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$811
includes taxes & fees
8 June - 9 June
Annapolis Retreat - 7 mins from downtown Annapolis!
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$825
includes taxes & fees
8 June - 9 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
Living area

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
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
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$802
includes taxes & fees
15 June - 16 June
Fabulous 5-bedroom house with AC in charming 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 AU$656
includes taxes & fees
2 June - 3 June
Chapel Gate 3BR Steps to City Dock & Naval Academy
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$774
includes taxes & fees
15 June - 16 June
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, (79 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
Cozy 2br home w/ parking in downtown Annapolis
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$1,880
includes taxes & fees
8 June - 9 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$1,074
includes taxes & fees
8 June - 9 June
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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
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!
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.
The price is AU$1,712
includes taxes & fees
18 June - 19 June
Admiral's Abode - Charming Retreat
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
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$1,139
includes taxes & fees
2 June - 3 June
Eastport 3 bedroom Cottage: Walk to Downtown
Fridge, microwave, oven, stovetop

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic District
10.0 out of 10, Exceptional, (6 reviews)
"The property was in wonderful condition and had true Annapolis charm! The kitchen was fully stocked with everything we needed. The location could not be beat, it was walking distance to everything! The host was very communicative and responded very quickly to any questions. It was a fantastic stay! "
United States
Mary Elizabeth M.
The price is AU$1,315
includes taxes & fees
2 June - 3 June
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
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
Shower, hair dryer, shampoo

Two Historic Rowhomes in Downtown Annapolis

Two Historic Rowhomes in Downtown Annapolis
Historic District
The price is AU$1,399
includes taxes & fees
11 June - 12 June
Two Historic Rowhomes in Downtown Annapolis
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

6/10 Okay
"Breakfast not worth the money ,hot tub unusable "
Loren 2-night trip
Posted 1 hour ago
Crowne Plaza Annapolis by IHG

Find out more about Annapolis

Annapolis Holiday Homes information

Number of reviews
224
Accommodation
295 Holiday Homes
Lowest Price
AU$656
Highest Price
AU$1,880