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Compare 280 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, (207)
"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!

Freshly renovated 3-story home 1 block from USNA!

9.8 out of 10, Exceptional, (31)
"What a perfect house in a central location to all things walkable in Downtown Annapolis. House had everything we needed, was comfortable and clean. "
The price is AED 635
AED 2,500 total
includes taxes & fees
5 Mar - 6 Mar
Freshly renovated 3-story home 1 block from USNA!

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

Walk to Lake & Boat Ramp: Central Gem in Annapolis

Walk to Lake & Boat Ramp: Central Gem in Annapolis

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

Brand New Spacious Luxury Home

10.0 out of 10, Exceptional, (5)
"This home was exactly as described. Very clean, comfortable and well equipped. This home was beautifully designed, well furnished and had everything we need to enjoy a short friends getaway. Thank you for a wonderful stay. "
Brand New Spacious Luxury Home

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

Serene waterfront sunsets in this sprawling historic Annapolis home

9.6 out of 10, Exceptional, (28)
"Gorgeous neighborhood and a very cool house. The view is amazing and the sunsets were incredible. The house could have been cleaner, there were stains on some of the furniture, and the kitchen was a mess -- we had to wash every pot or pan before using it and the cabinets above the stove were grimy. There was only 1 dish towel in the house. Most of the towels and sheets were pretty old and threadbare and needed to be replaced. Overall very good but not 5 star which is what they are striving...
Serene waterfront sunsets in this sprawling historic Annapolis home

Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

9.8 out of 10, Exceptional, (9)
"This was a perfect home away from home for four adults and two children, ages 5 and 7. The children loved the loft area and named it the "Kids Zone." The pool and the massive amount of toys were a big hit too. Lots of towels, kitchen equipment, beautiful bed linens, outdoor and indoor spaces made this a wonderful vacation home. While the waterfront was beautiful the front porch was our favorite spot in the morning, Just lovely."
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D

Pet-Friendly Annapolis Home: Walk to Beach!

10.0 out of 10, Exceptional, (6)
"Property is very well maintained and you feel at home. Proximity of the little park is perfect for young kids. Street very quiet. Parking space is great. We had a great family time and we will be back when weather is warmer to enjoy access to the beach."
Pet-Friendly Annapolis Home: Walk to Beach!

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (24)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

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!

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"The property was very nice. It felt so homey. Clean and nicely appointed, even decorated for Christmas! In 2 short days ther was so much laughter and memories made! We would definitely recommend this home for a family stay!and memories made!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

Historic Annapolis Home 1.5 blocks from center of town.

10.0 out of 10, Exceptional, (33)
"Perfect accommodations for girls weekend. Close to everything, very walkable. "
Historic Annapolis Home 1.5 blocks from center of town.

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.

Jackson's Bunker in Eastport with fenced-in backyard

9.8 out of 10, Exceptional, (9)
"We were just minutes away from all the good restaurants, shops, sights, and harbor. Safe area. Place as described, but no nightstands by any of the beds. One room had a closet and no drawers, the other drawers and no closets. Manager responded immediately to any questions. Great customer service. We would stay there again."
Jackson's Bunker in Eastport with fenced-in backyard

Charming brick home with patio, WiFi, AC, & W/D - walk to everything

9.0 out of 10, Wonderful, (22)
"We had a lovely time in Annapolis. The house was clean and comfy. I would recommend it. Just make sure you have a small car as the parking area is very tight. Our VW Jetta fit okay, but it was not much room to get out."
Charming brick home with patio, WiFi, AC, & W/D - walk to everything

La Maison - Stunning waterfront views with pool

10.0 out of 10, Exceptional, (94)
"Our family thoroughly enjoyed our stay. The house is beautiful with great views and convenient location to Annapolis and surrounding areas. Very clean and well kept property with all the amenities needed. Host is very attentive and checks in to make sure your check-in and time there goes smoothly. Great host! Thank you for sharing your home. We hope to return in warmer weather. "
La Maison - Stunning waterfront views with pool

Captain's Quarters - Eastport!

9.2 out of 10, Wonderful, (7)
"Nice place but dated if that matters. Clean, comfortable, host was very helpful. Convenient to downtown. We also went to close by Sandy point to see the Lights on the bay. We reccomend a better door offering more privacy in downsatairs bath."
The price is AED 914
AED 2,388 total
includes taxes & fees
9 Mar - 10 Mar
Captain's Quarters - Eastport!
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, (207)
"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!

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 536
AED 1,403 total
includes taxes & fees
5 Mar - 6 Mar
3-bedroom vacation home in Downtown Annapolis, mins walk to U.S. Naval Academy
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.