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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 344 Vacation Homes in Annapolis with updated reviews, rates, and availability.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (215)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Historic Annapolis Home 1.5 blocks from center of town.
Interior

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (35)
"This house was in a fantastic location! It is within walking distance to downtown Annapolis and anything you might need or want. It is a cute little home with all of your needed comforts. "
Historic Annapolis Home 1.5 blocks from center of town.
Book for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Interior

Book for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

2.0 star property
10.0 out of 10, Exceptional, (1)
"We had a great Springtime vacation with kids and a grandparent - our kids enjoyed kayaking and paddle boarding from the doc and gramps was very comfortable watching from the yard. It’s a very convenient location for a family. House was small but had everything we needed and well maintained. We recommend it!!"
Book for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
Fridge, microwave, oven, stovetop

Steps to USNA Gate 3 at historic Gatehouse, on-site parking

2.5 star property
10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in this fabulous property. The location near gate 3 of USNA and the quick walk to downtown made it a perfect spot. The house was impeccably clean, comfortable and roomy. Cathy was exceptionally helpful throughout our booking process and stay. You will absolutely enjoy your stay!"
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
PERFECT LOCATION in the heart of history
Exterior

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (199)
"Great weekend at this property in Annapolis! Location is within walking distance to restaurants and shopping!"
PERFECT LOCATION in the heart of history
7 mins away from Downtown Annapolis
Outdoor dining

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (15)
"A warm and cozy property that can hold that big holiday gathering you want. Well stocked, comfortable, and full of what you need."
7 mins away from Downtown Annapolis
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Fridge, microwave, oven, stovetop

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.8 out of 10, Exceptional, (16)
"Loved the stay, easy and functional for a larger group to get together in Annapolis. "
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Exterior

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (111)
"I visited my midshipman and I couldn’t have asked for a better place! Very comfortable & spacious-yet not too big. It was as if we were home. Location was awesome. Mike was great with immediate communication-especially in preparing us with info well before our check in day! I would definitely stay here again! "
Charming garden row home, easy 4 block walk to the heart of Annapolis.
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (60)
"Great location! Beautifully furnished! I stayed here for a month and loved it. The property manager is awesome. Responds to requests within minutes. Book it you won’t be disappointed!"
Recently Renovated Annapolis Home - Conveniently Located
3-bedroom vacation home in Downtown Annapolis, mins walk to U.S. Naval Academy
Fridge, microwave, oven, stovetop

3-bedroom vacation home in Downtown Annapolis, mins walk to U.S. Naval Academy

9.4 out of 10, Exceptional, (9)
"Thank you Joseph for the great communication and ease of our accommodations. Very clean and quiet. It made our short weekend away so simple and easy!"
The price is AED 808
AED 1,759 total
includes taxes & fees
12 May - 13 May
3-bedroom vacation home in Downtown Annapolis, mins walk to U.S. Naval Academy
Wright's Cottage- Pet's Welcome & EV Charging
Interior

Wright's Cottage- Pet's Welcome & EV Charging

9.8 out of 10, Exceptional, (8)
"Great location. Small but perfect for myself, my daughter & our big goofy dog. Old house but well maintained and cozy, fenced back yard. Really enjoyed our stay!"
The price is AED 386
AED 1,306 total
includes taxes & fees
11 May - 12 May
Wright's Cottage- Pet's Welcome & EV Charging
Newly renovated in DTA w parking
Exterior

Newly renovated in DTA w parking

10.0 out of 10, Exceptional, (1)
"Newly renovated with excellent taste throughout. The location couldn’t have been more convenient. We loved the walk every morning and evening along West St. to Main St. restaurants, bars and shops were all within an easy and enjoyable walk. We had four adults that were very comfortable in the three bedrooms. The main bathroom was spacious and the shower was like you find in a lux hotel. Downstairs bathroom was convenient and well-designed. Basement full bath with shower came in handy when all...
Newly renovated in DTA w parking
Location is perfect and a big bonus we have our own parking at the home!
Smart TV

Location is perfect and a big bonus we have our own parking at the home!

10.0 out of 10, Exceptional, (32)
"The home was cute, clean and conveniently located in downtown Annapolis! Owner was easy to communicate with & stocked with everything you’d need. Would love to stay here again!"
Location is perfect and a big bonus we have our own parking at the home!
2 Mi to Sandy Point State Park: Home w/ Deck!
Fridge, microwave, stovetop, dishwasher

2 Mi to Sandy Point State Park: Home w/ Deck!

8.0 out of 10, Very Good, (2)
"It wes good being that close to the beach"
2 Mi to Sandy Point State Park: Home w/ Deck!
Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House
Terrace/patio

Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House

10.0 out of 10, Exceptional, (41)
"The location of this property is absolutely perfect if you want to be near all the downtown action. Cute street and quiet inside . "
Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Parking

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

10.0 out of 10, Exceptional, (7)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is AED 3,677
AED 5,745 total
includes taxes & fees
11 May - 12 May
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (107)
"Great location. "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Fridge, microwave, oven, stovetop

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (20)
"Great Stay!"
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
USNA Luxury Home, parking, pet friendly
Fridge, microwave, oven, stovetop

USNA Luxury Home, parking, pet friendly

10.0 out of 10, Exceptional, (7)
"Beautiful house in a great location to Main Street Annapolis. "
The price is AED 2,204
AED 4,187 total
includes taxes & fees
12 May - 13 May
USNA Luxury Home, parking, pet friendly
Private Cottage on gated estate
Beach

Private Cottage on gated estate

10.0 out of 10, Exceptional, (22)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Annapolis

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Miscellaneous

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (215)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Parking

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

10.0 out of 10, Exceptional, (7)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is AED 3,677
AED 5,745 total
includes taxes & fees
11 May - 12 May
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Property grounds

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (76)
"Heron house was perfect for our family weekend getaway. Doug and Kris are great hosts and made our stay as easy as could be! "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.