Friendship Vacation Rentals

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Oct 23 - Oct 24
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Oct 31 - Nov 2

Vacation Rentals in Friendship

Fridge, microwave, oven, stovetop
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
10.0 out of 10, Exceptional, (14)
"Everything was exactly as described on the listing. It’s the perfect spot for a peaceful and relaxing getaway, all while being close to a charming town. The hosts were very pleasant and easy to communicate with. I highly recommend this place! "
United States
Michael T.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Outdoor dining
The Cozy Crab- Your Charming Haven in Lovely North Beach!
The Cozy Crab- Your Charming Haven in Lovely North Beach!
9.8 out of 10, Exceptional, (12)
"Great place. Just a short drive to town with shops, restaurants, and boardwalk."
United States
scott
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Outdoor dining
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
9.8 out of 10, Exceptional, (50)
"Our large family of adults and two one-year-olds and a dog had a perfect week. The hosts were kind and responsive, and the home was spacious with lots of room for privacy and being all together. Looking forward to going again!"
United States
Lynne J.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Marina
Floating 2 bed 2 bath condo stunning views of the bay
Floating 2 bed 2 bath condo stunning views of the bay
2.0 star property
7.0 out of 10, Good, (6)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
United States
Natalia F.
Floating 2 bed 2 bath condo stunning views of the bay
Dining
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
10.0 out of 10, Exceptional, (180)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
United States
Michelle R.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!
Waterfront Getaway, Dock Your Boat & Play!
10.0 out of 10, Exceptional, (3)
"Great place to stay. It is clean, comfortable, and not lacking convenience.Quick communication with the host. We would definitely recommend!"
United States
Daniel K.
$289 nightly
The price is $308
Oct 27 - Oct 28
Total with taxes and fees
Waterfront Getaway, Dock Your Boat & Play!
Dining
Million Dollar View of the Chesapeake Bay
Million Dollar View of the Chesapeake Bay
9.8 out of 10, Exceptional, (129)
"We just enjoyed our fourth year at Million Dollar View of the Chesapeake Bay and already look forward to our next vacation at this wonderful home!"
United States
Melissa G.
Million Dollar View of the Chesapeake Bay
Dining
Waterfront- 5-bedroom house with dock in charming North Beach
Waterfront- 5-bedroom house with dock in charming North Beach
2.0 star property
10.0 out of 10, Exceptional, (2)
"Lovely home with beautiful views of the Bay. Very spacious and well appointed. The hosts were very responsive to our questions. Great place to celebrate our birthdays with all the family including grandkids. Very convenient to North Beach. "
United States
ellen p.
Waterfront- 5-bedroom house with dock in charming North Beach
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (123)
"We really enjoyed our stay at this cozy cottage with an amazing backyard retreat. We had the pleasure of meeting our host Liz and she is super nice and extremely responsive. We are so happy we found this cottage and hope to have future visits. "
United States
Petra L.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Marina
Relax on Kent Island in 3 Bedroom Home w/Waterview
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (41)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
$296 nightly
The price is $314
Nov 16 - Nov 17
Total with taxes and fees
Relax on Kent Island in 3 Bedroom Home w/Waterview
Fridge, microwave, oven, stovetop
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
10.0 out of 10, Exceptional, (30)
"Great location for our team to stay during Annapolis sail show. "
United States
Anonymous traveler
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Exterior
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (220)
"Very nice place, we will be visiting again!"
United States
Karen B.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Private beach
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
10.0 out of 10, Exceptional, (18)
"House was great and the golf cart excellent"
United States
Bradley E.
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Marina
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (237)
"This was a wonderful historic home to vacation in"
United States
Amy N.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub
Edgewater/Mayo Gateaway w/ Hot Tub
9.8 out of 10, Exceptional, (23)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
$545 nightly
The price is $584
Oct 30 - Oct 31
Total with taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub
On the beach
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.
9.6 out of 10, Exceptional, (5)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
United States
Berenice N.
$271 nightly
The price is $299
Oct 24 - Oct 25
Total with taxes and fees
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Fridge, microwave, oven, stovetop
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
9.8 out of 10, Exceptional, (43)
"House was beautiful! Right on the bay and easily accommodated our group. "
United States
James T.
Waterfront Home on the Chesapeake Bay with Pier only 30 min from naval academy
Fridge, microwave, oven, stovetop
18th Cent. Charm in Historic Downtown Annapolis
18th Cent. Charm in Historic Downtown Annapolis
9.0 out of 10, Wonderful, (12)
"Property description is accurate, host is quickly responsive."
United States
Bradford R.
$325 nightly
The price is $371
Oct 27 - Oct 28
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop
Walk to Everything House
Walk to Everything House
10.0 out of 10, Exceptional, (83)
"Great location to all shopping and restaurants! Walk to Blue Crab coffee behind back yard! "
United States
Kim D.
Walk to Everything House
Fridge, microwave, oven, stovetop
Sweet Bamboo Beach Cottage
Sweet Bamboo Beach Cottage
9.8 out of 10, Exceptional, (80)
"Cute and clean house..close to beach and restaurants!! We will visit again !"
United States
Deborah O.
Sweet Bamboo Beach Cottage
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

Holiday Inn Express Washington DC East - Andrews AFB by IHG

Holiday Inn Express Washington DC East - Andrews AFB by IHG

10/10 Excellent
"Cool stay"
Cedrick 2-night trip
Posted 20 hours ago
Holiday Inn Express Washington DC East - Andrews AFB by IHG

Find out more about Friendship

Everything you need to know about Friendship vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Friendship vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Friendship vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Friendship vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Friendship. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Friendship in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $299 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Friendship rentals

At Expedia, we put the best Friendship vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Friendship rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Friendship vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Friendship. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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! : Visitors like this Friendship vacation home rental. It 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.