Search Vacation Homes in Annapolis

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
4 Rab. II - 6 Rab. II
In two weeks
11 Rab. II - 13 Rab. II
In one month
25 Rab. II - 27 Rab. II
In two months
23 Jum. I - 25 Jum. I

Compare 342 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, (209)
"Perfect Location - Easy Process - Comfortable Home!"
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.

10.0 out of 10, Exceptional, (34)
"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.
Your Annapolis Adventure Starts Here!!
Fridge, microwave, oven, stovetop

Your Annapolis Adventure Starts Here!!

10.0 out of 10, Exceptional, (138)
"We enjoyed our stay as much as the 1st time. Great spot for an Annapolis getaway! House is comfortable and location is ideal. Gracious and responsive host."
Your Annapolis Adventure Starts Here!!
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, (194)
"Lovely home steps from the naval academy. More than enough room for our family of 4. There was a storm the night before we arrived that resulted in a partial power outage. Once we notified them, both the owner and property manager responded promptly and were very accommodating. The rest of our stay was comfortable and enjoyable. Highly recommend for the historic Annapolis experience!"
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, (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
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (14)
"The house was very clean and super comfortable. We didn’t cook anything during our stay but the kitchen looked well stocked. Beds were comfortable. The location was awesome. Very short walk to downtown and just steps to the Naval Academy visitors entrance. We very much enjoyed our stayed!"
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
Fridge, microwave, oven, stovetop

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 SAR 548
SAR 1,441 total
includes taxes & fees
30 Mar - 31 Mar
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

10.0 out of 10, Exceptional, (4)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is SAR 375
SAR 1,317 total
includes taxes & fees
31 Mar - 1 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, (29)
"."
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, (39)
"Great house. We comfortably fit 8 adults (two family celebration). Property manager was responsive. The bar was an added bonus- so much fun and we were amazed by the glassware available. Parking also a major bonus for downtown Annapolis. We’ve already rebooked for next year."
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
Parking

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 SAR 2,637
SAR 4,358 total
includes taxes & fees
31 Mar - 1 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, (106)
"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 SAR 2,007
SAR 3,908 total
includes taxes & fees
31 Mar - 1 Apr
USNA Luxury Home, parking, pet friendly
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.
Don't see what you're looking for?
See all available properties in Annapolis
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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, (209)
"Perfect Location - Easy Process - Comfortable Home!"
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. "
Downtown Annapolis Condo w/ Free Parking + Coffee
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Exterior

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
10.0 out of 10, Exceptional, (15)
"First time in Annapolis to watch East Carolina win the Military Bowl and tour the Naval Academy.Great location, cute, clean, and comfortable place in a fun town with lots of great restaurants and bars."
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
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.