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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 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 HK$1,528
HK$4,387 total
includes taxes & fees
8 Jun - 9 Jun
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 HK$2,109
HK$4,611 total
includes taxes & fees
8 Jun - 9 Jun
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 HK$2,194
HK$4,637 total
includes taxes & fees
8 Jun - 9 Jun
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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 HK$2,856
HK$5,463 total
includes taxes & fees
10 Jun - 11 Jun
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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 HK$1,340
HK$3,759 total
includes taxes & fees
3 Jun - 4 Jun
Chapel Gate 3BR Steps to City Dock & Naval Academy
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 HK$3,075
HK$4,453 total
includes taxes & fees
8 Jun - 9 Jun
Fabulous 5-bedroom house with AC in charming Annapolis
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 HK$2,069
HK$5,656 total
includes taxes & fees
15 Jun - 16 Jun
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
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 HK$1,677
HK$4,240 total
includes taxes & fees
8 Jun - 9 Jun
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, (80 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is HK$1,802
HK$3,556 total
includes taxes & fees
10 Jun - 11 Jun
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.
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 HK$1,756
HK$5,915 total
includes taxes & fees
8 Jun - 9 Jun
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 HK$4,506
HK$7,657 total
includes taxes & fees
28 Jun - 29 Jun
Mins to DTA - King Beds - Parking
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 HK$3,043
HK$6,515 total
includes taxes & fees
3 Jun - 4 Jun
Eastport 3 bedroom Cottage: Walk to Downtown
Exterior

Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
The price is HK$3,476
HK$5,552 total
includes taxes & fees
7 Jun - 8 Jun
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.
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 HK$1,722
HK$4,232 total
includes taxes & fees
3 Jun - 4 Jun
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
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 HK$3,900
HK$7,529 total
includes taxes & fees
3 Jun - 4 Jun
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 HK$3,919
HK$7,040 total
includes taxes & fees
7 Jun - 8 Jun
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 HK$3,519
HK$8,156 total
includes taxes & fees
11 Jun - 12 Jun
Two Historic Rowhomes in Downtown Annapolis
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
9.0 out of 10, Wonderful, (24 reviews)
"The owners were very good with pre and post-check in communications, and were on site to meet us and show us the property. It was an excellent stay with an excellent location. Kitchen was well stocked and lots of room for everyone."
United States
Ward U.
The price is HK$8,018
HK$14,367 total
includes taxes & fees
8 Jun - 9 Jun
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
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

8/10 Good
"The room was very clean and beautifully appointed. The only problem for me is that the hotel is near the highway and a Main Street. The traffic is So loud. Woke me up every early, it was still dark outside. Add to that the sound of the air conditioning unit going on and off. The last night I just turned it to fan only. Thankfully it was not too hot outside. Unfortunately I couldn’t turn down the sound of the heavy trucks rolling by."
Jacqueline 2-night trip
Posted 3 hours ago
Crowne Plaza Annapolis by IHG

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
249
Accommodation
287 Vacation Homes
Lowest Price
HK$3,556
Highest Price
HK$14,367

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