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Browse Select Friendship Cottages

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (224)
"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

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (162)
"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

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

9.0 out of 10, Wonderful, (26)
"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, (1)
"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!

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

10.0 out of 10, Exceptional, (50)
"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

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

10.0 out of 10, Exceptional, (213)
"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 $681
CA $1,103 total
includes taxes & fees
Aug 11 - Aug 12
Secluded Cozy Cottage in Historic Downtown

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

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

10.0 out of 10, Exceptional, (32)
"Really like this place "
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)
"The house was beautiful with everything you could need. We were out all day so didn’t get to use the house much except for sleeping. The bed was super comfortable."
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!

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (7)
"Great weekend get away if you’re just looking for some peace and quiet with some great scenery. The kitchen was immaculate and everything was as listed."
Charming Waterfront Cottage Retreat near St. Michaels

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 $414
CA $496 total
includes taxes & fees
Aug 15 - Aug 16
Cottage Located on the Patuxent River!

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

#2 Egret Cottage Harris Cove

#2 Egret Cottage Harris Cove

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 $247
CA $414 total
includes taxes & fees
Aug 17 - Aug 18
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Updated North Beach Cottage: Pet Friendly!

9.8 out of 10, Exceptional, (17)
"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)
"Emwe enjoyed our time here, it was relaxing and close to travel around the area."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
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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