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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Annapolis vacation homes

Interior

Vacation Home in Hillsmere

Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is ￥26,722
￥84,360 total
includes taxes & fees
Jan 20 - Jan 21
Annapolis Retreat - 7 mins from downtown Annapolis!
Smart TV, fireplace, foosball, table tennis

Vacation Home in Homewood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (8 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is ￥31,308
￥76,790 total
includes taxes & fees
Jan 20 - Jan 21
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Marina

Vacation Home in Annapolis

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is ￥27,250
￥76,670 total
includes taxes & fees
Jan 20 - Jan 21
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Fridge, microwave, oven, stovetop

Vacation Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is ￥26,406
￥92,652 total
includes taxes & fees
Jan 20 - Jan 21
Neptune by the Water - Pet Friendly Fenced Yard
Fridge, microwave, oven, stovetop

Vacation Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is ￥27,039
￥88,004 total
includes taxes & fees
Jan 20 - Jan 21
Cute bungalow blocks to Stadium
Property grounds

Vacation Home in Cape Saint Claire

Cozy Winter Annapolis Escape, Near Downtown, Firepit + Bar, Sleeps 12, Parking
2.0 star property
9.0 out of 10, Wonderful, (4 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 ￥42,550
￥87,443 total
includes taxes & fees
Jan 20 - Jan 21
Cozy Winter Annapolis Escape, Near Downtown, Firepit + Bar, Sleeps 12, Parking
Game room

Vacation Home in Eastport

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
The price is ￥26,090
￥52,635 total
includes taxes & fees
Jan 20 - Jan 21
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Interior

Vacation Home in Historic District

Historic Row Home | Hot Tub - 1 Block from Gate 1!
10.0 out of 10, Exceptional, (5 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 ￥25,141
￥116,987 total
includes taxes & fees
Jan 20 - Jan 21
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Beach nearby, sun loungers, beach towels

Vacation Home in Arundel on the Bay

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is ￥33,442
￥79,403 total
includes taxes & fees
Feb 2 - Feb 3
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Marina

Vacation Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (73 reviews)
"Great location!"
United States
Burton S.
The price is ￥19,133
￥49,391 total
includes taxes & fees
Jan 20 - Jan 21
Cozy 2br home w/ parking in downtown Annapolis
Microwave, oven, stovetop, dishwasher

Vacation Home in Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is ￥57,492
￥85,190 total
includes taxes & fees
Jan 20 - Jan 21
Fabulous 5-bedroom house with AC in charming Annapolis
Fridge, microwave, oven, stovetop

Vacation Home in Admiral Heights

All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (8 reviews)
"Great house, perfect for Navy football game"
United States
Kathy N.
The price is ￥39,530
￥122,935 total
includes taxes & fees
Jan 20 - Jan 21
All Star Annapolis Retreat - Walk to Stadium
Marina

Vacation Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (14 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is ￥52,180
￥129,785 total
includes taxes & fees
Feb 2 - Feb 3
Fisher House: Steps From USNA + Covered Parking!
Microwave, oven, stovetop, dishwasher

Vacation Home in Annapolis

Walk to the stadium! - Lighthouse on Glenwood
9.8 out of 10, Exceptional, (7 reviews)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
United States
Tom D.
The price is ￥39,530
￥61,828 total
includes taxes & fees
Jan 20 - Jan 21
Walk to the stadium! - Lighthouse on Glenwood
Fridge, microwave, oven, stovetop

Vacation Home in Homewood

Stunning 4 BR Home - Walking Distance to Stadium
10.0 out of 10, Exceptional, (2 reviews)
"This house was a TEN! We booked it for family and friends to stay with us for a military retirement over homecoming weekend. The location was great. Perfect for walking to and from the stadium with kids. Easy few minutes drive or Uber to the Academy. The house was well equipped and perfect for a big group. The yard was amazing! Wish we’d planned on a family flag football game! Plenty of space in the kitchen and living room. Management was super responsive when we needed something or had a...
United States
Catherine S.
The price is ￥38,581
￥144,746 total
includes taxes & fees
Jan 25 - Jan 26
Stunning 4 BR Home - Walking Distance to Stadium
Marina

Vacation Home in Murray Hill

Naptown Villa House-Walkable Downtown 5BR, parking
10.0 out of 10, Exceptional, (6 reviews)
"The house was fantastic! Beautifully maintained, clean, ample parking, great location to downtown, and has everything you’d need for a getaway!"
United States
Heather U.
The price is ￥70,284
￥144,475 total
includes taxes & fees
Jan 20 - Jan 21
Naptown Villa House-Walkable Downtown 5BR, parking
Exterior

Vacation Home in Historic District

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
9.4 out of 10, Exceptional, (20 reviews)
"Great place, excellent location!"
United States
Joseph C.
The price is ￥113,214
￥200,986 total
includes taxes & fees
Jan 26 - Jan 27
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Smart TV, fireplace, foosball, table tennis

Vacation Home in Homewood

Historic Annapolis Charmer <1Mile to NMC Stadium
9.8 out of 10, Exceptional, (6 reviews)
"The home was beautiful and spacious. The host was wonderful and communicated with us very well. Would recommended for a large group! "
United States
Kathlyn F.
The price is ￥112,898
￥219,012 total
includes taxes & fees
Feb 17 - Feb 18
Historic Annapolis Charmer <1Mile to NMC Stadium
Exterior

Vacation Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is ￥10,075
￥38,167 total
includes taxes & fees
Jan 20 - Jan 21
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Exterior

Vacation Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32 reviews)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is ￥11,954
￥40,327 total
includes taxes & fees
Jan 21 - Jan 22
Charming Coastal/Country Home w/3 Acres & Sauna!
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Staff was very nice "
anthony 1-night trip
Posted 19 hours ago
Graduate by Hilton Annapolis

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
242
Accommodation
294 Vacation Homes
Lowest Price
￥38,167
Highest Price
￥219,012