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
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Annapolis vacation homes

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 ￥33,109
￥79,807 total
includes taxes & fees
May 6 - May 7
Charming Pet-Friendly Stay - Near Bay & Beaches.
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 ￥38,362
￥109,331 total
includes taxes & fees
May 6 - May 7
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 ￥30,658
￥80,217 total
includes taxes & fees
May 6 - May 7
Cute bungalow blocks to Stadium
Game room

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

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is ￥35,375
￥63,627 total
includes taxes & fees
May 10 - May 11
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
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 ￥34,385
￥106,858 total
includes taxes & fees
May 6 - May 7
Historic Annapolis Home | 2 Blocks to Main St
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 ￥30,066
￥80,097 total
includes taxes & fees
May 24 - May 25
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
TV

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
The price is ￥23,394
￥91,117 total
includes taxes & fees
May 6 - May 7
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
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, (8 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 ￥45,987
￥90,422 total
includes taxes & fees
May 6 - May 7
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Smart TV, fireplace, foosball, table tennis

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 ￥45,908
￥94,454 total
includes taxes & fees
May 11 - May 12
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 ￥60,530
￥114,708 total
includes taxes & fees
Jun 1 - Jun 2
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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 ￥37,733
￥96,964 total
includes taxes & fees
Jun 1 - Jun 2
Annapolis Retreat - 7 mins from 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 ￥59,491
￥86,613 total
includes taxes & fees
May 6 - May 7
Fabulous 5-bedroom house with AC in charming Annapolis
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 ￥46,318
￥137,286 total
includes taxes & fees
May 6 - May 7
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
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 ￥48,516
￥135,854 total
includes taxes & fees
May 7 - May 8
Stunning 4 BR Home - Walking Distance to Stadium
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 ￥47,103
￥70,702 total
includes taxes & fees
May 10 - May 11
Walk to the stadium! - Lighthouse on Glenwood
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 ￥25,941
￥106,463 total
includes taxes & fees
May 7 - May 8
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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, (77 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is ￥33,960
￥67,929 total
includes taxes & fees
May 26 - May 27
Cozy 2br home w/ parking in downtown Annapolis
Living area

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
Annapolis
The price is ￥38,915
￥100,641 total
includes taxes & fees
May 27 - May 28
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
TV, fireplace, offices

Eastport 4 Bedroom Spacious Gem on Jefferson

Eastport 4 Bedroom Spacious Gem on Jefferson
Eastport
The price is ￥95,313
￥196,361 total
includes taxes & fees
May 6 - May 7
Eastport 4 Bedroom Spacious Gem on Jefferson
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.
The price is ￥46,789
￥76,250 total
includes taxes & fees
May 31 - Jun 1
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
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

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"The hotel was beautiful. The room neat and clean."
Jamise 1-night trip
Posted 2 hours ago
The Westin Annapolis

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
182
Accommodation
294 Vacation Homes
Lowest Price
￥63,627
Highest Price
￥196,361