A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Annapolis vacation homes

Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is ￥31,851
￥93,448 total
includes taxes & fees
Jul 21 - Jul 22
Historic Row Home in Downtown Annapolis
Outdoor dining

Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
The price is ￥34,923
￥85,771 total
includes taxes & fees
Jul 15 - Jul 16
Chapel Gate 3BR Steps to City Dock & Naval Academy
Living area

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is ￥40,028
￥102,485 total
includes taxes & fees
Aug 11 - Aug 12
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Microwave, oven, stovetop, dishwasher

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.4 out of 10, Very Good, (6 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is ￥63,892
￥93,208 total
includes taxes & fees
Jul 20 - Jul 21
Fabulous 5-bedroom house with AC in charming Annapolis
Property grounds

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.0 out of 10, Wonderful, (14 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is ￥62,137
￥113,801 total
includes taxes & fees
Jul 15 - Jul 16
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Exterior

Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
The price is ￥62,915
￥102,467 total
includes taxes & fees
Jul 16 - Jul 17
Adorable home steps from Navy stadium!
Beach nearby, sun loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (16 reviews)
"Very nice property with plenty of room and a nice outdoor space. The hot tub was a great bonus. Close enough to visit USNA but the location feels like a vacation spot!"
United States
Gail S.
The price is ￥60,675
￥116,023 total
includes taxes & fees
Jul 22 - Jul 23
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Fridge, microwave, oven, stovetop

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is ￥51,334
￥129,375 total
includes taxes & fees
Jul 28 - Jul 29
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is ￥77,606
￥140,816 total
includes taxes & fees
Jul 21 - Jul 22
Charming Annapolis WaterVIEW Home
Smart TV, fireplace, foosball, table tennis

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is ￥64,330
￥120,931 total
includes taxes & fees
Jul 21 - Jul 22
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Fridge, microwave, oven, stovetop

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is ￥54,324
￥131,785 total
includes taxes & fees
Aug 3 - Aug 4
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ￥36,551
￥97,226 total
includes taxes & fees
Aug 12 - Aug 13
Annapolis Retreat - 7 mins from downtown Annapolis!
Coffee/tea maker, fridge, microwave, oven

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"House is perfect for weekend get away with family. Walking distance to everything. "
United States
Nathan A.
The price is ￥70,533
￥142,633 total
includes taxes & fees
Jul 15 - Jul 16
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Exterior

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
9.2 out of 10, Wonderful, (25 reviews)
"Our group really enjoyed the large outdoor area on the side of the house. We were part of a larger group in town for a wedding and we were able to host a get together for a fairly large group. Over all the house was very comfortable with a great location near heart of Annapolis."
United States
Paul
The price is ￥185,206
￥322,621 total
includes taxes & fees
Jul 19 - Jul 20
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is ￥34,115
￥86,642 total
includes taxes & fees
Jul 22 - Jul 23
Cute bungalow blocks to Stadium
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (82 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is ￥46,887
￥84,232 total
includes taxes & fees
Aug 10 - Aug 11
Cozy 2br home w/ parking in downtown Annapolis
Marina

Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront
Historic District
10.0 out of 10, Exceptional, (1 review)
The price is ￥107,379
￥192,785 total
includes taxes & fees
Jul 15 - Jul 16
Historic Downtown Luxury • USNA • Waterfront
Fridge, microwave, oven, stovetop

Eastport 3 bedroom Cottage: Walk to Downtown

Eastport 3 bedroom Cottage: Walk to Downtown
Eastport
10.0 out of 10, Exceptional, (1 review)
"We had a nice stay. All was fine."
United States
william c.
The price is ￥55,451
￥125,069 total
includes taxes & fees
Jul 15 - Jul 16
Eastport 3 bedroom Cottage: Walk to Downtown
Exterior detail

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
8.8 out of 10, Excellent, (8 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is ￥44,999
￥108,523 total
includes taxes & fees
Jul 28 - Jul 29
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Coffee/tea maker, fridge, microwave, oven

Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (6 reviews)
"Very recent remodel, and all top notch. You can tell the owners put their heart and soul into this property. All the rooms have been very nicely done. Bathrooms were beautifully done. Beds were comfortable. The area is very peaceful and quiet. We really enjoyed the back yard space also. Sat at patio table and used grill. Large TV’s everywhere! We were able to sit at patio table, grill some burgers and watch Final Four games from TV in kitchen area. If you have a Midshipman, this property is...
United States
Brian S.
The price is ￥35,089
￥208,712 total
includes taxes & fees
Jul 22 - Jul 23
Luxe Row Home Steps to USNA Gate 3!
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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Top Annapolis Hotel Reviews

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

8/10 Good
"Overall, my stay at the Courtyard by Marriott in Annapolis had several strong positives, but also a few maintenance and safety concerns that should be addressed. The room was very clean, and the bed was extremely comfortable — both the mattress and pillows made for a great night’s sleep. Breakfast at the Bistro was delicious, and the staff throughout the hotel were friendly and welcoming. I also enjoyed the pool area, which was clean and pleasant. That said, there were some issues that took away from the experience. I cut my finger on a broken elevator button, which definitely needs repair. The whirlpool jets were not working, so it functioned more like a hot tub than an actual whirlpool. More concerning, several of the side exit doors appeared to be broken: guests could enter from the outside, but could not exit from the inside. This was inconvenient, but more importantly, it seems like a potential fire code and safety issue. With some attention to maintenance and safety, this could be a much better stay. The staff, cleanliness, comfortable room, breakfast, and pool area were all highlights, but the hotel should prioritize fixing the broken doors, elevator button, and whirlpool jets."
Michelle 2-night trip
Posted less than an hour ago
Courtyard by Marriott Annapolis

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