Search Vacation Homes in Annapolis

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Annapolis holiday 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 HK$1,350
HK$3,797 total
includes taxes & fees
14 Apr - 15 Apr
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Living area

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
The price is HK$1,190
HK$4,580 total
includes taxes & fees
14 Apr - 15 Apr
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
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, (13 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is HK$2,255
HK$4,660 total
includes taxes & fees
21 Apr - 22 Apr
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Marina

Historic Annapolis Home | 2 Blocks to Main St

Historic Annapolis Home | 2 Blocks to Main St
Historic District
10.0 out of 10, Exceptional, (16 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is HK$1,558
HK$5,124 total
includes taxes & fees
19 Apr - 20 Apr
Historic Annapolis Home | 2 Blocks to Main St
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$1,175
HK$4,428 total
includes taxes & fees
19 Apr - 20 Apr
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
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)
"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.
The price is HK$2,709
HK$5,312 total
includes taxes & fees
21 Apr - 22 Apr
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Living area

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
Annapolis
The price is HK$1,689
HK$4,693 total
includes taxes & fees
27 Apr - 28 Apr
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
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$1,402
HK$4,223 total
includes taxes & fees
27 Apr - 28 Apr
Annapolis Retreat - 7 mins from downtown 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)
"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$2,291
HK$4,504 total
includes taxes & fees
14 Apr - 15 Apr
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
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$1,613
HK$4,112 total
includes taxes & fees
20 Apr - 21 Apr
Cute bungalow blocks to Stadium
Dining

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is HK$1,822
HK$4,353 total
includes taxes & fees
3 May - 4 May
Charming Pet-Friendly Stay - Near Bay & Beaches.
Exterior

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful house & our hosts were very responsive to our questions. We had a wonderful experience!"
United States
JP Y.
The price is HK$1,958
HK$6,383 total
includes taxes & fees
14 Apr - 15 Apr
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Games room

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

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is HK$1,762
HK$3,196 total
includes taxes & fees
10 May - 11 May
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
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.
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$1,727
HK$3,986 total
includes taxes & fees
14 Apr - 15 Apr
Mins to DTA - King Beds - 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, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
The price is HK$1,159
HK$2,705 total
includes taxes & fees
5 May - 6 May
Cozy 2br home w/ parking in downtown Annapolis
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 HK$2,514
HK$6,892 total
includes taxes & fees
14 Apr - 15 Apr
Stunning 4 BR Home - Walking Distance 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)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is HK$1,980
HK$3,052 total
includes taxes & fees
20 Apr - 21 Apr
Fabulous 5-bedroom house with AC in charming Annapolis
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)
"Wonderful time, very thoughtful touches throughout. "
United States
Glori V.
The price is HK$2,067
HK$3,160 total
includes taxes & fees
3 May - 4 May
Walk to the stadium! - Lighthouse on Glenwood
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 HK$2,240
HK$4,642 total
includes taxes & fees
14 Apr - 15 Apr
Chesapeake Comfort, 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Annapolis Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Valet parking while convenient did not arrive on time on the day of the marathon and nearly ended being late for the start line:( the staff barely acknowledged the miss. "
Uday 2-night trip
Posted 7 hours ago
Historic Inns of Annapolis

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
188
Accommodation
269 Vacation Homes
Lowest Price
HK$2,705
Highest Price
HK$6,892

Explore a world of travel with Expedia