Annapolis Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

Our top choices for Annapolis vacation homes

Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
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 CA $236
CA $660 total
includes taxes & fees
Mar 8 - Mar 9
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
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
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is CA $326
CA $733 total
includes taxes & fees
Mar 17 - Mar 18
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
TV, offices

Wright's Cottage- Pet's Welcome & EV Charging

Wright's Cottage- Pet's Welcome & EV Charging
Annapolis
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is CA $235
CA $500 total
includes taxes & fees
Mar 9 - Mar 10
Wright's Cottage- Pet's Welcome & EV Charging
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
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 CA $217
CA $708 total
includes taxes & fees
Mar 12 - Mar 13
Annapolis Retreat - 7 mins from downtown Annapolis!
Fridge, microwave, oven, stovetop

Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard
Cape Saint Claire
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 CA $205
CA $764 total
includes taxes & fees
Mar 5 - Mar 6
Neptune by the Water - Pet Friendly Fenced Yard
Smart TV, fireplace, foosball, table tennis

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

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
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.
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Microwave, oven, stovetop, dishwasher

Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
9.8 out of 10, Exceptional, (8 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 CA $342
CA $532 total
includes taxes & fees
Mar 8 - Mar 9
Walk to the stadium! - Lighthouse on Glenwood
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
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 CA $193
CA $699 total
includes taxes & fees
Mar 5 - Mar 6
Cute bungalow blocks to Stadium
Microwave, oven, stovetop, dishwasher

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
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 CA $394
CA $600 total
includes taxes & fees
Mar 8 - Mar 9
Fabulous 5-bedroom house with AC in charming Annapolis
Property grounds

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
9.2 out of 10, Wonderful, (5 reviews)
The price is CA $400
CA $790 total
includes taxes & fees
Mar 5 - Mar 6
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Interior

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

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
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 CA $193
CA $967 total
includes taxes & fees
Mar 5 - Mar 6
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Fridge, microwave, oven, stovetop

All Star Annapolis Retreat - Walk to Stadium

All Star Annapolis Retreat - Walk to Stadium
Admiral Heights
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 CA $342
CA $1,112 total
includes taxes & fees
Mar 8 - Mar 9
All Star Annapolis Retreat - Walk to Stadium
Fridge, microwave, oven, stovetop

Stunning 4 BR Home - Walking Distance to Stadium

Stunning 4 BR Home - Walking Distance to Stadium
Homewood
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 CA $284
CA $1,169 total
includes taxes & fees
Mar 5 - Mar 6
Stunning 4 BR Home - Walking Distance to Stadium
Game room

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is CA $273
CA $514 total
includes taxes & fees
Mar 22 - Mar 23
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Terrace/patio

Chesapeake Comfort, Annapolis.

Chesapeake Comfort, Annapolis.
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 CA $313
CA $712 total
includes taxes & fees
Mar 5 - Mar 6
Chesapeake Comfort, Annapolis.
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, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is CA $183
CA $451 total
includes taxes & fees
Mar 24 - Mar 25
Cozy 2br home w/ parking in downtown Annapolis

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
Annapolis
The price is CA $276
CA $713 total
includes taxes & fees
Mar 25 - Mar 26
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
Marina

Fisher House: Steps From USNA + Covered Parking!

Fisher House: Steps From USNA + Covered Parking!
Historic District
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 CA $342
CA $981 total
includes taxes & fees
Mar 9 - Mar 10
Fisher House: Steps From USNA + Covered Parking!
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
9.4 out of 10, Exceptional, (20 reviews)
"Great place, excellent location!"
United States
Joseph C.
The price is CA $1,130
CA $1,930 total
includes taxes & fees
Mar 9 - Mar 10
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Fridge, microwave, oven, stovetop

Mins to DTA - King Beds - Parking

Mins to DTA - King Beds - Parking
Annapolis
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 CA $382
CA $801 total
includes taxes & fees
Mar 5 - Mar 6
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Was at Governor Calvert House. Beautiful historic building that is well maintained. Room was clean and comfortable. Parking is minimal, and valet parking is quite expensive, with "dynamic pricing". Hotel is walking distance to many shops and restaurants. Staff was pleasant and accommodating. "
E Wayne 1-night trip
Posted 10 hours ago
Historic Inns of Annapolis

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
214
Accommodation
294 Vacation Homes
Lowest Price
CA $451
Highest Price
CA $1,930

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