Friendship Vacation Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
Apr 19 - Apr 20
Tomorrow
Apr 20 - Apr 21
Next weekend
Apr 25 - Apr 27
In two weeks
May 2 - May 4

Vacation Rentals in Friendship

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (212)
"The house was absolutely perfect for our USNA Reunion. About 10 steps to Gate 1 and just a few more to the heart of downtown made it a weekend we will remember. The host was responsive and accommodated our requests and was very kind. I would definitely stay here again."
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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, (74)
"Nothing like home away from home!! Very comfortable home. Thank you. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
Chesapeake Houseboat Getaway on Kent Island, Maryland
Smart TV, fireplace

Chesapeake Houseboat Getaway on Kent Island, Maryland

9.8 out of 10, Exceptional, (25)
"Rainy weather limited activities but would return to property"
Chesapeake Houseboat Getaway on Kent Island, Maryland
The Blue Crab Beach House - Free beach passes
Fridge, microwave, oven, stovetop

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (52)
"Cute as a button. Very, very clean, kitchen has everything, living room very comfortable for us 4 adults. Fenced yard was perfect for our furry companion. Excellent location-quiet neighborhood, easy walk to beach and restaurants.Host is very prompt responding to any inquiry. You won’t regret this rental!!"
The Blue Crab Beach House - Free beach passes
Downtown Annapolis Condo w/ Free Parking + Coffee
Property grounds

Downtown Annapolis Condo w/ Free Parking + Coffee

10.0 out of 10, Exceptional, (19)
"Great condominium at a great location. Reserved parking. We were impressed with the owners’ approach—a lot of very nice small details. Beautifully decorated. "
The price is CA $151
CA $420 total
includes taxes & fees
Apr 29 - Apr 30
Downtown Annapolis Condo w/ Free Parking + Coffee
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Fridge, microwave, oven, stovetop

Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock

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 CA $994
CA $1,633 total
includes taxes & fees
Apr 23 - Apr 24
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Exterior

Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (39)
"This place is great. From the layout, to the sauna, screened in porch and backyard, the owners have thought hard about what features make for a luxurious, comfortable and fun experience. They were also very helpful with all aspects of the process - booking, arrival times, access to the home, help with what to do while there. "
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is CA $270
CA $530 total
includes taxes & fees
Apr 28 - Apr 29
The Cottage
Relax on Kent Island in 3 Bedroom Home w/Waterview
Smart TV

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (34)
"Clean, Spacious, and exactly as advertised! "
The price is CA $97
CA $341 total
includes taxes & fees
Apr 20 - Apr 21
Relax on Kent Island in 3 Bedroom Home w/Waterview
Romantic Two Bedroom Condo
Fridge, microwave, oven, stovetop

Romantic Two Bedroom Condo

10.0 out of 10, Exceptional, (71)
"Nice little two bedroom with everything you need. Food is conveniently close. If simple is what you are looking for this fits."
Romantic Two Bedroom Condo
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Property grounds

Rockhold Creek Cottage, Water Front, Vacation Home, Docks

9.8 out of 10, Exceptional, (88)
"Ritchie, our host was extremely accommodating. Home looked exactly like the pictures. Very clean and comfortable. Water front! Many good restaurants within walking distance."
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
The Lazy Crab Beach House - Free beach passes
Exterior

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (46)
"Exactly as described. Appreciated coffee & cream upon arrival too."
The Lazy Crab Beach House - Free beach passes
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Terrace/patio

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (174)
"The Navy cabin was just as pictured/described and Brett was a pleasure to deal with. The views were spectacular and we greatly enjoyed exploring the small beaches nearby. A day trip to Solomon‘s capped off our stay. Would love to go back and enjoy the serene nature of this rental."
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (207)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Outdoor pool

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (43)
"Quiet and tranquil. Nicely decorated and will definitely stay here again when we return to the area. "
The price is CA $221
CA $430 total
includes taxes & fees
Apr 20 - Apr 21
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Interior

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

10.0 out of 10, Exceptional, (113)
"This place was a wonderful spot for our family to have a long weekend getaway. It's on a bluff right next to the ocean with a glorious view and a stairway access to the beach. The beds are comfortable, the house has lots of great spaces to relax or play games, and the beach is a wonderful space to explore, find seashells and possibly a fossil sharks tooth (we had no luck there, but we did find a whale vertebrae, so that's something!). But in any event, we highly recommend! "
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
3 bedrooms, iron/ironing board, travel crib, WiFi

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.6 out of 10, Exceptional, (15)
"This property is perfect for a weekend getaway. The location is unbeatable, and the house is amazing! Clean, well-appointed and beautiful. The property manager was also wonderful to work with. You won't be disappointed."
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Modern Waterfront House with amazing views of the ChesapeakeBay!
Fridge, microwave, oven, stovetop

Modern Waterfront House with amazing views of the ChesapeakeBay!

Modern Waterfront House with amazing views of the ChesapeakeBay!
Cozy Cottage with access to and partially obstructed views of the bay.
Fridge, microwave, oven, stovetop

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.
Family Beach House: Spacious Deck, Grill & Views
Pool

Family Beach House: Spacious Deck, Grill & Views

9.6 out of 10, Exceptional, (4)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
The price is CA $269
CA $640 total
includes taxes & fees
May 20 - May 21
Family Beach House: Spacious Deck, Grill & Views
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.
Don't see what you're looking for?
See all available properties in Friendship
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Friendship you may be interested in

Historic Inns of Annapolis
Exterior

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1738)
"Attentive! Clean, well decorated. Perfect location"
The price is CA $234
CA $314 total
includes taxes & fees
Apr 20 - Apr 21
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Exterior

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

3.0 star property
6.2 out of 10, (1567)
"Staff was very friendly. The only downfall was the elevator. One was broken and the other was kinda sketchy and suuuuper slow. "
The price is CA $121
CA $138 total
includes taxes & fees
Apr 20 - Apr 21
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Country Inn & Suites by Radisson, Annapolis, MD
Hypo-allergenic bedding, desk, blackout drapes, iron/ironing board

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Seemed safe and the room was quiet. Easy parking right in front. Shower was good, clean and comfy. Nice grill pub ‘Lures’ just down the street."
The price is CA $128
CA $146 total
includes taxes & fees
May 1 - May 2
Country Inn & Suites by Radisson, Annapolis, MD
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.

Frequently asked questions

Can I find vacation rentals in Friendship?

Yes, we give you a choice of vacation rentals near top attractions in Friendship, or you can go with a more secluded option if you'd like a relaxing place to stay.

What's the top vacation rental that Friendship has to offer?

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore: You might want to consider this vacation home rental near Friendship, which is located in the city center and offers a balcony, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Friendship?

Explore the area and family-friendly sights such as Chesapeake Beach Water Park, or get out into nature at a spot like Upper Yough River. Bayside History Museum and Rod n Reel Charter Fishing are a couple of places you'll find in the larger area.

What’s a vacation rental in Friendship like?

Vacation rentals are privately owned properties where you can stay for several days or longer in Friendship. Vacation rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a small group gathering.