Default HTG hotel image

Friendship Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Friendship holiday rentals

A modern kitchen with a central island, stainless steel appliances, and a window with butterfly decals.

1. The Cozy Crab- Your Charming Haven in Lovely North Beach!

The Cozy Crab- Your Charming Haven in Lovely North Beach!
North Beach
9.6 out of 10, Exceptional, (30 reviews)
"Wonderful place to visit "
United States
James L.
The price is AU$438
includes taxes & fees
2 Nov - 3 Nov
The Cozy Crab- Your Charming Haven in Lovely North Beach!
Living area

2. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (25 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is AU$407
includes taxes & fees
2 Nov - 3 Nov
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A house with a yellow door and a window with a lamp outside.

3. 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.
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
A cozy outdoor seating area with a fire pit, a wooden table, and chairs.

4. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (40 reviews)
"This property and host were excellent. Property was as advertised. Lovely, clean, quiet and comfortable. Owner was super responsive and check in and check out was easy. 100% recommend."
United States
Sarah
The price is AU$682
includes taxes & fees
16 Nov - 17 Nov
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A living room with a sofa, coffee table, fireplace, and artwork on the wall.

5. 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
10.0 out of 10, Exceptional, (1 review)
"Everything at this location was as shown on the listing and it was very clean. We were very satisfied with all elements of this stay. We were there for a weekend and did not use the place heavily, but it suited our needs. It's a quiet location. They had all the major points covered. The only negative comment I have is that the water out of the tap was smelly. I suggest bringing a couple of bottles of water and not drinking the water out of the taps. This is obviously a well maintained home...
United States
Amelia
The price is AU$613
includes taxes & fees
2 Nov - 3 Nov
3-bedroom house in Deale located on Bay many amenities and great views
A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

6. 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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is AU$508
includes taxes & fees
23 Nov - 24 Nov
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A modern kitchen with a large window, a dishwasher, and a ceiling fan.

7. Sunset Cottage - West River Access and Views!

Sunset Cottage - West River Access and Views!
Shady Side
9.8 out of 10, Exceptional, (6 reviews)
"Our family enjoyed staying at the Sunset Cottage. It was clean, had everything we needed for a great trip and the communion was amazing."
United States
Michelle H.
The price is AU$579
includes taxes & fees
4 Nov - 5 Nov
Sunset Cottage - West River Access and Views!
A deck with outdoor furniture, a red door, and a house with windows.

8. 3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access

3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
Shady Side
9.0 out of 10, Wonderful, (2 reviews)
"The location was spectacular, the host was communicative, and we had a great time! A beautiful and clean home with everything needed to make a trip a success. One small issue with some needed essentials meant a quick run to the store (TP!) but otherwise a great location, great stay, and would stay again!"
United States
David S.
The price is AU$505
includes taxes & fees
16 Nov - 17 Nov
3-bedroom house in tranquil Shady Side with RV/EV Charger and Beach Access
A kitchen with a bar area, a ceiling fan, and a sliding glass door leading to a deck.

9. Renovated Bungalow | Walk to Beach | Dog-Friendly

Renovated Bungalow | Walk to Beach | Dog-Friendly
Edgewater
9.6 out of 10, Exceptional, (14 reviews)
"This is a cute place. Well stocked nicely renovated kitchen. Having coffee and a bottle of wine was a definite plus. "
United States
Diane D.
The price is AU$755
includes taxes & fees
4 Nov - 5 Nov
Renovated Bungalow | Walk to Beach | Dog-Friendly
Downstairs living Space

10. Beach Front, Bay View, Fishing, chesapeake,Family Getaway

Beach Front, Bay View, Fishing, chesapeake,Family Getaway
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Very clean and nice property"
United States
Ben W.
The price is AU$573
includes taxes & fees
3 Nov - 4 Nov
Beach Front, Bay View, Fishing, chesapeake,Family Getaway
A spacious living room with a grey sectional sofa, a round wooden coffee table, and a patterned rug.

11. Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
Prince Frederick
9.2 out of 10, Wonderful, (12 reviews)
"A great place to crash and explore the area."
United States
Sean B.
The price is AU$418
includes taxes & fees
2 Nov - 3 Nov
Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.
A modern living room with a sofa, armchair, and coffee table. A kitchen with white cabinets and appliances is visible in the background.

12. Family Home on Mayo Peninsula | Deck | Sleeps 10

Family Home on Mayo Peninsula | Deck | Sleeps 10
Edgewater
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and comfortable. Great layout. "
United States
Kristin G.
The price is AU$962
includes taxes & fees
3 Nov - 4 Nov
Family Home on Mayo Peninsula | Deck | Sleeps 10
Fire pit (2)

13. Plum Point Cottage #17

Plum Point Cottage #17
Huntingtown
The price is AU$636
includes taxes & fees
2 Nov - 3 Nov
Plum Point Cottage #17
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

14. 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
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is AU$374
includes taxes & fees
2 Nov - 3 Nov
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Fire pit (2)

15. Plum Point Cottage #14

Plum Point Cottage #14
Huntingtown
9.8 out of 10, Exceptional, (9 reviews)
"we had a great stay at this property for an impromptu weekend getaway. "
United States
Yonnick H.
The price is AU$748
includes taxes & fees
9 Nov - 10 Nov
Plum Point Cottage #14
Fire pit (2)

16. Plum Point Cottage #15

Plum Point Cottage #15
Maryland
The price is AU$793
includes taxes & fees
2 Nov - 3 Nov
Plum Point Cottage #15
A hot tub with a white deck and railing, surrounded by trees and a house in the background.

17. 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, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is AU$640
includes taxes & fees
3 Nov - 4 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern kitchen with white cabinets, stainless steel appliances, and a central island with bar stools.

18. Londontowne Home | Beach | 3BR

Londontowne Home | Beach | 3BR
Edgewater
9.4 out of 10, Exceptional, (3 reviews)
"The property was beautiful with plenty of space to have a getaway with friends. The host was super communicative when we had issues with check in. Would highly recommend staying here!"
United States
Sam A.
The price is AU$1,012
includes taxes & fees
3 Nov - 4 Nov
Londontowne Home | Beach | 3BR
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

19. 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 AU$777
includes taxes & fees
9 Nov - 10 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
A lakeside view with chairs and a table, a rainbow, and trees.

20. Bright and airy waterfront getaway

Bright and airy waterfront getaway
Benedict
9.8 out of 10, Exceptional, (26 reviews)
"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."
United States
George
The price is AU$514
includes taxes & fees
2 Nov - 3 Nov
Bright and airy waterfront getaway
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Friendship Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"The gentleman that was allowed to smoke a joint at the entrance was not appropriate. Someone should of asked him to relocate."
Michael 1-night trip
Posted 5 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

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$374 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?

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach: This holiday home rental outside of Friendship is located near the beach, and has a fireplace, a balcony 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. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.