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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Enjoy serene waterfront views and easy access to moorings and facilities.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (227)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Quiet Relaxing Waterfront Suisse Chalet
Guests gather at the ceremony site, surrounded by lush greenery and a serene water view.

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Enjoy cooking in this well-lit kitchen with a central island, wooden cabinetry, and stainless steel appliances.

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (113)
"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Charming townhome with AC and WiFi in delightful Annapolis
Enjoy cooking in this well-equipped kitchen with a refrigerator, dark wood cabinetry, and a window with blinds.

Charming townhome with AC and WiFi in delightful Annapolis

4.0 out of 10, (1)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
The price is HK$606
HK$870 total
includes taxes & fees
6 Aug - 7 Aug
Charming townhome with AC and WiFi in delightful Annapolis
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Stunning two-story home with a charming entrance, complete with a wreath-adorned door and a cozy porch.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
10.0 out of 10, Exceptional, (24)
"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Cozy Annapolis Cottage
Relax on the outdoor deck surrounded by lush greenery and trees, featuring a sofa set, wicker chair, and small table.

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (13)
"Spent 2 wonderful weeks at this cottage! Very close to walking trail and loop around Naval Stadium. Easy access to shopping dining, highly recommend!!!!"
Cozy Annapolis Cottage
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
Relax by the water's edge, where a row of chairs invites you to unwind and take in the serene views.

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

8.4 out of 10, Very good, (5)
"Relaxing weekend in Annapolis. Enjoyed the quiet and a short walk to the beach"
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.
Charming Historic Annapolis Home With Two Off-street Parking Places!
Staircase leads to a warm and inviting interior with a fireplace and wooden door.

Charming Historic Annapolis Home With Two Off-street Parking Places!

10.0 out of 10, Exceptional, (190)
"A very pleasant place to hang out with family. The road traffic was a little bothersome. "
Charming Historic Annapolis Home With Two Off-street Parking Places!
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Stroll up to the charming entrance, where a brick pathway leads to a cozy home with a red door and inviting porch.

Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking

9.8 out of 10, Exceptional, (45)
"Great location to the academy and shopping"
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Enjoy a room with a sliding glass door leading to a balcony offering a water view.

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

9.8 out of 10, Exceptional, (17)
"We wanted to celebrate Easter with our two daughters who go to Loyola in Baltimore so we decided to stay in Annapolis area. We absolutely loved the house. The location and view was amazing- right on the Chesapeake bay! The house was clean and welcoming. There were so many nice little touches that made us feel welcomed. We had a great weekend celebrating Easter with our two daughters and son. The house was the perfect size for the 5 of us. "
Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view
Historic Annapolis Home 1.5 blocks from center of town.
Stroll through the charming outdoor corridor to a cozy patio area with comfortable seating and a scenic view.

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (39)
"Perfect accommodations for girls weekend. Close to everything, very walkable. "
Historic Annapolis Home 1.5 blocks from center of town.
Walk to USNA, Main St w Parking Historic Wisteria
Step into a historic building with a preserved facade, featuring a traditional entrance with a brass handle and a glimpse into the interior.

Walk to USNA, Main St w Parking Historic Wisteria

9.8 out of 10, Exceptional, (61)
"Amazing location and unique VRBO!!!!!!!"
Walk to USNA, Main St w Parking Historic Wisteria
Recently Renovated Annapolis Home - Conveniently Located
Enjoy cooking in this well-equipped kitchen with a central island, gas stove, and ample counter space.

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (64)
"House is beautiful and in a great location! "
Recently Renovated Annapolis Home - Conveniently Located
Stunning 4 BR Home - Walking Distance to Stadium
Enjoy cooking in this well-equipped kitchen with a central island and bar stools, featuring a stove, oven, and refrigerator.

Stunning 4 BR Home - Walking Distance to Stadium

The price is HK$1,217
HK$5,181 total
includes taxes & fees
6 Aug - 7 Aug
Stunning 4 BR Home - Walking Distance to Stadium
Chesapeake Comfort, Annapolis.
Enjoy outdoor seating on the porch with a set of chairs and a table.

Chesapeake Comfort, Annapolis.

10.0 out of 10, Exceptional, (17)
"Perfect weekend getaway with friends and our pups. Easy walk to downtown Annapolis. The host was very responsive. "
The price is HK$3,988
HK$6,908 total
includes taxes & fees
8 Aug - 9 Aug
Chesapeake Comfort, Annapolis.
Eastport Cottage .5 mi from Downtown Annapolis
Stunning two-story home with a central entrance, flanked by windows, set amidst a beautifully manicured lawn and lush gardens.

Eastport Cottage .5 mi from Downtown Annapolis

10.0 out of 10, Exceptional, (53)
"Terrific house and good location"
Eastport Cottage .5 mi from Downtown Annapolis
Timeless Charm Meets Modern Comfort
Fridge, microwave, oven, stovetop

Timeless Charm Meets Modern Comfort

10.0 out of 10, Exceptional, (1)
"We enjoyed being in walking distance of everything we needed for the stay, restaurants, shopping, marina, and history. "
Timeless Charm Meets Modern Comfort
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Relax on the porch with a comfortable chair and small table, surrounded by a beautifully landscaped garden.

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."
The price is HK$3,532
HK$6,389 total
includes taxes & fees
1 Sept - 2 Sept
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis
Relax on the covered porch with a wicker sofa, glass coffee table, and potted plant, surrounded by large windows offering a view of the trees.

Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis

9.8 out of 10, Exceptional, (31)
"The property was very nice. It felt so homey. Clean and nicely appointed, even decorated for Christmas! In 2 short days ther was so much laughter and memories made! We would definitely recommend this home for a family stay!and memories made!"
Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown 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.
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Top Annapolis Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"The only issue was no clean up or fresh towels for the second night "
James 2-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis