Friendship Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Friendship vacation rentals

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
Stevensville
6.4 out of 10, (7)
"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
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.

Stevensville
10.0 out of 10, Exceptional, (15)
"The property is excellent for entertaining and family gatherings. Everything was clean and tastefully appointed."
United States
Kerrith D.
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Fridge, microwave, oven, stovetop
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic District
9.4 out of 10, Exceptional, (19)
"Great place, excellent location!"
United States
Joseph C.
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Fridge, microwave, oven, stovetop
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Historic District
10.0 out of 10, Exceptional, (33)
"Beautiful home in a great central location for walking to most downtown and USNA destinations. "
United States
Hunter S.
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Exterior
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Charming garden row home, easy 4 block walk to the heart of Annapolis.

Historic District
10.0 out of 10, Exceptional, (125)
"Great location, very clean house, wonderful stay"
United States
Kathryn O.
Charming garden row home, easy 4 block walk to the heart of Annapolis.
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

Port Republic
10.0 out of 10, Exceptional, (181)
"We thoroughly enjoyed our stay in this kitschy, cool, rustic cabin with a million-dollar view. Communing with the ospreys, hummingbirds and the bald eagle who perched numerous times on a nearby tree was an added bonus. And, the owner may be the most friendly/helpful we’ve ever rented from. We hope to be back some day. Thanks!"
United States
Brennan H.
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Outdoor pool
Beautiful Condo - Water View Near City Dock

Beautiful Condo - Water View Near City Dock

Eastport
9.6 out of 10, Exceptional, (154)
"Good location. 10 minute walk to city dock. Apartment was fine with no major issues. No problem finding parking within the parking area."
United States
Robert D.
Beautiful Condo - Water View Near City Dock
Outdoor dining
Waterfront Getaway, Dock Your Boat & Play!

Waterfront Getaway, Dock Your Boat & Play!

Edgewater
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.
Waterfront Getaway, Dock Your Boat & Play!
Exterior
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
Murray Hill
10.0 out of 10, Exceptional, (34)
"Absolutely perfect! Will stay again!!"
United States
Brian
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Fridge, microwave, oven, stovetop
Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater/Mayo Gateaway w/ Hot Tub

Edgewater
9.8 out of 10, Exceptional, (25)
"Very clean, had everything we needed for our stay!"
United States
Jackie R.
$603 nightly
The price is $650
Jan 5 - Jan 6, 2026
Total with taxes and fees
Edgewater/Mayo Gateaway w/ Hot Tub
Dining
Million Dollar View of the Chesapeake Bay

Million Dollar View of the Chesapeake Bay

Deale
9.8 out of 10, Exceptional, (130)
"Absolutely beautiful and peaceful location. Everything was appreciated- the games for lazy evenings, the crab pots, the comfortable beds and living spaces. Stunning view!"
United States
Michelle D.
Million Dollar View of the Chesapeake Bay
Interior
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville
10.0 out of 10, Exceptional, (57)
"It’s a fantastic property!! Perfect for a getaway weekend. Everything was as described. A great place to stay home and enjoy all the amenities."
United States
Kurt H.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Smart TV, fireplace, books, offices
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Port Republic
10.0 out of 10, Exceptional, (124)
"Well, what a great time we had at this house the house is exactly as advertised, tidy, clean, comfortable, everything close. The view was beautiful, our vacation was amazing. Alicia was very responsive to any question that we had. We definitely would rent again!"
United States
Misael A A.
Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier
Dining
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Cape St. John
10.0 out of 10, Exceptional, (113)
"We had a wonderful stay. The house was beautiful, clean, fully equipped and the views out back are magnificent. We all loved the pool. The host was very helpful with any issues & requests. All in all we truly enjoyed our time there. Highly recommend."
United States
Zev K.
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
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!

Eastport
10.0 out of 10, Exceptional, (126)
"We had a great stay! The house was adorable and the pool was awesome!"
United States
Kathleen J.
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Exterior
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

Hillsmere
10.0 out of 10, Exceptional, (170)
"Love the decor, the comfort and vibe of the place. Wish I had stayed longer! "
United States
Lauren m.
The Yellow Cottage on Harness Creek
Beach nearby, sun loungers, beach towels
The Blue Crab Beach House - Free beach passes

The Blue Crab Beach House - Free beach passes

North Beach
10.0 out of 10, Exceptional, (76)
"Wonderful cottage within walking distance to fun dining experiences, the beach, and the pier as well as some cute shops. Very well appointed--comfortable and clean. We enjoyed our stay and would highly recommend this cottage!"
United States
Nancy K.
The Blue Crab Beach House - Free beach passes
Fridge, microwave, oven, stovetop
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

Historic District
9.8 out of 10, Exceptional, (30)
"Pet friendly! Super cute and easy…perfect location. "
United States
Jennifer B.
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
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)
"Great location, cozy cottage, good for dogs, lots to do in and around Annapolis. "
United States
Mike F.
$327 nightly
The price is $372
Dec 10 - Dec 11
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging
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!

Historic District
10.0 out of 10, Exceptional, (241)
"We had a wonderful time staying at this property! The location was just perfect, and the host was so responsive. We would love to stay here again!"
United States
Frances A.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great"
stephen 3-night trip
Posted 11 hours ago
DoubleTree by Hilton Hotel Annapolis

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 $372 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?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : You might want to consider this vacation home rental near Friendship, which is located on a river and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a pool table.

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. Rod n Reel Charter Fishing and Chesapeake Beach Railway Museum 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.