bungalow Home that is professionally cleaned and is a full time short-term rental. I have been a Superhost wit ...
From $400 per night (USD)VRBO
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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 ...
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- From $2669 per night (USD)
VRBO
Upscale multi-level retro home with large deck, washer/dryer, and lovely patio
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
St Johns Adjacent Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $2669 per night (USD)VRBO
- From $1743 per night (USD)
Expedia
3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 12
Ensign's Ridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1743 per night (USD)Expedia
- From $1075 per night (USD)
VRBO
Huge deck overlooking water
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Renovated, charming Annapolis home on half-acre lot fronting Burley Creek. Just a short paddle to Whitehall Bay and expa ...
From $1075 per night (USD)VRBO
- From $369 per night (USD)
Expedia
Annapolis Charm –Bright 3BR in Downtown
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Private 3 floor house located at the edge of Annapolis historic district. You can be certain that you will have all the ...
From $369 per night (USD)Expedia
- From $888 per night (USD)
VRBO
Annapolis 4 BR w/ Gameroom & fire pits-walk everywhere!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
This is the perfect house for your family friendly visit to Annapolis, MD Enjoy everything the sought after Eastport ne ...
From $888 per night (USD)VRBO
- From $394 per night (USD)
VRBO
Charming 1926 Four Bedroom Home w Ample Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought ou ...
From $394 per night (USD)VRBO
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VRBO
Waterfront Magic - 10 minutes from downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
A peninsula on the Severn River located in the beautiful neighborhood of Linstead. This home is a waterfront playground ...
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Expedia
Charming Historic Annapolis Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful historic home is situated directly across the street from the Paca House, and only three blocks from the ...
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VRBO
Coastal Cabins.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming & cozy, 2- level Victorian style home built in the 1920s. Well stocked w/ modern conveniences for your home awa ...
Click For PricingVRBO
- From $1326 per night (USD)
Expedia
Beautiful waterfront home on The Chesapeake Bay with private dock & beach access
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Annapolis Bay Ridge Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply e ...
From $1326 per night (USD)Expedia
- From $708 per night (USD)
VRBO
Private yard and screened porch at Historic happy home, steps to Main Street with parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic ...
From $708 per night (USD)VRBO
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Expedia
Private Eastport Guest Suite in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a clean, comfortable and private suite in the heart of Eastport. Steps away from Davis' Pub and Forward Brewing as ...
Click For PricingExpedia
- From $1102 per night (USD)
VRBO
Newly renovated historic Annapolis house. walking distance to navy stadium, DTA
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
A perfect harmony of classic and modern, this newly renovated property has a quintessential Annapolis feel. Nestled in t ...
From $1102 per night (USD)VRBO
- From $649 per night (USD)
Expedia
Waterfront home with private pier mins to Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the magnificent waterfront views from this custom-built home with a private pier! Nestled in the quiet Arden on th ...
From $649 per night (USD)Expedia
- 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:
- 2
- 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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VRBO
Elegant waterfront cottage and guest house, garden setting, clubhouse and beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy waterfront views from every window, crabbing from the pier, sundowners on the wrap around porch, set in a private ...
Click For PricingVRBO
- From $331 per night (USD)
VRBO
Perfect Eastport Location, walk everywhere, Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Leave your car behind and walk to everything Annapolis, Eastport is full of charm, Restaurants, Museums, live music. Com ...
From $331 per night (USD)VRBO
- From $961 per night (USD)
VRBO
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Be ...
From $961 per night (USD)VRBO
- From $1138 per night (USD)
VRBO
Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 18
*** Commissioning Wk 2024 AVAILABLE*** Unique opportunity to rent an entire triplex Downtown Annapolis! One property wi ...
From $1138 per night (USD)VRBO
- From $953 per night (USD)
VRBO
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
From $953 per night (USD)VRBO
- From $792 per night (USD)
Expedia
BY THE BAY
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
WATER, WATER everywhere! Our home is centrally located to all the water Bay Ridge has to offer. Our home is located jus ...
From $792 per night (USD)Expedia
- From $896 per night (USD)
VRBO
BAY RIDGE MODERN HOME WITH VINTAGE CHARM
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful spacious modern family home with vintage charm. A great gathering spot for family or just wanting to spend som ...
From $896 per night (USD)VRBO
- From $627 per night (USD)
VRBO
3 bdrm close to city center, great yard & parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Approx .7 mile to stadium, 1.4 to Naval Academy. Walk to free shuttle at Park Place and to great coffee every morning fr ...
From $627 per night (USD)VRBO
- 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 $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
Peaceful Home in Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Relax with the whole family at this peaceful place to stay. A quaint 4-bedroom home tucked away on 2.2 acres. Enjoy the ...
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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 ...
Click For PricingExpedia
- From $621 per night (USD)
VRBO
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)VRBO
- From $554 per night (USD)
VRBO
Charming Home located minutes from the Naval Academy and Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Private 4BR, 2.5BA luxurious Gem was recently upgraded, and tastefully decorated awaits your arrival. The ranch style ho ...
From $554 per night (USD)VRBO
- From $697 per night (USD)
VRBO
Serene waterfront home with kayaks, paddle board, grill, firepit, W/D, and AC
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Valentine Creek Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $697 per night (USD)VRBO
- From $556 per night (USD)
Expedia
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)Expedia
- From $656 per night (USD)
VRBO
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)VRBO
- From $923 per night (USD)
Expedia
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)Expedia
- From $1173 per night (USD)
VRBO
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)VRBO
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Expedia
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 ...
Click For PricingExpedia
- 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 $1777 per night (USD)
VRBO
Bay Ridge Beauty with Wooded Serenity and Community Water Views
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
STR00711 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $1777 per night (USD)VRBO
- From $896 per night (USD)
VRBO
Cottage for Rent
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Cottage for Rent xxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxxx ...
From $896 per night (USD)VRBO
- From $1077 per night (USD)
Expedia
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)Expedia
- From $865 per night (USD)
VRBO
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)VRBO
- From $1264 per night (USD)
Expedia
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)Expedia
- 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 $1068 per night (USD)
Expedia
Riverfront home with private dock, foosball table, fireplace, river views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Taids Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $1068 per night (USD)Expedia
- 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 $840 per night (USD)
VRBO
Waterfront home with scenic porches, yard, grill, jetted tub, central AC, & W/D
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
The Salty Crab Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $840 per night (USD)VRBO
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Expedia
Upscaled Efficiency Apartment in Private Community
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
800 sq ft of newly designed apartment with full size kitchen, full size bathroom, lots of storage space, laundry room wi ...
Click For PricingExpedia
- 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
- 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 ...
Click For PricingVRBO
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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 ...
Click For PricingExpedia
- From $2513 per night (USD)
VRBO
Beautiful 6 BR home on quiet, secluded lot, overlooking the Severn River
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
STR00749 - Heaven on the Severn � THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED ...
From $2513 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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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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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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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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Expedia
Mulberry's Gem
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This is your home away from home. All the comforts you could need. The open concept living space is the perfect spot to ...
Click For PricingExpedia
- 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
- Click For Pricing
Expedia
Cozy Arnold House Near Annapolis\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your family will be close to everything Annapolis has to offer when you stay at our cozy Arnold home. This home is locat ...
Click For PricingExpedia
- From $393 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 $393 per night (USD)VRBO
- From $692 per night (USD)
Expedia
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)Expedia
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VRBO
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 ...
Click For PricingVRBO
- From $711 per night (USD)
Expedia
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)Expedia
- From $807 per night (USD)
VRBO
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)VRBO
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Expedia
Cozy cottage, Bayridge neighborhood for rent. 2 bedrooms, 1 1/2 bathrooms.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy cottage in a serene setting. A week spent in this cottage will decompress, reset, and rejuvenate. 100 year old Cott ...
Click For PricingExpedia
- From $444 per night (USD)
VRBO
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)VRBO
- From $495 per night (USD)
Expedia
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)Expedia
- From $635 per night (USD)
VRBO
Private Waterfront Woods | Dock, Kayaks, Views
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 19
Welcome to The Compass Rose, a serene haven with backyard shoreline surrounded by 4+ acres of pristine woods. Enjoy excl ...
From $635 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
- Click For Pricing
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 ...
Click For PricingExpedia
- 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 $1681 per night (USD)
VRBO
Welcoming Waterfront Luxury Estate for Family, Friends, and Pets in Annapolis
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 14
Large Waterfront Family Estate House in an Old Oak Forest at the end of a private gated Community in Annapolis. Architec ...
From $1681 per night (USD)VRBO
- From $668 per night (USD)
Expedia
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)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- From $299 per night (USD)
Expedia
Bay Ridge house by Quiet Waters Park, Thomas Point Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Brand new home with comfortable beds, open floor plan with kitchen excellent for entertaining, and fully equipped. All f ...
From $299 per night (USD)Expedia