Search Vacation Homes in Friendship

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 558 Vacation Homes in Friendship with updated reviews, rates, and availability.

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

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

10.0 out of 10, Exceptional, (218)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Parking

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

10.0 out of 10, Exceptional, (7)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is AED 3,276
AED 5,226 total
includes taxes & fees
9 Jun - 10 Jun
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Edgewater/Mayo Getaway!
Fridge, microwave, oven, stovetop

Edgewater/Mayo Getaway!

9.8 out of 10, Exceptional, (17)
"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 1,959 total
includes taxes & fees
1 Jun - 2 Jun
Edgewater/Mayo Getaway!
The Blue Crab Beach House - Free beach passes
Miscellaneous

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (57)
"Everything close by!"
The Blue Crab Beach House - Free beach passes
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Property grounds

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.6 out of 10, Exceptional, (78)
"This is a great location The house is clean and updated. We enjoyed and would stay here again."
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Property grounds

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (78)
"Heron house was perfect for our family weekend getaway. Doug and Kris are great hosts and made our stay as easy as could be! "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (35)
"Owner was very welcoming and left a bottle of wine as a nice gesture. Excellent communication."
The price is AED 328
AED 1,044 total
includes taxes & fees
2 Jun - 3 Jun
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (5)
"Our stay at the house was great. The host had amazing customer service and the location is beautiful."
The price is AED 716
AED 1,398 total
includes taxes & fees
2 Jun - 3 Jun
The Cottage
The Lazy Crab Beach House - Free beach passes
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (50)
"Would stay again."
The Lazy Crab Beach House - Free beach passes
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Beach nearby

Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants

10.0 out of 10, Exceptional, (25)
"Everything about our stay was wonderful..the hosts were so quick to respond to any questions amd were very patient with me with all of my questions..I would DEFINITELY stay here again!!"
The price is AED 569
AED 1,737 total
includes taxes & fees
2 Jun - 3 Jun
Huge Beach Bungalow w/Yard, Beach Passes, 2 King Bds near Boardwalk, Restaurants
Charming townhome with AC and WiFi in delightful Annapolis
Microwave, coffee/tea maker, paper towels

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 "
Charming townhome with AC and WiFi in delightful Annapolis
Wright's Cottage- Pet's Welcome & EV Charging
Interior

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

9.6 out of 10, Exceptional, (10)
"Great location. Small but perfect for myself, my daughter & our big goofy dog. Old house but well maintained and cozy, fenced back yard. Really enjoyed our stay!"
The price is AED 441
AED 1,382 total
includes taxes & fees
9 Jun - 10 Jun
Wright's Cottage- Pet's Welcome & EV Charging
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Exterior

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

2.5 star property
10.0 out of 10, Exceptional, (18)
"First time in Annapolis to watch East Carolina win the Military Bowl and tour the Naval Academy.Great location, cute, clean, and comfortable place in a fun town with lots of great restaurants and bars."
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
South County Poolside Hangout
Pool

South County Poolside Hangout

8.0 out of 10, Very Good, (1)
"First off I want to say the house was absolutely beautiful. The pictures does it no Justice. The house was very clean, and well equipped with everything you can think you’ll possibly need. The beds are comfortable, the area is nice, and the land is beautiful. Carolyn was very, very responsive. Everything I messaged her about she responded right back. The only down fall was that I booked the home mainly for the pool, but the pool was dirty due to a storm prior to my stay. Carolyn tried to get...
South County Poolside Hangout
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (61)
"We had a wonderful stay at this property and would return in the future. Thank you!"
Recently Renovated Annapolis Home - Conveniently Located
Historic Annapolis Home 1.5 blocks from center of town.
Interior

Historic Annapolis Home 1.5 blocks from center of town.

9.8 out of 10, Exceptional, (35)
"Perfect accommodations for girls weekend. Close to everything, very walkable. "
Historic Annapolis Home 1.5 blocks from center of town.
Sweet Gumball Cottage North Beach MD Free Beach Pass!
Beach towels

Sweet Gumball Cottage North Beach MD Free Beach Pass!

2.0 star property
9.6 out of 10, Exceptional, (5)
"The property was super nice, equipped with all that was needed and also very organized and clean. The location was perfect, walking distance to the board, restaurants and the beach. The owner was very responsive and flexible. We came as a family to celebrate my birthday and we had a wonderful time! Thank you 💕"
Sweet Gumball Cottage North Beach MD Free Beach Pass!
Location is perfect and a big bonus we have our own parking at the home!
Smart TV

Location is perfect and a big bonus we have our own parking at the home!

10.0 out of 10, Exceptional, (33)
"The home was cute, clean and conveniently located in downtown Annapolis! Owner was easy to communicate with & stocked with everything you’d need. Would love to stay here again!"
Location is perfect and a big bonus we have our own parking at the home!
Waterfront Cheerful 6 BR Home with Private Pier
Smart TV, fireplace, video games, offices

Waterfront Cheerful 6 BR Home with Private Pier

9.8 out of 10, Exceptional, (33)
"The property was clean and comfy. Our group of 11 were very comfortable in this beautiful house "
Waterfront Cheerful 6 BR Home with Private Pier
Beach Home with King Bed and Beach Passes in a Cute Town
Miscellaneous

Beach Home with King Bed and Beach Passes in a Cute Town

10.0 out of 10, Exceptional, (11)
"Excellent"
The price is AED 558
AED 1,497 total
includes taxes & fees
9 Jun - 10 Jun
Beach Home with King Bed and Beach Passes in a Cute Town
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free