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
28 Rab. I - 30 Rab. I
In two weeks
4 Rab. II - 6 Rab. II
In one month
18 Rab. II - 20 Rab. II
In two months
16 Jum. I - 18 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!
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 1,428 total
includes taxes & fees
23 Mar - 24 Mar
3-bedroom vacation home in Downtown Annapolis, mins walk to U.S. Naval Academy
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, (105)
"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
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)
"The row house was super cute right off the main road and within walking distance of everything we wanted to do. So many great shops/restaurants in the area. The home is old and quaint. All the beds were very comfortable (and so was the couch) and although we didn't do any cooking there, the kitchen was well stocked. The owners were very responsive to our questions and everything was just as described. It was a little too cold to sit outside but they have a very cute little patio out back. We...
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!!
PERFECT LOCATION in the heart of history
Exterior

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (194)
"Wonderful stay. The home had everything we needed and was very comfortable. Can't beat the location and with 2.5 nice bathrooms and 4 beds everyone was comfortable. Wonderful to have the washer and dryer. Host was very easy to communicate with. It is an old historic house so the stairway is steep if anyone in your party has mobility issues. "
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
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
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
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 2,858
SAR 4,691 total
includes taxes & fees
24 Mar - 25 Mar
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Charming Annapolis WaterVIEW Home
Outdoor dining

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (50)
"This home is a wonderful place to stay. We enjoyed so much about it: the fully-equipped kitchen with spices and every appliance you might need, bathrooms with rain showers/good water pressure, decks for outdoor lounging, plenty of space and nice furnishings in the living room, and a quiet neighborhood that isn't too far away from the downtown area. We would love to come back again!"
Charming Annapolis WaterVIEW Home
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.
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, (73)
"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
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Exterior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

9.2 out of 10, Wonderful, (33)
"Very nice spacious with a beautiful view of the water. Will definitely go back and be prepared to use the available crab pots"
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Fridge, microwave, oven, stovetop

Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!

9.6 out of 10, Exceptional, (106)
"We were in town for a sailing event and the house was in a perfect location for us. "
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Cheerful 3-Bedroom House in Downtown Annapolis
Fridge, microwave, oven, stovetop

Cheerful 3-Bedroom House in Downtown Annapolis

10.0 out of 10, Exceptional, (16)
"Perfect for staying in Annapolis, easy walk to the stadium and to the Academy. Great Restaurants in the area and very walkable location to the rest of Annapolis. Great Amenities in the house and was very clean. Owner is very nice and is a strong communicator "
Cheerful 3-Bedroom House in Downtown Annapolis
Walkable to Main Street at Seashell in the City with 2 parking spots
Point of interest

Walkable to Main Street at Seashell in the City with 2 parking spots

10.0 out of 10, Exceptional, (42)
"We really enjoyed our stay. The location is close to everything you need. Just a walk away. The 2nd floor restrooms were exceptionally nice. Looks like theyve been remodeled recently. I slept like a baby on the comfy bed. Its always appreciated to get a good night sleep. "
Walkable to Main Street at Seashell in the City with 2 parking spots
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
Exterior

Sophisticated Charmer with Parking & Views of the USNA Chapel Dome

9.8 out of 10, Exceptional, (56)
"We came for my husbands 40th reunion. It was the perfect house. Close to everything and so comfy with wonderful bedrooms, kitchen, living quarters and backyard. The parking was also wonderful because there are not a lot of places to park. We had excellent communication. Very quick to reply. Thanks for a great place. I would stay there again and recommend it to anyone."
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
New listing! Stay in the heart of Annapolis on King George Street steps to Gate 1 & Main Street
Fridge, microwave, oven, stovetop

New listing! Stay in the heart of Annapolis on King George Street steps to Gate 1 & Main Street

2.0 star property
New listing! Stay in the heart of Annapolis on King George Street steps to Gate 1 & Main Street
Historic Downtown Union House with Free parking & private patio
Point of interest

Historic Downtown Union House with Free parking & private patio

10.0 out of 10, Exceptional, (25)
"Perfect place to stay for a visit to USNA or Annapolis generally. Property is beautiful and well stocked, and it made for an easy stay "
Historic Downtown Union House with Free parking & private patio
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!
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)
"The row house was super cute right off the main road and within walking distance of everything we wanted to do. So many great shops/restaurants in the area. The home is old and quaint. All the beds were very comfortable (and so was the couch) and although we didn't do any cooking there, the kitchen was well stocked. The owners were very responsive to our questions and everything was just as described. It was a little too cold to sit outside but they have a very cute little patio out back. We...
Historic Annapolis Home 1.5 blocks from center of town.
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.