Annapolis Rentals
From $399 per night (USD)VRBO
The Very Best location - 50 Steps from Main Street
- 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 $399 per night (USD)VRBO
From $559 per night (USD)Expedia
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 $559 per night (USD)Expedia
From $413 per night (USD)VRBO
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)VRBO
Click For PricingExpedia
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 PricingExpedia
From $1267 per night (USD)VRBO
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 $1267 per night (USD)VRBO
Click For PricingExpedia
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 PricingExpedia
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 $197 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 $197 per night (USD)VRBO
Click For PricingVRBO
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 PricingVRBO
From $805 per night (USD)Expedia
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 $805 per night (USD)Expedia
Click For PricingVRBO
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 $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 $327 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 $327 per night (USD)VRBO
From $499 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 $499 per night (USD)Expedia
From $579 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 $579 per night (USD)VRBO
From $655 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 $655 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 $408 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 $408 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 $473 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 $473 per night (USD)VRBO
From $683 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 $683 per night (USD)Expedia
From $314 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 $314 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 $418 per night (USD)VRBO
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)VRBO
From $384 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 $384 per night (USD)VRBO
From $1011 per night (USD)VRBO
Serene Sunsets at Historic Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sit ...
From $1011 per night (USD)VRBO
From $442 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 $442 per night (USD)VRBO
From $651 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 $651 per night (USD)VRBO
From $1007 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 $1007 per night (USD)Expedia
From $498 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 $498 per night (USD)VRBO
From $1605 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 $1605 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 $449 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 $449 per night (USD)VRBO
From $518 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 $518 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 $449 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 $449 per night (USD)VRBO
From $328 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 $328 per night (USD)VRBO
From $527 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 $527 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 $195 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 $195 per night (USD)VRBO
From $689 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 $689 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 $471 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 $471 per night (USD)VRBO
From $735 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 $735 per night (USD)Expedia
Click For PricingVRBO
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 $182 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 $182 per night (USD)Expedia
From $282 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 $282 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
Click For PricingVRBO
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 PricingVRBO
From $668 per night (USD)Expedia
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 $668 per night (USD)Expedia
From $1040 per night (USD)VRBO
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 $1040 per night (USD)VRBO
From $215 per night (USD)VRBO
Waterfront Condo- Eastport Annapolis- Next to Spa Creek Draw Bridge & AYC
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $215 per night (USD)VRBO
From $540 per night (USD)VRBO
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)VRBO
From $543 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 $543 per night (USD)VRBO
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 $1088 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 $1088 per night (USD)Expedia
Click For PricingVRBO
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 PricingExpedia
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 PricingVRBO
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 $458 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 $458 per night (USD)Expedia
From $2018 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 $2018 per night (USD)VRBO
From $2726 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 $2726 per night (USD)Expedia
From $262 per night (USD)VRBO
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 $262 per night (USD)VRBO
From $768 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 $768 per night (USD)VRBO
Click For PricingVRBO
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 $689 per night (USD)Expedia
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 $689 per night (USD)Expedia
Click For PricingVRBO
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 PricingVRBO
Click For PricingExpedia
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 ...
Click For PricingExpedia
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 $937 per night (USD)Expedia
Beachfront Home Minutes to Downtown Annapolis 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 $937 per night (USD)Expedia
From $986 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 $986 per night (USD)VRBO
From $809 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 $809 per night (USD)VRBO
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 $606 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 $606 per night (USD)VRBO
From $347 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 $347 per night (USD)VRBO
From $684 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 $684 per night (USD)Expedia
From $500 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 $500 per night (USD)VRBO
From $1261 per night (USD)VRBO
Waterfront Architectural Masterpiece with private dockage available.
- Bedrooms:
- 4
- 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 $127 per night (USD)VRBO
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Modern family units with private kitchens for the ultimate Annapolis experience This listing is for a room within a hot ...
From $127 per night (USD)VRBO
From $566 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 $566 per night (USD)Expedia
From $584 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 $584 per night (USD)VRBO
From $514 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 $514 per night (USD)Expedia
From $595 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 $595 per night (USD)VRBO
From $677 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 $677 per night (USD)Expedia
From $1011 per night (USD)VRBO
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Summary: This is a gorgeous home with in ground *heated* "6 month" pool & "9 month" hot tub - less than a mile walk from ...
From $1011 per night (USD)VRBO
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 $614 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 $614 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 $781 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 $781 per night (USD)VRBO
From $434 per night (USD)Expedia
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 $434 per night (USD)Expedia
From $356 per night (USD)VRBO
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 $356 per night (USD)VRBO
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
Click For PricingVRBO
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 ...
Click For PricingVRBO
From $735 per night (USD)VRBO
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 $735 per night (USD)VRBO
From $490 per night (USD)VRBO
Spacious Good-Value Accommodation! w/ Outdoor Pool, Pet-Friendly
- 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 $490 per night (USD)VRBO
From $189 per night (USD)VRBO
Enjoy a Hassle-Free Stay! Pet-Friendly, Close to William Paca Garden
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Modern family units with private kitchens for the ultimate Annapolis experience This listing is for a room within a hot ...
From $189 per night (USD)VRBO
From $1304 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 $1304 per night (USD)VRBO
From $326 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 $326 per night (USD)Expedia