Search Friendship Cottage Rentals from CA $250

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Browse Select Friendship Cottages

Our top choices for Friendship cottages

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (226)
"We had a lovely stay here.Place was VERY clean.Visited St. Michael’s and relaxed on the porch & pier.It met our expectations."
Relaxing Waterfront Cottage Near St Michaels, Maryland

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (7)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (164)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (11)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

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

10.0 out of 10, Exceptional, (51)
"Beautiful home with LOTS of attention to detail. The backyard was a beautiful oasis and we LOVED the “swing bed” on the screened-in porch. Mark and Karen add lots of fine touches to make your stay special. Plenty of room for two, cozy for four, and comfortable for four legged friends with the fenced in back yard. Quiet and private with a short 10 minute drive to town. Can’t wait to return!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is CA $250
CA $415 total
includes taxes & fees
Aug 24 - Aug 25
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

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

10.0 out of 10, Exceptional, (214)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
The price is CA $624
CA $1,030 total
includes taxes & fees
Aug 24 - Aug 25
Secluded Cozy Cottage in Historic Downtown

The Middle Point Cabin in Saint Michaels

9.8 out of 10, Exceptional, (49)
"The property was beautiful, quiet, and peaceful. It was a good refresh from daily life in the city."
The Middle Point Cabin in Saint Michaels

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

9.2 out of 10, Wonderful, (27)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.

Quick walk to the beach! Fire pit, Corn hole, Games & More!

10.0 out of 10, Exceptional, (2)
"We loved EVERYTHING about this place. Right next to the beach, great restaurants and shops. Could not have been better service. "
Quick walk to the beach! Fire pit, Corn hole, Games & More!

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

9.8 out of 10, Exceptional, (34)
"We wanted to celebrate my wife’s birthday with some friends, and a bushel of crabs…and what an incredible house to host a special occasion. The kids had the water/mini beach and plenty of yard space to play; there was a space outside to eat the crabs; and the house was incredibly clean and inviting. "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (37)
"Beautiful, charming house! The owner was wonderful! She had a lovely card waiting for us with a handwritten note. Really warm welcome! Also great location!"
North Beach Cottage - Walk to Chesapeake Bay

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

9.6 out of 10, Exceptional, (91)
"We had a great time at this place. Close enough to walk to town if necessary would definitely book again for a weekend getaway."
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (39)
"The accommodations were superb and being on the water was amazing!"
The price is CA $418
CA $501 total
includes taxes & fees
Aug 22 - Aug 23
Cottage Located on the Patuxent River!

Updated North Beach Cottage: Pet Friendly!

9.8 out of 10, Exceptional, (19)
"Awesome house a very short walk from Herrington Harbour."
Updated North Beach Cottage: Pet Friendly!

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

9.8 out of 10, Exceptional, (39)
"Great property in beautiful neighborhood with incredible views. Private pier and front porch were extras! "
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

3.0 star property
Luxe Chesapeake Bay Getaway < 20 Mi to 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Friendship Hotel Reviews