Friendship Holiday Rentals

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Our top choices for Friendship holiday rentals

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

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Admiral Heights
10.0 out of 10, Exceptional, (89)
"Fantastic stay the house was perfect."
United States
Eric Z.
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

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.

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

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!

Beautiful Condo - Water View Near City Dock

Beautiful Condo - Water View Near City Dock
Eastport
9.6 out of 10, Exceptional, (154)
"Exceptionally clean property in a great location, convenient to DTA and the Naval Academy. The host was responsive and helpful throughout our stay. We would definitely stay here again!"
United States
Stephanie S.
Beautiful Condo - Water View Near City Dock

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

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!

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.

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.
The price is AU$989
includes taxes & fees
5 Jan - 6 Jan 2026
Edgewater/Mayo Gateaway w/ Hot Tub

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

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

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

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

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!

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

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

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

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)
"Great host, property and location. A great time!"
United States
Claudia B.
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Tracys Landing
9.8 out of 10, Exceptional, (50)
"Our week at Jacob's property was excellent. It was the perfect location for a family getaway, and Jacob was helpful and responsive."
United States
Brett F.
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
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

Find out more about Friendship

Everything you need to know about Friendship holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Friendship holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Friendship holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Friendship holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Friendship holiday rentals we have selected for you start as low as AU$989 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Friendship rentals

At Expedia, we put the best Friendship holiday 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 holiday.

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. 

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?

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres. : This holiday home rental outside of Friendship is located on a river, and has a patio, 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 fridge, a stovetop and a microwave, 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 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 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.