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Vacation Homes in Friendship

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (24)
"I love this property and host! Incredible place to stay close to museums the Naval Academy, local shopping, excellent restaurants and the airport. I will highly recommend this property to friends & family. "
Charming Historic Townhouse Steps From USNA

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!

The Cozy Crab- Your Charming Haven in Lovely North Beach!

9.4 out of 10, Exceptional, (3)
"We had a great time! The house was really nice, very comfortable and clean. It had everything that you needed. I really liked that everything was controlled by alexa even the window blinds. I definitely recommend staying here and I definitely will be returning. "
The Cozy Crab- Your Charming Haven in Lovely North Beach!

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!

10.0 out of 10, Exceptional, (112)
"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!

The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

9.6 out of 10, Exceptional, (24)
"Was the perfect spot for a nice weekend getaway with some friends."
The Private Pool is OPEN with Bay Views & Steps from The Kentmorr Beach Bar and Grill

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (11)
"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

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

9.4 out of 10, Exceptional, (13)
"Wonderful location and just perfect for our family! "
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

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.

Rising Sun Bay View Cottage

Rising Sun Bay View Cottage

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

10.0 out of 10, Exceptional, (187)
"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

10.0 out of 10, Exceptional, (44)
"This was the perfect place for my group to stay while visiting for the Army Navy weekend. We had 6 adults and 2 teens and the location within walking distance of both downtown and the Yard were ideal for everyone to sightsee. The house was clean and well maintained, and the first floor (living room/bar/kitchen) made a great place for the group to gather and cook meals. I’d definitely recommend this him and stay here again. "
Modern Elegance in Historic Annapolis Just One Block to Gate 1 w Parking

Spacious 4 Bedroom Home w/ Hot Tub

9.8 out of 10, Exceptional, (19)
"We had a wonderful experience with our latest stay. They were flexible on arrival time, beds were very comfortable and the house was very comfortable! Will definitely stay again!"
The price is AED 694
AED 2,017 total
includes taxes & fees
23 Jul - 24 Jul
Spacious 4 Bedroom Home w/ Hot Tub

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (38)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AED 459
AED 1,218 total
includes taxes & fees
23 Jul - 24 Jul
Relax on Kent Island in 3 Bedroom Home w/Waterview

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (64)
"The property was well- maintained and the kitchen was well-equipped for our needs. Short walk to North Beach for dining and Boardwalk strolls. Nice and toasty for our winter stay - really enjoyed the trip."
The Blue Crab Beach House - Free beach passes

Bayfront Maryland Retreat w/ Deck, Near Beaches!

9.8 out of 10, Exceptional, (9)
"Lovely, serene, comfortable, waterfront home. Conveniently close to the essentials, restaurants, pier, beach, markets, and more. "
Bayfront Maryland Retreat w/ Deck, Near Beaches!

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

10.0 out of 10, Exceptional, (119)
"Clean and spacious. Great views! Loved the beach! Found a bunch of fossils. Enjoyed kayaking. Overall outstanding!"
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Pet-Friendly Annapolis Home: Walk to Beach!

9.2 out of 10, Wonderful, (13)
"Great neighborhood, relaxing proorrty with alot of outdoor seating"
Pet-Friendly Annapolis Home: Walk to Beach!

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

Stunning 4 BR Home - Walking Distance to Stadium

The price is AED 599
AED 2,479 total
includes taxes & fees
21 Jul - 22 Jul
Stunning 4 BR Home - Walking Distance to Stadium
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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