Friendship Vacation Rentals

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Vacation Rentals in Friendship

Pool and Bay Views on wrap around deck in Kent Island
Outdoor pool
Pool and Bay Views on wrap around deck in Kent Island
9.6 out of 10, Exceptional, (21)
"Everyone really loved the house and the location. The pool was great"
Pool and Bay Views on wrap around deck in Kent Island
Cozy place close to the city dock
Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (55)
"We enjoyed our 2 nights at Cozy Place Close to the docks. Easy access and personalized connection with Nathalie were appreciated! We enjoyed the French and sail boating themes in the apartment, aligned the Annapolis maritime history! The docks are a short drive and old Town Annapolis was pleasant and historical! We recommend Cozy Place to others!"
Cozy place close to the city dock
Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (183)
"We stayed at this property for a week. It was nice and clean and close to the US Naval Academy! The home had everything you could need for a stay away from home. The host provided practically everything you could need as well! The host was very communicative and responded quickly as needed. We really appreciated our stay here. Thank you so much!"
Directly Across from Gate One & Steps from the Waterfront
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, (188)
"Several family members and I went on a fishing trip out of Edgewater. We stayed in this wonderful cottage on the water. The house was immaculate and everything we needed aside from food was provided. The check in and check out were very simple and the host gave us contact information in case we needed anything. The location and overall property could not have been any better. We would definitely stay here again."
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Charming Annapolis WaterVIEW Home
Property grounds
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (43)
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
The price is $399
$766 total
includes taxes & fees
Jul 10 - Jul 11
Charming Annapolis WaterVIEW Home
Chesapeake Houseboat Getaway on Kent Island, Maryland
Property grounds
Chesapeake Houseboat Getaway on Kent Island, Maryland
10.0 out of 10, Exceptional, (8)
"My husband and I both LOVED this property!!! The houseboat was beautifully decorated, so relaxing and in a great area. We cant wait to go back!"
Chesapeake Houseboat Getaway on Kent Island, Maryland
Waterfront Cottage on the Eastern Shore
Fridge, microwave, oven, stovetop
Waterfront Cottage on the Eastern Shore
9.4 out of 10, Exceptional, (3)
"Very much as pictured in ad. Convenient to we did venue we were attending"
The price is $599
$1,134 total
includes taxes & fees
Jun 19 - Jun 20
Waterfront Cottage on the Eastern Shore
Relax on Kent Island in 3 Bedroom Home w/Waterview
Exterior
Relax on Kent Island in 3 Bedroom Home w/Waterview
9.8 out of 10, Exceptional, (20)
"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"
The price is $121
$315 total
includes taxes & fees
Jun 26 - Jun 27
Relax on Kent Island in 3 Bedroom Home w/Waterview
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Property grounds
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
10.0 out of 10, Exceptional, (25)
"I chose to stay at this property for the duration of my wedding weekend. It was really great to be able to spend that extra time with family all together! Getting ready at the house, rather than a hotel was also really nice because we had much more room to space out. The make up artist and hair stylist also complimented the ample natural light and space to work. The pool and hot tub were beautiful! The only downside was a lack of curtains in the master bedroom. The sunrise is beautiful but...
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub
Entire 3-Bedroom Retreat Free Parking & Amenities
Terrace/patio
Entire 3-Bedroom Retreat Free Parking & Amenities
Entire 3-Bedroom Retreat Free Parking & Amenities
The Blue Crab Beach House - Free beach passes
Beach nearby, sun loungers, beach towels
The Blue Crab Beach House - Free beach passes
10.0 out of 10, Exceptional, (40)
"Property and home were in excellent condition. Home made us feel welcome and secure. Host provides extras that make your stay convenient. Close to the restaurants and ice cream shop that serves Hershey ice cream. Love the people and neighborhood."
The Blue Crab Beach House - Free beach passes
Indulge or be still near Naval Academy/ Annapolis
Beach
Indulge or be still near Naval Academy/ Annapolis
9.2 out of 10, Wonderful, (9)
"Great place, super neighborhood!"
Indulge or be still near Naval Academy/ Annapolis
Amazing views, short walks to great dining!
Smart TV, Netflix, DVD player, streaming services
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (66)
"Jim was amazing and answered our questions, etc. almost immediately. He was wonderful and very accommodating. Cozy cottage, loved it."
Amazing views, short walks to great dining!
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
Property grounds
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
10.0 out of 10, Exceptional, (6)
"This location was extremely clean and perfect for a weekend get away. It’s located not even 2 miles from downtown Annapolis. 10/10 would recommend"
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
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, (84)
"The house had everything we needed. Loved the decor. It created a cozy atmosphere. The backyard was amazing with the flowers and pool. The host is super!"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Bay View Studio Apartment
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (28)
"Chespeake Bay waterfront with beautiful views. Very close to Annapolis Sailing School, as well as Annapolis itself."
Bay View Studio Apartment
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
3 bedrooms, desk, iron/ironing board, free WiFi
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
10.0 out of 10, Exceptional, (102)
"Loved the house!"
Breathtaking Views, 450 pier, kayaks, fossils, priv beach, 45 min to D.C.
Anchor's Away in the Heart of Eastport!
Fridge, microwave, oven, stovetop
Anchor's Away in the Heart of Eastport!
9.8 out of 10, Exceptional, (31)
"Property is very convenient to the USNA and DTA. You can walk, but they're a good 25-30 minutes and parking was available even during Commissioning week and at the local restaurants. Plus, we could park about 25 feet from the door of the VRBO all the time. It is a first floor, easy to access door. There is a full kitchen and fridge, a comfy couch, and a nice bathroom. It's really like a nice hotel suite. A couple idiocycracies however. The bed pulls down from the wall, which gives you more play...
Anchor's Away in the Heart of Eastport!
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Fridge, microwave, oven, stovetop
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
9.4 out of 10, Exceptional, (8)
"The home was lovely. We very much enjoyed our stay. The one thing that I would recommend is direction on the heat and air. We were unable to figure out what to do The downstairs was cold and when we tried to raise the temp the upstairs was unbearably hot. I also wanted to let you know there was a leak from the ceiling in the master bedroom. Lastly, My daughter lost a small hoop earring. If you find it could you please contact me to have it returned. Thank you,"
2-story, riverfront home with private dock, inviting deck & dog-friendly yard
Don't see what you're looking for?
See all available properties in Friendship
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.

Other types of properties in Friendship you may be interested in

Historic Inns of Annapolis
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1608)
"Liked the history. close to everything!"
The price is $137
$179 total
includes taxes & fees
Jul 1 - Jul 2
Historic Inns of Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Exterior
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
2.5 star property
6.6 out of 10, (1288)
"Good "
The price is $107
$122 total
includes taxes & fees
Jun 19 - Jun 20
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Graduate Annapolis
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1022)
"We had a nice time for our baby moon!"
The price is $153
$175 total
includes taxes & fees
Jul 1 - Jul 2
Graduate Annapolis
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.

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 $121 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.

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?

Pool and Bay Views on wrap around deck in Kent Island: You might want to consider this vacation home rental near Friendship, which offers an outdoor pool, a fireplace, and a barbecue grill to help you feel perfectly comfortable 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. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

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.

Recent reviews of Friendship properties
Expedia verified reviews

The Westin Annapolis

The Westin Annapolis

5/5 Excellent
"great"
A verified traveler stayed at The Westin Annapolis
Posted 1 day ago
The Westin Annapolis