
Severn River Rentals

- From $988 per night (USD)
VRBO
WATERFRONT Historic Home on the Chesapeake Bay
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
WATERFRONT - Beautiful 4 bedroom, 2 1/2 bathrooms newly renovated charming historic home ON the Chesapeake Bay. New mode ...
From $988 per night (USD)VRBO
- Click For Pricing
Expedia
Annapolis House
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 PricingExpedia
- From $642 per night (USD)
VRBO
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This new 4 bed / 3 bath modern luxury home sleeps 10 and is located in a quiet neighborhood near the Westin Hotel. Once ...
From $642 per night (USD)VRBO
- From $291 per night (USD)
VRBO
Annapolis Garden Suite
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our little oasis! We're tucked away on a beautiful residential street yet 7 minutes away from restaurants, co ...
From $291 per night (USD)VRBO
- From $896 per night (USD)
VRBO
Custom New Home in Eastport. Less than one mile to Naval Academy and City Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by the host ...
From $896 per night (USD)VRBO
- From $434 per night (USD)
Expedia
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Custom home with inlaid floor, wood counters, hand made cabinets, and artistic touches. Beautifully landscaped large pri ...
From $434 per night (USD)Expedia
- From $721 per night (USD)
VRBO
Steps to USNA and Main St with Private Patio and Parking at Historic Gem
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Take a stroll along the brick-lined sidewalks of Prince George Street in the Historic District and to this fully-renovat ...
From $721 per night (USD)VRBO
- From $241 per night (USD)
VRBO
Annapolis Tree House Apartment- luxury shower, separate space
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This private treehouse apartment, located above a detached garage, is nestled among the treetops on a wooded acre of lan ...
From $241 per night (USD)VRBO
- From $501 per night (USD)
VRBO
Stylish Midcentury Ranch Pet-Friendly Home Just 1.5 Miles from Navy Stadium One-Level Living
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Stylish Midcentury Ranch Just 1.5 Miles from Navy Stadium! This beautifully renovated 4BR/2BA home is perfectly located ...
From $501 per night (USD)VRBO
- From $584 per night (USD)
Expedia
Historic Downtown Union House with Free Off-Site 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 $584 per night (USD)Expedia
- From $366 per night (USD)
VRBO
Cozy Annapolis Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in the heart of Annapolis. Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly r ...
From $366 per night (USD)VRBO
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Expedia
Cheerful 1 bedroom w pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Cozy one bedroom with pool outdoor eating space and expansive yard for the kids to play in. Private bedroom, bathroom, a ...
Click For PricingExpedia
- From $620 per night (USD)
VRBO
Recently Renovated Annapolis Home - Conveniently Located
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This is the perfect getaway home for an enjoyable and relaxing stay in Annapolis. It is conveniently located within walk ...
From $620 per night (USD)VRBO
- From $417 per night (USD)
Expedia
Spectacular Location: State Circle Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Stay in this iconic building at the intersection of State Circle and Maryland Avenue in the Historic District of Annapol ...
From $417 per night (USD)Expedia
- From $773 per night (USD)
VRBO
Eastport Historic Firehouse with Parking, Dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in ...
From $773 per night (USD)VRBO
- From $622 per night (USD)
Expedia
Parking & Pet Friendly USNA-themed Annapolis home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This Naval Academy-themed 3 Bedroom home was just fully renovated and is ready to host Annapolis visitors! There are mul ...
From $622 per night (USD)Expedia
- From $826 per night (USD)
VRBO
Cozy, waterfront, 5BR 4BA house w 2 decks near USNA & downtown
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This clean, peaceful, 5 BR, 4 BA house features a waterfront view from 2 spacious decks in a quiet community. Perfect fo ...
From $826 per night (USD)VRBO
- From $350 per night (USD)
Expedia
Annapolis Condominium in the heart of the historic center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Don’t miss our unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with tw ...
From $350 per night (USD)Expedia
- Click For Pricing
VRBO
Chic Condo w/ Balcony in the Heart of Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essential ...
Click For PricingVRBO
- From $563 per night (USD)
VRBO
The Liberty House- Pristine Renovation with parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Liberty House ! Tucked away in the Murray Hill section of downtown Annapolis this home is a spacious retreat ...
From $563 per night (USD)VRBO
- From $576 per night (USD)
VRBO
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to East Street ! We invite you come spend some time at our gorgeous large home in the heart of the Historic Dist ...
From $576 per night (USD)VRBO
- From $303 per night (USD)
Expedia
Charming Historic Townhouse Steps From USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to our charming home nestled next to the prestigious Naval Academy in Annapolis. This inviting 1-bedroom, 1-bath ...
From $303 per night (USD)Expedia
- From $422 per night (USD)
VRBO
Location Location Location!!!50 Steps from Main Street and all of the action
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
We welcome you to check out our newest listing in the heart of the Historic District with the BEST front porch in downto ...
From $422 per night (USD)VRBO
- Click For Pricing
Expedia
Historic Annapolis Home Convenient to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
Click For PricingExpedia
- From $570 per night (USD)
VRBO
All-stop. Rental Midships.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome ste ...
From $570 per night (USD)VRBO
- From $413 per night (USD)
Expedia
Annapolis Downtown Entire Townhome 3 bed 6 guests
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while stayin ...
From $413 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- From $1318 per night (USD)
Expedia
Parking at Randall House Across from USNA Gate 1
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The R ...
From $1318 per night (USD)Expedia
- Click For Pricing
VRBO
5 BDRM across from the USNA Stadium
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 per ...
Click For PricingVRBO
- From $1819 per night (USD)
Expedia
Stunning Waterfront Home in Round Bay with multiple living spaces
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Available for Boat Shows! Ask us about the option to add on the 5th bedroom. This beautiful home with unobstructed view ...
From $1819 per night (USD)Expedia
- From $376 per night (USD)
VRBO
Adorable home steps from Navy Stadium!
- Bedrooms:
- 3
- 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)VRBO
- From $218 per night (USD)
VRBO
Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A beautiful basement apartment in the city of Annapolis, in the quiet Eastport neighborhood, a walk to marinas, historic ...
From $218 per night (USD)VRBO
- From $294 per night (USD)
VRBO
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
- Bedrooms:
- 1
- 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 $294 per night (USD)VRBO
- From $769 per night (USD)
Expedia
Riverfront home with multiple decks, central AC, washer/dryer - two dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Chase Creek Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $769 per night (USD)Expedia
- From $1418 per night (USD)
VRBO
3-story, dog-friendly home near beaches with home theatre, grill & gaming tables
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 15
Bella Chateau Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1418 per night (USD)VRBO
- Click For Pricing
Expedia
Newly renovated downtown home with patio, gas grill, and gas fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Blue Angel's Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
Click For PricingExpedia
- From $924 per night (USD)
VRBO
Updated historic home with parking; near Academy, college & harbor - central AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Anchors Aweigh Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $924 per night (USD)VRBO
- From $1064 per night (USD)
Expedia
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The Ship's Bridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1064 per night (USD)Expedia
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VRBO
Beach House (Annapolis) Bay Ridge Community
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Relax on the front porch while enjoying sweeping views of the Chesapeake Bay. Enjoy the beach right in front of house. P ...
Click For PricingVRBO
- From $1024 per night (USD)
Expedia
Private Pier Waterfront Jolly Roger mins to DTA
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Arrive by car or boat to this waterfront home, located in Crownsville, just outside of Annapolis. The private pier is o ...
From $1024 per night (USD)Expedia
- From $257 per night (USD)
VRBO
Well-appointed 1 bedroom, 1 bath in Annapolis / Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This spacious, well-appointed 1 bedroom, 1 European style bath 2nd floor apartment is in the heart of Eastport. You’ll b ...
From $257 per night (USD)VRBO
- From $792 per night (USD)
VRBO
Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
BOOK YOUR ANNAPOLIS VACATION AT BURLEY CREEK HIDEAWAY! Charming home owned by USNA grads. Lovely waterfront two-level ...
From $792 per night (USD)VRBO
- From $329 per night (USD)
VRBO
Annapolis-Eastport Cottage Home - Walk Everywhere - RV Van Parking & Hook-up too
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Walk to all Annapolis has to offer, once parked you’ll never need a car. Walk to City Dock, marinas, restaurants, pubs ...
From $329 per night (USD)VRBO
- From $463 per night (USD)
Expedia
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Charming private space in a quiet neighborhood. Live like locals and enjoy walking or biking around town. Free street p ...
From $463 per night (USD)Expedia
- From $634 per night (USD)
VRBO
Charm & Style in this Renovated Eastport Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience a cozy retreat in this inviting 3-bedroom, 2-bathroom cottage, just 3 blocks from the historic Spa Creek Brid ...
From $634 per night (USD)VRBO
- From $866 per night (USD)
Expedia
1 Block to USNA at beautifully renovated Historic Chapel Views with back patio and off-site parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s ...
From $866 per night (USD)Expedia
- From $334 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 $334 per night (USD)VRBO
- From $382 per night (USD)
VRBO
Your Annapolis Adventure Starts Here!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
From $382 per night (USD)VRBO
- From $751 per night (USD)
VRBO
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $751 per night (USD)VRBO
- From $299 per night (USD)
Expedia
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 $299 per night (USD)Expedia
- From $513 per night (USD)
VRBO
Go Navy! Steps to USNA, City Dock & Street Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Stay in the heart of Historic Annapolis just steps from the waterfront, shops, restaurants, and the Naval Academy. Owned ...
From $513 per night (USD)VRBO
- From $713 per night (USD)
Expedia
Private Patio at Charming Hanover House Across from USNA Gate 3
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a ...
From $713 per night (USD)Expedia
- From $264 per night (USD)
VRBO
Bay View Studio Apartment
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $264 per night (USD)VRBO
- From $1165 per night (USD)
Expedia
Quiet home with large yard, close to Navy Bridge.
- Bedrooms:
- 2
- 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 $1165 per night (USD)Expedia
- From $1004 per night (USD)
VRBO
USNA Stay w/ Private Pool, King Beds, Furbabies & CHILD FRIENDLY GEAR
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
USNA Family Stay w/Pool - Infant/Toddler Friendly! Enjoy the newest addition to my “Family Friendly Staycation” home ho ...
From $1004 per night (USD)VRBO
- From $418 per night (USD)
Expedia
Easy Annapolis lodging - still available for Sailboat Show!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This home (divided/upper floor only) is perfect for families, situated on a quiet residential street with a gorgeous bac ...
From $418 per night (USD)Expedia
- From $397 per night (USD)
VRBO
ACROSS FROM STADIUM - walk to downtown Annapolis.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Across the street from the Navy and Marine Corps Stadium and walking distance to historic downtown Annapolis - you will ...
From $397 per night (USD)VRBO
- From $459 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 $459 per night (USD)VRBO
- From $871 per night (USD)
VRBO
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Harrison Hall Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $871 per night (USD)VRBO
- From $1002 per night (USD)
Expedia
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to Modern Elegance in Historic Annapolis Step into this fully-renovated 1900s home, where modern sophistication ...
From $1002 per night (USD)Expedia
- From $506 per night (USD)
VRBO
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
421 Irie City Of Annapolis License Number 145052 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! ...
From $506 per night (USD)VRBO
- From $441 per night (USD)
Expedia
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come enjoy a relaxing stay in our coastal waterfront cottage in Epping Forest! Just steps from a community pier perfec ...
From $441 per night (USD)Expedia
- From $360 per night (USD)
VRBO
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Amongst the allure of downtown living, lies this quant Annapolis home. This two bedroom, one and a half bath has a spaci ...
From $360 per night (USD)VRBO
- From $3784 per night (USD)
Expedia
Lakefront home with private dock, deck, hot tub, firepit, Ping-Pong, large yard
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 16
Base Camp on the Lake Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $3784 per night (USD)Expedia
- From $1774 per night (USD)
VRBO
Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
The Morning Watch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1774 per night (USD)VRBO
- From $1626 per night (USD)
Expedia
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
The Admiral's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1626 per night (USD)Expedia
- From $1518 per night (USD)
VRBO
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The Master Shipwright Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1518 per night (USD)VRBO
- From $475 per night (USD)
VRBO
Stunning Waterfront Cottage with Breathtaking Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in t ...
From $475 per night (USD)VRBO
- From $465 per night (USD)
VRBO
Large Luxury Apartment In Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2 Bed/2 Bath Apartment with additional family room with brand new queen sleeper sofa in Historic Downtown Annapolis step ...
From $465 per night (USD)VRBO
- From $753 per night (USD)
VRBO
Waterfront Oasis in Eastport-Easy Walk to Downtown
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. With 4 bedrooms and an open studio spac ...
From $753 per night (USD)VRBO
- From $456 per night (USD)
VRBO
PERFECT LOCATION in the heart of history
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Be our guest at Historic 19 East Street, in the heart of the Annapolis national landmark district. Walk out the front d ...
From $456 per night (USD)VRBO
- From $370 per night (USD)
VRBO
Walk everywhere . . .just minutes to historic Annapolis, Updated.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A modern historic gem in a 10 unit building in Eastport or as the locals call it the Maritime Republic of Eastport or "M ...
From $370 per night (USD)VRBO
- From $556 per night (USD)
VRBO
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to your dream stay nestled in the heart of Historic Downtown Annapolis! Located just 45 feet from downtown Anna ...
From $556 per night (USD)VRBO
- From $513 per night (USD)
VRBO
Heart of Historic District!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This three story 1875 home is located in the Heart of Historic Annapolis. Shops, restaurants, historic sites and the Cit ...
From $513 per night (USD)VRBO
- From $188 per night (USD)
VRBO
Beautiful Condo - Water View Near City Dock
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Check out our winter rates for January, February and March! The Newport Condominium has a beautiful water view of Spa ...
From $188 per night (USD)VRBO
- From $525 per night (USD)
Expedia
Jackson's Bunker in Eastport with fenced-in backyard and dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Located in the Annapolis "Republic of Eastport", this charming pet-friendly home is a short walk to restaurants, shops, ...
From $525 per night (USD)Expedia
- From $855 per night (USD)
VRBO
Charming 239-year-old former tavern 1 block to water & shops
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
239-year-old home, formerly a tavern & inn where Thomas Jefferson bought salt & stockings. Beautifully furnished with an ...
From $855 per night (USD)VRBO
- From $254 per night (USD)
Expedia
Pristine Downtown 1-Bedroom Steps from State House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy your stay in the heart of Annapolis's historic district, steps away from the Maryland State House and a few minute ...
From $254 per night (USD)Expedia
- From $490 per night (USD)
VRBO
Annapolis Vacation Home: 2 Mi to Quiet Waters Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The Chesapeake Bay awaits you at this Annapolis vacation rental! 'Admiral's Post' is situated under 4 miles from the cit ...
From $490 per night (USD)VRBO
- From $722 per night (USD)
Expedia
USNA Home Steps to Stadium Dog-Friendly w Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
In Navy jargon, the goat locker is a lounge, sleeping area, and galley on board a naval vessel which is reserved for the ...
From $722 per night (USD)Expedia
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VRBO
USNA Commissioning Week 2023 Downtown Annapolis House that sleeps 13 people
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
This 3 story half duplex is in the perfect location, situated in historical downtown Annapolis with a modern day feel, r ...
Click For PricingVRBO
- From $196 per night (USD)
Expedia
Cozy Home in Beautiful Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Keep it simple at this peaceful and centrally located Annapolis home. It has all the amenities and essentials of a home ...
From $196 per night (USD)Expedia
- From $465 per night (USD)
VRBO
Charming brick home with patio, WiFi, AC, & W/D - walk to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Little House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $465 per night (USD)VRBO
- From $1531 per night (USD)
VRBO
Annapolis Bayfront Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Beautifully restored turn of the century beach cottage located on an acre of landscaped property with magnificent views ...
From $1531 per night (USD)VRBO
- From $611 per night (USD)
VRBO
Freshly renovated 3-story home 1 block from USNA!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Welcome to The Wardroom! Originally built in 1902 and completely renovated in 2014, this 3 story home is the p ...
From $611 per night (USD)VRBO
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Expedia
Hideaway in the middle of everything
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Clean, spacious Eastport cottage in a prime location to downtown Annapolis and the United States Naval Academy. Both are ...
Click For PricingExpedia
- From $663 per night (USD)
VRBO
Multiple Gathering Spaces, Private Backyard & Free Parking at Townhome 1 Block to Capital Bldg
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Naptown Nook, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in th ...
From $663 per night (USD)VRBO
- From $869 per night (USD)
Expedia
MODERN 2022 NEWLY BUILT TOWNHOME
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two li ...
From $869 per night (USD)Expedia
- From $323 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 $323 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 $531 per night (USD)
VRBO
Escape Villa in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Do ...
From $531 per night (USD)VRBO
- Click For Pricing
Expedia
Serene, riverfront home with deck, balcony, kitchen & fireplace - dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Severn View of Serenity Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For PricingExpedia
- From $361 per night (USD)
VRBO
Modern studio apartment 5 minute walk to downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Modern efficiency apartment with king bed, seating area with 2 recliner chairs for watching TV. Set up for remote work ...
From $361 per night (USD)VRBO
- From $1202 per night (USD)
Expedia
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The location is ideal - one short block to USNA Gate 3, and just 4 blocks to the downtown waterfront. Home has a privat ...
From $1202 per night (USD)Expedia
- Click For Pricing
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 ...
Click For PricingVRBO
- Click For Pricing
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 ...
Click For PricingExpedia
- Click For Pricing
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 ...
Click For PricingVRBO
- From $400 per night (USD)
Expedia
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)Expedia
- 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