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Check prices for these dates

Next weekend
18 Apr - 20 Apr
In two weeks
25 Apr - 27 Apr
In one month
9 May - 11 May
In two months
6 Jun - 8 Jun

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!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (211)
"Everything was just as advertised!! Very charming house in a perfect location. Wonderful gas fireplace in the living room, cute back patio, everything we needed and more! This house was absolutely spotless!! A to the cleaning people!! John was a wonderful host! Went out of his way to check on us and offer any assistance if we needed it. We "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Historic Annapolis Home 1.5 blocks from center of town.
Terrace/patio

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (35)
"Great wx and weekend visit to the Naval Academy. Walking distance to everything and neighborhood was a nice getaway from main street "
Historic Annapolis Home 1.5 blocks from center of town.
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Interior

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

2.0 star property
Available 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)
"A great location and plenty of room for visiting groups to be in and out. Clean and well provisioned. Parking was a great feature as well."
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, (196)
"great time"
PERFECT LOCATION in the heart of history
7 mins away from Downtown Annapolis
Fridge, microwave, oven, coffee/tea maker

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (16)
"Loved the house, we were glad to be able to book it on short notice for a large group! Beds were insanely comfortable, and the house had everything we needed. It was clean, comfortable, and a fantastic location. Only downside is that the common areas (living room/kitchen/dining area) are a bit small if you have a larger group (8). Overall a great stay and would stay again!!"
7 mins away from Downtown Annapolis
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
3 bedrooms, iron/ironing board, travel crib, WiFi

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

9.6 out of 10, Exceptional, (15)
"This property is perfect for a weekend getaway. The location is unbeatable, and the house is amazing! Clean, well-appointed and beautiful. The property manager was also wonderful to work with. You won't be disappointed."
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, (109)
"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
Exterior

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (58)
"We had a wonderful stay at this property and would return in the future. Thank you!"
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

9.8 out of 10, Exceptional, (8)
"My sisters and I enjoyed a wonderful weekend in this recently renovated townhouse steps away from downtown - a plus for those of us with cranky knees! Immaculate with crisp comfy beds & linens, two full bathrooms and three bedrooms, we had plenty of room to relax and share a great visit. Smooth check in and check out. Friendly neighbors. Perfect location. relax "
The price is AED 668
AED 1,583 total
includes taxes & fees
13 Apr - 14 Apr
3-bedroom vacation home in Downtown Annapolis, mins walk to U.S. Naval Academy
Wright's Cottage- Pet's Welcome & EV Charging
1 bedroom, iron/ironing board, WiFi, bed sheets

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

9.8 out of 10, Exceptional, (6)
"Great location, cozy cottage, good for dogs, lots to do in and around Annapolis. "
The price is AED 367
AED 1,285 total
includes taxes & fees
21 Apr - 22 Apr
Wright's Cottage- Pet's Welcome & EV Charging
Newly renovated in DTA w parking
Exterior

Newly renovated in DTA w parking

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, (30)
"We had a great long weekend here. The home is very clean with newly updated bathrooms. Having a parking space is a huge advantage and the location is perfect! Close to all of the shops, restaurants and the water. Shari was quick to respond to any questions and was very accommodating. We will definitely 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, (1)
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, (40)
"Everything about this property was perfect. It was clean, comfortable and welcoming. The location couldn’t get much better than this place. We had a great time! "
Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Fridge, microwave, oven, stovetop

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

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 2,578
AED 4,258 total
includes taxes & fees
16 Apr - 17 Apr
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
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)
"Beautifully decorated small house. Very well equipped; complimentary beverage, cheeses and charcuterie tray were a pleasant surprise. Despite being only barely into spring there were lots of flowers blooming in the backyard garden."
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, (17)
"Beautiful and cozy house to spend the weekend-quick walk into town for shopping, cocktails and dining-park your cars (5 spots!) in the driveway and begin your holiday!"
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)
"Stayed here with my boyfriend, brother and sister-in-law while visiting family for Christmas. The property is very spacious, clean, and full of character. We loved the second living area as it allowed us to comfortably spread out. And the location simply can’t be beat. Host was very responsive. Would stay here again!"
The price is AED 1,928
AED 3,827 total
includes taxes & fees
5 May - 6 May
USNA Luxury Home, parking, pet friendly
Private Cottage on gated estate
Property grounds

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!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (211)
"Everything was just as advertised!! Very charming house in a perfect location. Wonderful gas fireplace in the living room, cute back patio, everything we needed and more! This house was absolutely spotless!! A to the cleaning people!! John was a wonderful host! Went out of his way to check on us and offer any assistance if we needed it. We "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Downtown Annapolis Condo w/ Free Parking + Coffee
Property grounds

Downtown Annapolis Condo w/ Free Parking + Coffee

10.0 out of 10, Exceptional, (19)
"Great condominium at a great location. Reserved parking. We were impressed with the owners’ approach—a lot of very nice small details. Beautifully decorated. "
The price is AED 474
AED 1,235 total
includes taxes & fees
29 Apr - 30 Apr
Downtown Annapolis Condo w/ Free Parking + Coffee
Charming Historic Annapolis Home With Two Off-street Parking Places!
Interior

Charming Historic Annapolis Home With Two Off-street Parking Places!

10.0 out of 10, Exceptional, (182)
"A very pleasant place to hang out with family. The road traffic was a little bothersome. "
Charming Historic Annapolis Home With Two Off-street Parking Places!
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.