Friendship Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Friendship holiday rentals

Exterior

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is HK$503
HK$1,902 total
includes taxes & fees
3 Mar - 4 Mar
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby

Walk to Beach! King Bed & Free Beach Passes

Walk to Beach! King Bed & Free Beach Passes
North Beach
10.0 out of 10, Exceptional, (19 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is HK$529
HK$2,398 total
includes taxes & fees
3 Mar - 4 Mar
Walk to Beach! King Bed & Free Beach Passes
Property grounds

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Benedict
9.0 out of 10, Wonderful, (8 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is HK$1,197
HK$2,098 total
includes taxes & fees
3 Mar - 4 Mar
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Pool

Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.0 out of 10, Wonderful, (6 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$1,330
HK$3,431 total
includes taxes & fees
18 Mar - 19 Mar
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,348
HK$3,793 total
includes taxes & fees
3 Mar - 4 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Beach nearby, sun-loungers, beach towels

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is HK$1,795
HK$4,125 total
includes taxes & fees
3 Mar - 4 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
TV, offices

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

Wright's Cottage- Pet's Welcome & EV Charging
Annapolis
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is HK$1,325
HK$2,840 total
includes taxes & fees
23 Mar - 24 Mar
Wright's Cottage- Pet's Welcome & EV Charging
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (42 reviews)
"The accommodations were superb and being on the water was amazing!"
United States
Daniel P.
The price is HK$2,077
HK$2,509 total
includes taxes & fees
3 Mar - 4 Mar
Cottage Located on the Patuxent River!
Smart TV

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (14 reviews)
"Second time staying at this lovely, serene home/property. It’s the perfect getaway if you’re looking to escape into some peace! Highly recommend "
United States
Jill C.
The price is HK$2,052
HK$4,141 total
includes taxes & fees
4 Mar - 5 Mar
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Smart TV

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side

Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Shady Side
10.0 out of 10, Exceptional, (4 reviews)
"Would stay here again "
United States
Thomas D.
The price is HK$1,218
HK$3,476 total
includes taxes & fees
8 Mar - 9 Mar
Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side
Beach

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Prince Frederick
10.0 out of 10, Exceptional, (8 reviews)
"Such a cool neighborhood! Easy walk to an amazing private beach. Would love to stay again. "
United States
Olivia M.
The price is HK$1,878
HK$3,441 total
includes taxes & fees
16 Mar - 17 Mar
2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!
Smart TV, books

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.6 out of 10, Exceptional, (5 reviews)
"We had a short stay after a sporting event in DC, it was a little less than an hour away. Convenient location and a very clean house. Kitchen was well stocked. There was little communication with the owner, which was nice vs a long list of rules, but we would have liked to know any of their local specific favorite spots or more detailed check in/check out. Worked out nicely for our family. "
United States
Carrie K.
The price is HK$1,580
HK$3,027 total
includes taxes & fees
30 Mar - 31 Mar
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Oven, stovetop

40' Bristol sailboat with spectacular views

40' Bristol sailboat with spectacular views
Stevensville
The price is HK$2,347
HK$3,392 total
includes taxes & fees
3 Mar - 4 Mar
40' Bristol sailboat with spectacular views
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is HK$1,166
HK$4,096 total
includes taxes & fees
5 Mar - 6 Mar
Cute bungalow blocks to Stadium
Beach

Cozy Beach Retreat - 3 bedrooms with 3 queen size beds. Sleeps 6

Cozy Beach Retreat - 3 bedrooms with 3 queen size beds. Sleeps 6
Saint Leonard
The price is HK$1,408
HK$3,110 total
includes taxes & fees
4 Mar - 5 Mar
Cozy Beach Retreat - 3 bedrooms with 3 queen size beds. Sleeps 6
Outdoor dining

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (32 reviews)
"Perfect place to spend quality time with our three adult children and their significant others. "
United States
Malarkey F.
The price is HK$1,416
HK$3,982 total
includes taxes & fees
17 Mar - 18 Mar
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$1,244
HK$4,067 total
includes taxes & fees
3 Mar - 4 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
The price is HK$1,580
HK$3,566 total
includes taxes & fees
8 Mar - 9 Mar
Sunset Cottage - West River Access and Views!
Smart TV, fireplace, table football, ping pong

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is HK$1,854
HK$4,201 total
includes taxes & fees
3 Mar - 4 Mar
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Friendship Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Everything was perfect "
Corahnida 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis

Find out more about Friendship

Search for holiday rentals in Friendship on Expedia! You can easily find your home rentals, villas, holiday apartments in Friendship using one of the methods below:

  • View our selection of featured holiday rentals in Friendship
  • Use the map to find apartments and other holiday homes in the Friendship neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Friendship while they last

Look no further and take a look at our great range of rental properties in Friendship!

Explore a world of travel with Expedia

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?

Charming Annapolis WaterVIEW Home: This holiday home rental outside of Friendship is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

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.