Friendship Holiday 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
21 Apr - 22 Apr
Tomorrow
22 Apr - 23 Apr
This weekend
25 Apr - 27 Apr
Next weekend
2 May - 4 May

Holiday Rentals in Friendship

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, (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!
Chesapeake Houseboat Getaway on Kent Island, Maryland
Marina

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
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

9.8 out of 10, Exceptional, (76)
"Nothing like home away from home!! Very comfortable home. Thank you. "
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
The Blue Crab Beach House - Free beach passes
Miscellaneous

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

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 HK$5,572
HK$9,157 total
includes taxes & fees
23 Apr - 24 Apr
Grand, historic, fun, fabulous home - downtown Annapolis at Main St. & City Dock
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
View from property

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

10.0 out of 10, Exceptional, (40)
"We loved our stay. The house was spotless; Mark and Karen have provided everything one could possibly need, and they were super responsive. We enjoyed the porch, sauna, and fire pit; and our dog enjoyed the fully fenced backyard, nearby hikes, and dog-friendly local restaurants. Highly recommend!"
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
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, (34)
"Clean, Spacious, and exactly as advertised! "
The price is HK$629
HK$1,999 total
includes taxes & fees
23 Apr - 24 Apr
Relax on Kent Island in 3 Bedroom Home w/Waterview
The Cottage
Exterior

The Cottage

10.0 out of 10, Exceptional, (4)
"Beautiful, beautiful, beautiful! Haley was a wonderful host! "
The price is HK$1,513
HK$2,955 total
includes taxes & fees
27 Apr - 28 Apr
The Cottage
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
View from property

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
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
The Lazy Crab Beach House - Free beach passes
Property grounds

The Lazy Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (47)
"Enjoyed all 6 nights in this property. Manager was very responsive to all questions about the neighborhood and property. Kitchen was well stocked with pots and pans in the yard was nice to let the dog run around. "
The Lazy Crab Beach House - Free beach passes
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 HK$1,242
HK$2,402 total
includes taxes & fees
22 Apr - 23 Apr
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
On the beach

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

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
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!
Floating 2 bed 2 bath condo stunning views of the bay
Marina

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
7.4 out of 10, Good, (3)
"Next time we will wait until its a little warmer! Safe and clean marina. Great views! Peaceful and quiet. "
Floating 2 bed 2 bath condo stunning views of the bay
Cozy Cottage with access to and partially obstructed views of the bay.
Miscellaneous

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

9.2 out of 10, Wonderful, (19)
"We were traveling for a wedding at a near by venue. Plenty of room for our needs. We enjoyed visiting the small beach across the stress for coffee in the mornings! "
Cozy Cottage with access to and partially obstructed views of the bay.
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Interior

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

10.0 out of 10, Exceptional, (14)
"Was as Good as it gets. Loved the place. As close to perfect as it can get!!"
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Fridge, microwave, oven, stovetop

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
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, (1742)
"Great location!"
The price is HK$1,121
HK$1,542 total
includes taxes & fees
4 May - 5 May
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, (1575)
"Room spacious...great..."
The price is HK$679
HK$776 total
includes taxes & fees
27 Apr - 28 Apr
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Country Inn & Suites by Radisson, Annapolis, MD
Hypo-allergenic bedding, desk, blackout curtains, iron/ironing board

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1009)
"amazing stay. very relaxing. was quiet despite they were booked full. only issue i had was half my room was got and half was cold. "
The price is HK$751
HK$856 total
includes taxes & fees
28 Apr - 29 Apr
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 holiday rentals in Friendship?

Yes, there are holiday rentals close to the most popular sights in Friendship, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Friendship has to offer?

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore: This holiday home rental outside of Friendship is located in the city centre, 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 that 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 wider area.

What’s a holiday rental in Friendship like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Friendship. Holiday rentals offer amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of security away from public hotel lifts and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.