Holiday Homes in Annapolis

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Annapolis and around

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
4 bedrooms, desk, iron/ironing board, travel cot

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

9.8 out of 10, Exceptional, (7)
"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!"
The price is €477
includes taxes & fees
19 Aug - 20 Aug
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Fisher House: Steps From USNA + Covered Parking!
Fridge, microwave, oven, stovetop

Fisher House: Steps From USNA + Covered Parking!

10.0 out of 10, Exceptional, (11)
"The location is perfect!"
The price is €673
includes taxes & fees
17 Aug - 18 Aug
Fisher House: Steps From USNA + Covered Parking!
Cozy Home in Beautiful Annapolis
Exterior

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
The price is €250
includes taxes & fees
18 Aug - 19 Aug
Cozy Home in Beautiful Annapolis
Annapolis Retreat - 7 mins from downtown Annapolis!
Smart TV, fireplace

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is €510
includes taxes & fees
2 Sept - 3 Sept
Annapolis Retreat - 7 mins from downtown Annapolis!
Mins to DTA - King Beds - Parking
Dining

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!"
Mins to DTA - King Beds - Parking
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Terrace/patio

Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
Pool

Oasis by the Bay - Waterfront Heated Pool Hot Tub!

9.4 out of 10, Exceptional, (3)
"This house is in a prime location. Sweet neighborhood on the Bay. The house itself has a great dock that provides constant activities for kids. The pool was clean and situated with a stunning view. The house has so many sleeping options and can accommodate large groups. The proximity to downtown Annapolis allows for frequent excursions. Property mgt very good. Highly recommend renting!"
The price is €1,080
includes taxes & fees
18 Aug - 19 Aug
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
Cute bungalow blocks to Stadium
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
Cute bungalow blocks to Stadium
Historic Row Home 1 Block from Gate 1 at USNA!
Interior

Historic Row Home 1 Block from Gate 1 at USNA!

10.0 out of 10, Exceptional, (1)
"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. "
The price is €573
includes taxes & fees
18 Aug - 19 Aug
Historic Row Home 1 Block from Gate 1 at USNA!
Naptown Villa House S
Dishwasher, coffee/tea maker, cookware/dishes/utensils

Naptown Villa House S

10.0 out of 10, Exceptional, (1)
"Incredible accomodations at Naptown Villa. Perfect location, beautiful setting, lovely home for the holiday weekend. "
Naptown Villa House S
Cozy 2br home w/ parking in downtown Annapolis
Marina

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (70)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
Cozy 2br home w/ parking in downtown Annapolis
Historic Row Home in Downtown Annapolis
Fridge, microwave, oven, stovetop

Historic Row Home in Downtown Annapolis

The price is €540
includes taxes & fees
20 Aug - 21 Aug
Historic Row Home in Downtown Annapolis
Annapolis Baystone House
TV, fireplace, offices

Annapolis Baystone House

10.0 out of 10, Exceptional, (1)
"The Annapolis bayside house is fully equipped with everything you would need while away from your home. Nicely decorated, clean, high tech features , plenty of games nice bedding, convenient location. It’s a townhouse with three floors so not conducive for elderly people . I would Definately rent this house again"
Annapolis Baystone House
Historic Annapolis Charmer <1Mile to NMC Stadium
6 bedrooms, desk, iron/ironing board, travel cot

Historic Annapolis Charmer <1Mile to NMC Stadium

9.8 out of 10, Exceptional, (6)
"The home was beautiful and spacious. The host was wonderful and communicated with us very well. Would recommended for a large group! "
Historic Annapolis Charmer <1Mile to NMC Stadium
Wright's Cottage- Pet's Welcome & EV Charging
TV, offices

Wright's Cottage- Pet's Welcome & EV Charging

9.0 out of 10, Wonderful, (12)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is €320
includes taxes & fees
2 Sept - 3 Sept
Wright's Cottage- Pet's Welcome & EV Charging
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
Fridge, microwave, oven, stovetop

Spacious 5 BR house - 5 Min Walk to N-MC Stadium!

9.0 out of 10, Wonderful, (2)
"My mom and I visited with 8 grandchildren as part of their Christmas present. We checked out the Naval Academy, monuments in DC, and a football bowl game. The kids enjoyed the new adventures!"
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
Historic 3 BR Home - 15 Min Walk to N-MC Stadium
3 bedrooms, iron/ironing board, WiFi, bed sheets

Historic 3 BR Home - 15 Min Walk to N-MC Stadium

Historic 3 BR Home - 15 Min Walk to N-MC Stadium
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
Fridge, microwave, oven, stovetop

vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy

9.6 out of 10, Exceptional, (13)
"Thank you Joseph for the great communication and ease of our accommodations. Very clean and quiet. It made our short weekend away so simple and easy!"
The price is €363
includes taxes & fees
17 Aug - 18 Aug
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
Annapolis Gem: Stylish and Cozy
Fridge, microwave, oven, stovetop

Annapolis Gem: Stylish and Cozy

The price is €403
includes taxes & fees
14 Sept - 15 Sept
Annapolis Gem: Stylish and Cozy
Charming Annapolis WaterVIEW Home
Outdoor dining

Charming Annapolis WaterVIEW Home

9.6 out of 10, Exceptional, (53)
"This home is a wonderful place to stay. We enjoyed so much about it: the fully-equipped kitchen with spices and every appliance you might need, bathrooms with rain showers/good water pressure, decks for outdoor lounging, plenty of space and nice furnishings in the living room, and a quiet neighborhood that isn't too far away from the downtown area. We would love to come back again!"
Charming Annapolis WaterVIEW Home
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great area and it was a perfect hotel for our trip. "
Lauren 3-night trip
Posted 1 day ago
Graduate by Hilton Annapolis