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Compare 289 Vacation Homes in Annapolis with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (208)
"We loved our stay here! The location is unbeatable and having access to parking was very convenient. The house itself was quaint with character and very clean! My husband and I stayed with our 4 young children and had ample space. The beds were all comfy and the kitchen had everything we needed. Communication with the host was great! We really hope to stay here again in the future! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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

10.0 out of 10, Exceptional, (104)
"Great location. "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Historic Home with Parking Steps From Capital & USNA

9.6 out of 10, Exceptional, (9)
"What a cute, historic row house that is about five or six houses down from the Maryland State house and a few blocks up from the docks and the Naval Academy entrance. The bonus is there is a parking space--just leave your car and walk to all of downtown Annapolis. Bathroom & kitchen are practically brand new. Very clean, very comfortable, and allowed us to wander the shops, museums, and food around town. "
Historic Home with Parking Steps From Capital & USNA

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

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.

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

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

MODERN 2022 NEWLY BUILT TOWNHOME

10.0 out of 10, Exceptional, (9)
"This place was perfect for out boat show week!"
MODERN 2022 NEWLY BUILT TOWNHOME

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

Luxury Waterfront Executive Family Home Annapolis with All Amenities

Luxury Waterfront Executive Family Home Annapolis with All Amenities

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

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

Historic Annapolis Home 1.5 blocks from center of town.

10.0 out of 10, Exceptional, (34)
"Perfect accommodations for girls weekend. Close to everything, very walkable. "
Historic Annapolis Home 1.5 blocks from center of town.

6 Mi to Dtwn: Family-Friendly Home in Annapolis!

9.4 out of 10, Exceptional, (3)
"We were in Annapolis for our Midshipman’s birthday. There was plenty of room to have friends over for dinner. The house was clean , kitchen well stocked, and our college kids had fun playing the games provided. The proximity to The Yard was very nice. We all enjoyed our stay. "
6 Mi to Dtwn: Family-Friendly Home in Annapolis!

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (6)
"We're in the process of selling our home and used this place as our home away from home while the listing went live. It was cozy and had everything that we needed to feel like we could rest up after the difficult process of prepping our house. And a safe, fenced in yard for our dogs. It was perfect, thank you! "
Cozy Annapolis Cottage

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

9.2 out of 10, Wonderful, (32)
"We immensely enjoyed our stay! The home is a peaceful retreat yet close enough to Annapolis and DC to visit! It was super clean! It was a joy to sit outside and watch the wildlife on the water during the day! Will definitely come back!"
Waterfront Annapolis Home: Fire Pit & Fishing Pier

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

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

9.6 out of 10, Exceptional, (8)
"House was very nice- loved the roof top. Beds very comfy and decor was nice. Neighborhood was diverse. Kimberly was wonderful. "
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

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
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!

10.0 out of 10, Exceptional, (208)
"We loved our stay here! The location is unbeatable and having access to parking was very convenient. The house itself was quaint with character and very clean! My husband and I stayed with our 4 young children and had ample space. The beds were all comfy and the kitchen had everything we needed. Communication with the host was great! We really hope to stay here again in the future! "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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.

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

10.0 out of 10, Exceptional, (104)
"Great location. "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
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.