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Check prices for these dates

In two weeks
Mar 13 - Mar 15
In two months
Apr 24 - Apr 26
In three months
May 22 - May 24
In four months
Jun 19 - Jun 21

Our top choices for Annapolis vacation homes

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 ￥26,894
￥75,667 total
includes taxes & fees
Mar 3 - Mar 4
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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 ￥35,813
￥82,277 total
includes taxes & fees
Mar 3 - Mar 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
TV, offices

Vacation Home in Annapolis

Wright's Cottage- Pet's Welcome & EV Charging
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is ￥25,786
￥55,724 total
includes taxes & fees
Mar 9 - Mar 10
Wright's Cottage- Pet's Welcome & EV Charging
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 ￥24,812
￥81,121 total
includes taxes & fees
Mar 3 - Mar 4
Annapolis Retreat - 7 mins from downtown Annapolis!
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)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
The price is ￥24,656
￥89,126 total
includes taxes & fees
Mar 5 - Mar 6
Neptune by the Water - Pet Friendly Fenced Yard
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, (9 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 ￥36,984
￥83,790 total
includes taxes & fees
Mar 3 - Mar 4
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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 ￥39,013
￥61,019 total
includes taxes & fees
Mar 3 - Mar 4
Walk to the stadium! - Lighthouse on Glenwood
Fridge, microwave, oven, stovetop

Vacation Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is ￥23,251
￥81,692 total
includes taxes & fees
Mar 5 - Mar 6
Cute bungalow blocks to Stadium
Microwave, oven, stovetop, dishwasher

Vacation Home in Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
8.0 out of 10, Very Good, (3 reviews)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is ￥44,942
￥68,668 total
includes taxes & fees
Mar 9 - Mar 10
Fabulous 5-bedroom house with AC in charming Annapolis
Property grounds

Vacation Home in Cape Saint Claire

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
9.2 out of 10, Wonderful, (5 reviews)
The price is ￥45,645
￥90,995 total
includes taxes & fees
Mar 3 - Mar 4
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
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 ￥22,003
￥111,897 total
includes taxes & fees
Mar 3 - Mar 4
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Fridge, microwave, oven, stovetop

Vacation Home in Admiral Heights

All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house & our hosts were very responsive to our questions. We had a wonderful experience!"
United States
JP Y.
The price is ￥39,013
￥123,283 total
includes taxes & fees
Mar 3 - Mar 4
All Star Annapolis Retreat - Walk to Stadium
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 ￥38,076
￥142,851 total
includes taxes & fees
Mar 3 - Mar 4
Stunning 4 BR Home - Walking Distance to Stadium
Game room

Vacation Home in Eastport

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
The price is ￥31,210
￥59,062 total
includes taxes & fees
Mar 22 - Mar 23
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Terrace/patio

Vacation Home in Annapolis

Chesapeake Comfort, Annapolis.
9.8 out of 10, Exceptional, (20 reviews)
"Great location, nice space, great backyard to hang out with dogs. "
United States
Stephanie M.
The price is ￥35,735
￥82,188 total
includes taxes & fees
Mar 3 - Mar 4
Chesapeake Comfort, Annapolis.
Marina

Vacation Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is ￥25,124
￥54,792 total
includes taxes & fees
Mar 31 - Apr 1
Cozy 2br home w/ parking in downtown Annapolis

Vacation Home in Annapolis

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
The price is ￥31,460
￥81,763 total
includes taxes & fees
Mar 8 - Mar 9
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
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 ￥48,063
￥123,638 total
includes taxes & fees
Mar 9 - Mar 10
Fisher House: Steps From USNA + Covered 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 ￥128,897
￥220,770 total
includes taxes & fees
Mar 9 - Mar 10
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Fridge, microwave, oven, stovetop

Vacation Home in Annapolis

Mins to DTA - King Beds - Parking
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful home with very attentive host. Great place for family getaway. Will definitely be back! Go Navy."
United States
Nader E.
The price is ￥38,232
￥85,390 total
includes taxes & fees
Mar 31 - Apr 1
Mins to DTA - King Beds - 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.
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Top Annapolis Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Elevator was out but we were able to stay on the main level. Stay was good. Breakfast was ok. "
Nathan 2-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Annapolis, MD

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
208
Accommodation
294 Vacation Homes
Lowest Price
￥54,792
Highest Price
￥220,770