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Compare Cottages in Friendship with updated reviews, rates, and availability.

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

9.6 out of 10, Exceptional, (17)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.

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

10.0 out of 10, Exceptional, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (220)
"This was a winter getaway to a very comfortable house with all the amenities on a quiet tributary of the Chesapeake. A rare vacation for and just what we wanted. Conveniently located near St Michael’s and Easton. Communication was excellent and everything was just as described. Would go back if we get the opportunity. "
Relaxing Waterfront Cottage Near St Michaels, Maryland

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

10.0 out of 10, Exceptional, (207)
"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

Enchanting West River Retreat

10.0 out of 10, Exceptional, (8)
"Trip from Denver to see our son at the academy. Place was all that was advertised - clean, well appointed, comfortable, nice neighborhood. Its not far from the academy in terms of miles but you have to travel a lot of backroads to get there. We enjoyed our stay and would stay here again. "
Enchanting West River Retreat

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)
"Great location for a wedding stay. Beautiful home, professionally managed!"
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

Pet-friendly Annapolis Home: Walk to Beach!

3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (77)
"Very well-maintained property in a quiet neighborhood. Although we didn't need anything, host was always available."
Amazing views, short walks to great dining!

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (7)
"Such a wonderful experience staying in this poperty for a couple of days. Walking distance to everything. Jennifer was a pleasure and very responsive. May make this an annual visit! Loved Annapolis!"
The price is SAR 1,500
SAR 2,540 total
includes taxes & fees
10 Feb - 11 Feb
Secluded Cozy Cottage in Historic Downtown

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels

Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

10.0 out of 10, Exceptional, (26)
"Amazing house! perfect for my family and our stay in Annapolis. Perfect location to everything. We had all of the amenities we needed and everything was easy to use. If I had one thing negative to say, I wish I could have had my dogs with us, I would have gladly paid a cleaning fee to have them there. Luckily I was able to make other arrangements. Thank you for sharing your house with my family!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"Beautiful, tranquil setting. Hostess was very accommodating. Access to all of the right elements: kayaks, fire pitfire, plenty of outdoor seating, tiki torches, gas grill and more. "
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (41)
"Nice place to stay for work trip. "
The price is SAR 600
SAR 1,161 total
includes taxes & fees
21 Feb - 22 Feb
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

9.8 out of 10, Exceptional, (29)
"My stay was wonderful, listing just as described. Beautiful water views and enjoyed the local area. Highly recommend and plan to return. Thank you so much for a lovely stay!"
Waterfront dog-friendly home with beach just mins to Downtown Annapolis

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

9.8 out of 10, Exceptional, (22)
"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

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

9.0 out of 10, Wonderful, (2)
"The owner was very nice "
The price is SAR 750
SAR 1,210 total
includes taxes & fees
21 Feb - 22 Feb
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

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

9.8 out of 10, Exceptional, (34)
"A beautiful stay on the Chesapeake."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Updated North Beach Cottage: Pet Friendly!

10.0 out of 10, Exceptional, (13)
"Adorable cottage with updated amenities. A great retreat for friends or a family!! "
Updated North Beach Cottage: Pet Friendly!

The Middle Point Cabin in Saint Michaels

9.8 out of 10, Exceptional, (48)
"nice property. secluded. clean and comfortable. owners very very responsive. "
The Middle Point Cabin in Saint Michaels
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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Other property types in Friendship

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

9.8 out of 10, Exceptional, (38)
"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

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

10.0 out of 10, Exceptional, (206)
"Great property and location to everything is ideal. Would definitely book this place again. "
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore

9.8 out of 10, Exceptional, (66)
"The place was clean, well-maintained, and exactly as described. The host was incredibly responsive and helpful"
Beautiful family sized townhouse with deck. Close to Washington DC and Baltimore
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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