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Friendship Vacation Rentals

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Our top choices for Friendship vacation rentals

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 AED 356
AED 1,057 total
includes taxes & fees
29 Jun - 30 Jun
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

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 AED 624
AED 1,023 total
includes taxes & fees
27 Jul - 28 Jul
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

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 AED 577
AED 1,533 total
includes taxes & fees
14 Jul - 15 Jul
Walk to Beach! King Bed & Free Beach Passes

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

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 AED 433
AED 1,147 total
includes taxes & fees
30 Jun - 1 Jul
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

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 AED 1,107
AED 1,326 total
includes taxes & fees
4 Jul - 5 Jul
Cottage Located on the Patuxent River!

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
The price is AED 791
AED 1,006 total
includes taxes & fees
27 Jun - 28 Jun
Sailboat Experience in Annapolis

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 AED 845
AED 1,406 total
includes taxes & fees
29 Jun - 30 Jun
Bright and airy waterfront getaway

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 AED 871
AED 2,265 total
includes taxes & fees
29 Jun - 30 Jun
Renovated Bungalow | Walk to Beach | Dog-Friendly

Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AED 1,001
AED 1,689 total
includes taxes & fees
9 Jul - 10 Jul
Plum Point Cottage #17

Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
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 AED 1,025
AED 2,307 total
includes taxes & fees
28 Jun - 29 Jun
Family Beach House: Spacious Deck, Grill & Views

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 AED 1,216
AED 2,224 total
includes taxes & fees
7 Jul - 8 Jul
Sunset Cottage - West River Access and Views!

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 AED 760
AED 1,875 total
includes taxes & fees
1 Jul - 2 Jul
Cute bungalow blocks to Stadium

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 AED 918
AED 2,316 total
includes taxes & fees
20 Jul - 21 Jul
Annapolis Retreat - 7 mins from downtown Annapolis!

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 AED 970
AED 2,651 total
includes taxes & fees
27 Jun - 28 Jun
Family Home on Mayo Peninsula | Deck | Sleeps 10

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 AED 1,286
AED 2,391 total
includes taxes & fees
7 Jul - 8 Jul
Franklin At The Bay

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

Rose Haven Peaceful, Spacious, 3 Bedroom Retreat
Rose Haven
The price is AED 1,177
AED 1,518 total
includes taxes & fees
15 Jul - 16 Jul
Rose Haven Peaceful, Spacious, 3 Bedroom Retreat

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 AED 1,414
AED 2,680 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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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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : You might want to consider this vacation home rental near Friendship, which is located in the city center and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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.