A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Annapolis holiday homes

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, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$2,929
HK$5,601 total
includes taxes & fees
22 Jul - 23 Jul
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Fridge, microwave, oven, stovetop

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is HK$1,898
HK$5,435 total
includes taxes & fees
10 Jul - 11 Jul
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
9.0 out of 10, Wonderful, (14 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.
The price is HK$3,352
HK$5,950 total
includes taxes & fees
13 Jul - 14 Jul
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Outdoor dining

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (72 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is HK$3,763
HK$6,828 total
includes taxes & fees
13 Jul - 14 Jul
Charming Annapolis WaterVIEW Home
Microwave, oven, stovetop, dishwasher

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.4 out of 10, Very good, (6 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is HK$3,204
HK$4,645 total
includes taxes & fees
12 Jul - 13 Jul
Fabulous 5-bedroom house with AC in charming Annapolis
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$2,462
HK$4,988 total
includes taxes & fees
13 Jul - 14 Jul
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Fridge, microwave, oven, stovetop

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
The price is HK$2,298
HK$6,015 total
includes taxes & fees
13 Jul - 14 Jul
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
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$1,961
HK$4,962 total
includes taxes & fees
22 Jul - 23 Jul
Annapolis Retreat - 7 mins from downtown Annapolis!
Exterior

Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
Adorable home steps from Navy stadium!
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
9.2 out of 10, Wonderful, (24 reviews)
"Great place, excellent location!"
United States
Joseph C.
The price is HK$9,136
HK$15,833 total
includes taxes & fees
15 Jul - 16 Jul
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
TV, offices

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is HK$1,521
HK$4,524 total
includes taxes & fees
13 Jul - 14 Jul
Historic Row Home in Downtown Annapolis
Living area

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is HK$2,134
HK$5,339 total
includes taxes & fees
4 Aug - 5 Aug
Cozy 3BR Annapolis sleeps 6 Private Deck, 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.
Historic Annapolis Charmer <1Mile to NMC Stadium
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$1,694
HK$4,205 total
includes taxes & fees
13 Jul - 14 Jul
Chapel Gate 3BR Steps to City Dock & Naval Academy
Marina

Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront
Historic District
10.0 out of 10, Exceptional, (1 review)
Historic Downtown Luxury • USNA • Waterfront
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, (7 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$3,731
HK$7,311 total
includes taxes & fees
13 Jul - 14 Jul
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is HK$1,757
HK$4,299 total
includes taxes & fees
22 Jul - 23 Jul
Cute bungalow blocks to 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 HK$2,922
HK$6,362 total
includes taxes & fees
14 Jul - 15 Jul
Eastport 3 bedroom Cottage: Walk to Downtown
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$3,333
HK$6,133 total
includes taxes & fees
27 Jul - 28 Jul
Mins to DTA - King Beds - Parking
Interior

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

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
8.8 out of 10, Excellent, (8 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$2,596
HK$5,766 total
includes taxes & fees
17 Jul - 18 Jul
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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
"Other than the very comfortable beds, the best thing about our stay here is the location. It's an easy 10 minutes walk to the wharf, market space, USNA, state capital, etc. The rooms were very clean and the valet staff was super fast."
Shelley 2-night trip
Posted 3 hours ago
Historic Inns of Annapolis

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
181
Accommodation
288 Vacation Homes
Lowest Price
HK$4,205
Highest Price
HK$15,833

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