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Friendship Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

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, (46 reviews)
"The place was perfect, exactly as depicted, in a lovely home in a quiet area a block from bay. It was convenient to most of Kent. The rooms are lovely and cozy with additional pullout on lower floors. I have teens so the added space was a blessing. The host was very kind and attentive checking in and offering any information to make our stay more pleasant. Checking in and out was simple and care free. I would certainly recommend it and intend to stay there again."
United States
Brian
The price is HK$726
HK$2,144 total
includes taxes & fees
28 Jun - 29 Jun
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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
9.2 out of 10, Wonderful, (9 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$1,333
HK$2,251 total
includes taxes & fees
1 Jul - 2 Jul
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
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, (22 reviews)
"Everything was exceptional! We will be back. "
United States
Kimberly F.
The price is HK$1,231
HK$3,272 total
includes taxes & fees
14 Jul - 15 Jul
Walk to Beach! King Bed & Free Beach Passes
Smart TV

3-bedroom house in Deale located on Bay many amenities and great views

3-bedroom house in Deale located on Bay many amenities and great views
Deale
3-bedroom house in Deale located on Bay many amenities and great views
Exterior detail

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is HK$882
HK$2,400 total
includes taxes & fees
29 Jun - 30 Jun
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Sun-loungers

Cottage Located on the Patuxent River!

Cottage Located on the Patuxent River!
Prince Frederick
10.0 out of 10, Exceptional, (43 reviews)
"Second time here and we love the convenience to Prince Frederick and the comfort offered by the hosts. "
United States
RACHEL S.
The price is HK$2,364
HK$2,855 total
includes taxes & fees
27 Jun - 28 Jun
Cottage Located on the Patuxent River!
Marina

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,688
HK$2,148 total
includes taxes & fees
27 Jun - 28 Jun
Sailboat Experience in Annapolis
Property grounds

Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.6 out of 10, Exceptional, (20 reviews)
"Sophia was an amazing host and the place was exactly as advertised. I couldn't recommend the place enough!"
United States
William N.
The price is HK$1,803
HK$3,000 total
includes taxes & fees
29 Jun - 30 Jun
Bright and airy waterfront getaway
Fridge, microwave, oven, stovetop

Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (8 reviews)
"Very cute house. It was exactly what I was looking for. "
United States
Collin G.
The price is HK$1,772
HK$4,728 total
includes taxes & fees
29 Jun - 30 Jun
Renovated Bungalow | Walk to Beach | Dog-Friendly
Exterior

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is HK$2,136
HK$3,606 total
includes taxes & fees
1 Jul - 2 Jul
Plum Point Cottage #17
Pool

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

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is HK$2,187
HK$4,924 total
includes taxes & fees
28 Jun - 29 Jun
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Interior

Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
10.0 out of 10, Exceptional, (5 reviews)
The price is HK$2,642
HK$4,802 total
includes taxes & fees
6 Jul - 7 Jul
Sunset Cottage - West River Access and Views!
Fridge, microwave, oven, stovetop

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (9 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is HK$1,623
HK$4,002 total
includes taxes & fees
1 Jul - 2 Jul
Cute bungalow blocks to Stadium
Interior

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is HK$2,117
HK$5,211 total
includes taxes & fees
20 Jul - 21 Jul
Annapolis Retreat - 7 mins from downtown Annapolis!
TV, offices

Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (3 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is HK$2,070
HK$5,657 total
includes taxes & fees
26 Jun - 27 Jun
Family Home on Mayo Peninsula | Deck | Sleeps 10
Dining

Franklin At The Bay

Franklin At The Bay
Deale
10.0 out of 10, Exceptional, (1 review)
"This place is beautiful, and big. The back yard is nice. We played games out back and had a cookout. Walking distance to the pier and a playground. The"
United States
Jamie C.
The price is HK$2,744
HK$5,104 total
includes taxes & fees
7 Jul - 8 Jul
Franklin At The Bay
Fridge, microwave, oven, stovetop

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is HK$2,529
HK$3,259 total
includes taxes & fees
15 Jul - 16 Jul
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
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
9.6 out of 10, Exceptional, (15 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$3,019
HK$5,721 total
includes taxes & fees
14 Jul - 15 Jul
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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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Top Friendship Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great location. Walking distance to restaurants and museums."
Lolly 3-night trip
Posted 7 hours ago
Graduate by Hilton 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:

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

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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This holiday home rental outside of Friendship is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease 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. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.