Holiday Homes in Annapolis

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Check prices for these dates

In two weeks
19 June - 21 June
In two months
31 July - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Annapolis holiday homes

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 AU$832
includes taxes & fees
2 June - 3 June
Annapolis Retreat - 7 mins from downtown Annapolis!
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, (14 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AU$947
includes taxes & fees
2 June - 3 June
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is AU$810
includes taxes & fees
9 June - 10 June
Charming Annapolis WaterVIEW Home
Smart TV, fireplace, table football, ping pong

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 AU$834
includes taxes & fees
8 June - 9 June
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
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is AU$996
includes taxes & fees
4 June - 5 June
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
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
9.6 out of 10, Exceptional, (11 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.
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
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, (79 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
Cozy 2br home w/ parking in downtown Annapolis
Microwave, oven, stovetop, dishwasher

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.6 out of 10, Excellent, (4 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is AU$774
includes taxes & fees
8 June - 9 June
Fabulous 5-bedroom house with AC in charming Annapolis
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 AU$735
includes taxes & fees
8 June - 9 June
Cute bungalow blocks to Stadium
Terrace/patio

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Annapolis
10.0 out of 10, Exceptional, (21 reviews)
"In Annapolis for youth sports. Great place to stay. "
United States
jason S.
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
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 AU$710
includes taxes & fees
15 June - 16 June
Chapel Gate 3BR Steps to City Dock & Naval Academy
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.
Chesapeake Comfort, Annapolis.
Fridge, microwave, oven, stovetop

Mins to DTA - King Beds - Parking

Mins to DTA - King Beds - Parking
Annapolis
10.0 out of 10, Exceptional, (5 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 AU$932
includes taxes & fees
14 June - 15 June
Mins to DTA - King Beds - Parking
Smart TV, fireplace, table football, ping pong

Historic Annapolis Charmer <1Mile to NMC Stadium

Historic Annapolis Charmer <1Mile to NMC Stadium
Homewood
9.8 out of 10, Exceptional, (7 reviews)
"The house was well equipped, clean and comfortable. The host was very accommodating and responsive. This is a great home if you have a large crowd and so convenient to historic Annapolis. "
United States
Susan R.
The price is AU$2,098
includes taxes & fees
15 June - 16 June
Historic Annapolis Charmer <1Mile to NMC Stadium
Interior

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

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.8 out of 10, Exceptional, (6 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 AU$1,291
includes taxes & fees
14 June - 15 June
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Exterior detail

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is AU$749
includes taxes & fees
2 June - 3 June
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Exterior detail

Admiral's Abode - Charming Retreat

Admiral's Abode - Charming Retreat
Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Great location, well appointed home and good communication."
United States
Andrea K.
Admiral's Abode - Charming Retreat
Exterior

Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
The price is AU$890
includes taxes & fees
8 June - 9 June
Adorable home steps from Navy stadium!
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 AU$1,125
includes taxes & fees
14 June - 15 June
Eastport 3 bedroom Cottage: Walk to Downtown
Smart TV, books

Beautiful Historic Flat next to City Dock + USNA

Beautiful Historic Flat next to City Dock + USNA
Historic District
10.0 out of 10, Exceptional, (3 reviews)
"We had the best time- thank you for a great stay! Megan's place was beautifully appointed and in the perfect location for our needs. She was super responsive to messages and accommodating to an early check-in. I would definitely stay here again! "
United States
Johnnie B.
The price is AU$1,229
includes taxes & fees
7 June - 8 June
Beautiful Historic Flat next to City Dock + USNA
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

6/10 Okay
"The room and staff were fine and no problems. Whoever designed the bathrooms should be fired. they only offer cleaning for towels every 3 days but there are no towel racks to hang wet towels in the bathroom. It was extremely small and you actually had to step to the side of the toilet to close the door. Really disappointed overall with the stay because of this."
DAVID 2-night trip
Posted 6 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

Find out more about Annapolis

Annapolis Holiday Homes information

Number of reviews
259
Accommodation
295 Holiday Homes
Lowest Price
AU$656
Highest Price
AU$2,007