Friendship Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Holiday Rentals in Friendship

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Marina

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (234)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Fridge, microwave, oven, stovetop

Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.

10.0 out of 10, Exceptional, (13)
"The host was amazing. The property was as described and was perfect for our group. "
Woodland Retreat on Kent Island: 5 beds, 5 miles from Bay Bridge, on 5 acres.
Floating 2 bed 2 bath condo stunning views of the bay
Marina

Floating 2 bed 2 bath condo stunning views of the bay

2.0 star property
6.8 out of 10, (5)
"Beautiful view! Could hear the tiki bar music from the top. Easy to get to woth lots of things to do nearby. "
Floating 2 bed 2 bath condo stunning views of the bay
Waterfront Getaway, Dock Your Boat & Play!
Outdoor dining

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is NZ$559
includes taxes & fees
21 Oct - 22 Oct
Waterfront Getaway, Dock Your Boat & Play!
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Outdoor dining

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

9.8 out of 10, Exceptional, (47)
"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!"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Fridge, microwave, oven, stovetop

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (16)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
The price is NZ$2,127
includes taxes & fees
3 Nov - 4 Nov
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Charming townhome with AC and WiFi in delightful Annapolis
Interior

Charming townhome with AC and WiFi in delightful Annapolis

4.0 out of 10, (1)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
The price is NZ$176
includes taxes & fees
4 Nov - 5 Nov
Charming townhome with AC and WiFi in delightful Annapolis
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Dining

Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay

10.0 out of 10, Exceptional, (179)
"Cottage was just as pictured. Lots of character and charm. Host, Brett was easy to work with and very helpful!"
Stunning Views from Waterfront Log Cabin With Fireplace On The Chesapeake Bay
Walk to Everything House
Fridge, microwave, oven, stovetop

Walk to Everything House

10.0 out of 10, Exceptional, (83)
"Clean and nice place to stay"
Walk to Everything House
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (218)
"We had a wonderful time. Hosts were very kind and responsive! Beautiful property "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Riverfront Retreat 7mil from MD Renaissance Fest!
Exterior

Riverfront Retreat 7mil from MD Renaissance Fest!

9.2 out of 10, Wonderful, (17)
"It was a beautiful and private setting for a family reunion."
Riverfront Retreat 7mil from MD Renaissance Fest!
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Exterior

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

2.5 star property
10.0 out of 10, Exceptional, (28)
"Absolutely the best Vrbo we have ever encountered! Beautiful, charming, accommodating, family friendly and in an excellent location. Our stay was exceptional. "
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
18th Cent. Charm in Historic Downtown Annapolis
Fridge, microwave, oven, stovetop

18th Cent. Charm in Historic Downtown Annapolis

9.0 out of 10, Wonderful, (12)
"Property description is accurate, host is quickly responsive."
The price is NZ$590
includes taxes & fees
5 Oct - 6 Oct
18th Cent. Charm in Historic Downtown Annapolis
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (122)
"My family had a great time staying here during a lacrosse tournament. Host was the best and the house was great. My boys loved the pool and adults loved the proximity to the restaurants and bars. Will stay here again in future. "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Private beach

6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access

10.0 out of 10, Exceptional, (16)
"Gorgeous views and location. "
6BR Waterfront Estate | Private Dock, Firepit, Screened Porch & Beach Access
Cozy Cottage with access to and partially obstructed views of the bay.
Fridge, microwave, oven, stovetop

Cozy Cottage with access to and partially obstructed views of the bay.

9.0 out of 10, Wonderful, (29)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.
Million Dollar View of the Chesapeake Bay
Dining

Million Dollar View of the Chesapeake Bay

9.8 out of 10, Exceptional, (126)
"We really enjoyed the beautiful house and wonderful bay views from the windows. Our host was very helpful and communicative too. Wish we could have stayed longer!"
Million Dollar View of the Chesapeake Bay
Relax on Kent Island in 3 Bedroom Home w/Waterview
Marina

Relax on Kent Island in 3 Bedroom Home w/Waterview

9.8 out of 10, Exceptional, (40)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
The price is NZ$427
includes taxes & fees
6 Oct - 7 Oct
Relax on Kent Island in 3 Bedroom Home w/Waterview
One-level waterfront home with beach and stunning views all the way to the Bay Bridge
Smart TV

One-level waterfront home with beach and stunning views all the way to the Bay Bridge

2.0 star property
9.8 out of 10, Exceptional, (13)
"We had a great time. The home was clean with beautiful views. Highly recommend."
One-level waterfront home with beach and stunning views all the way to the Bay Bridge
The Yellow Cottage on Harness Creek
Exterior

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (168)
"A lovely property in the perfect location! We will definitely rent again!"
The Yellow Cottage on Harness Creek
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

Hilton Garden Inn Annapolis Downtown

Hilton Garden Inn Annapolis Downtown

10/10 Excellent
"Great"
BRIAN 2-night trip
Posted 4 days ago
Hilton Garden Inn Annapolis Downtown

Find out more about Friendship

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 favorite 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 depends 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 NZ$176 per night. Entering your travel dates in the search wizard you might find 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. 

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.