Search Vacation Homes in Annapolis

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Nov 14 - Nov 16
In two weeks
Nov 21 - Nov 23
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Dec 5 - Dec 7
In two months
Jan 2 - Jan 4

Vacation Homes in Annapolis

Terrace/patio
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
$392 nightly
The price is $447
Nov 4 - Nov 5
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium
Cute bungalow blocks to Stadium
10.0 out of 10, Exceptional, (5)
"We had a great stay in this property. The inside looks just like the pictures and feels like it was newly renovated. The kitchen and baths were spectacular. The location was great, it is less than 1/4 mile to the USNA Marine Corps Stadium and also has great access to West Street and all that has to offer. It's a nice quiet neighborhood, jogging trail right in front of the house, close to shopping and dining. The beds and linens were fresh and comfortable. The open floor plan layout...
United States
Tim G.
$468 nightly
The price is $529
Nov 4 - Nov 5
Total with taxes and fees
Cute bungalow blocks to Stadium
Microwave, oven, stovetop, dishwasher
Annapolis Retreat - 7 mins from downtown Annapolis!
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (4)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$464 nightly
The price is $529
Nov 4 - Nov 5
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
Marina
Cozy 2br home w/ parking in downtown Annapolis
Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (71)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
$268 nightly
The price is $306
Nov 4 - Nov 5
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
4 bedrooms, desk, iron/ironing board, travel crib
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
$443 nightly
The price is $505
Nov 5 - Nov 6
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard
Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
$468 nightly
The price is $497
Nov 4 - Nov 5
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
3 bedrooms, iron/ironing board, travel crib, WiFi
★ Midcentury Modern Getaway ★ Prime Location ★
★ Midcentury Modern Getaway ★ Prime Location ★
10.0 out of 10, Exceptional, (35)
"This place is super cute and Ryan was very accommodating which made my life much simpler :) The location is perfect for walking around Downtown Annapolis and onto the Academy. We would definitely stay here again."
United States
Elizabeth B.
$483 nightly
The price is $550
Nov 4 - Nov 5
Total with taxes and fees
★ Midcentury Modern Getaway ★ Prime Location ★
Dining
Mins to DTA - King Beds - Parking
Mins to DTA - King Beds - Parking
2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
United States
Holly W.
$454 nightly
The price is $518
Nov 4 - Nov 5
Total with taxes and fees
Mins to DTA - King Beds - Parking
Fridge, microwave, oven, stovetop
Fisher House: Steps From USNA + Covered Parking!
Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (13)
"There were four adults and a dog in our party. The house was clean, comfortable, and well stocked. Perfect location to enjoy Annapolis for the 4th of July weekend! Everything is an easy walk. Parking at the Hillman Garage was easy and just steps away. We especially enjoyed the back yard and appreciated the large table with umbrella to shade us from the sun for barbecuing and games. The B4K team helpful and responsive, and their webpage made check-in and check-out easy. "
United States
Michael L.
$583 nightly
The price is $627
Nov 4 - Nov 5
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!
Fridge, microwave, oven, stovetop
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
9.4 out of 10, Exceptional, (15)
"Limited living room seating for family of 5"
United States
Christine C.
$372 nightly
The price is $424
Nov 5 - Nov 6
Total with taxes and fees
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
TV, offices
Wright's Cottage- Pet's Welcome & EV Charging
Wright's Cottage- Pet's Welcome & EV Charging
9.2 out of 10, Wonderful, (15)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
United States
Fr. Jamie C.
$340 nightly
The price is $388
Dec 3 - Dec 4
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging
Terrace/patio
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
$312 nightly
The price is $356
Nov 4 - Nov 5
Total with taxes and fees
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Interior
Historic Row Home 1 Block from Gate 1 at USNA!
Historic Row Home 1 Block from Gate 1 at USNA!
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
$639 nightly
The price is $728
Nov 11 - Nov 12
Total with taxes and fees
Historic Row Home 1 Block from Gate 1 at USNA!
Fridge, microwave, oven, stovetop
Historic Row Home in Downtown Annapolis
Historic Row Home in Downtown Annapolis
$614 nightly
The price is $700
Nov 4 - Nov 5
Total with taxes and fees
Historic Row Home in Downtown Annapolis
Microwave, oven, stovetop, dishwasher
Walk to the stadium! - Lighthouse on Glenwood
Walk to the stadium! - Lighthouse on Glenwood
10.0 out of 10, Exceptional, (2)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
United States
Tom D.
$284 nightly
The price is $324
Nov 4 - Nov 5
Total with taxes and fees
Walk to the stadium! - Lighthouse on Glenwood
Fridge, microwave, oven, stovetop
All Star Annapolis Retreat - Walk to Stadium
All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (6)
"Everything was high end and clean. The location was great- very close to navy stadium and in walking distance to a few restaurants (.5 -1 mile).Thank you for a great stay!"
United States
Susanne G.
$622 nightly
The price is $662
Nov 4 - Nov 5
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium
Terrace/patio
Chesapeake Comfort, Annapolis.
Chesapeake Comfort, Annapolis.
9.8 out of 10, Exceptional, (18)
"Perfect weekend getaway with friends and our pups. Easy walk to downtown Annapolis. The host was very responsive. "
United States
Diane L.
$437 nightly
The price is $498
Nov 10 - Nov 11
Total with taxes and fees
Chesapeake Comfort, Annapolis.
Fridge, microwave, oven, stovetop
Stunning 4 BR Home - Walking Distance to Stadium
Stunning 4 BR Home - Walking Distance to Stadium
$782 nightly
The price is $891
Nov 10 - Nov 11
Total with taxes and fees
Stunning 4 BR Home - Walking Distance to Stadium
Interior
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly
10.0 out of 10, Exceptional, (28)
"We only had a short stay but the communication with Justin was extremely quick and responsive - very clear and a great host. The property was really clean, welcoming and perfect for our short break. "
United States
Lee B.
$685 nightly
The price is $781
Nov 25 - Nov 26
Total with taxes and fees
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly
TV, fireplace, offices
Annapolis Baystone House
Annapolis Baystone House
10.0 out of 10, Exceptional, (3)
"Good stay at a solid property. The trundle beds were a welcome surprise in two of the bedrooms. I would include those in the listing as they helped get everyone into beds for the stay. Nice place. Good value. "
United States
David D.
$656 nightly
The price is $748
Nov 16 - Nov 17
Total with taxes and fees
Annapolis Baystone House
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Staff was very friendly answering all questions, room was clean and very comfortable bed"
Frances 1-night trip
Posted 8 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
226
Accommodation
314 Vacation Homes
Lowest Price
$306
Highest Price
$891

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