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Compare 59 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, (14)
"Enjoy our time there"
Cozy Cottage with access to and partially obstructed views of the bay.

Amazing views, short walks to great dining!

10.0 out of 10, Exceptional, (76)
"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!

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland

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

9.8 out of 10, Exceptional, (33)
"A beautiful stay on the Chesapeake."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

"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

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

10.0 out of 10, Exceptional, (204)
"Very cozy and clean. Beautiful surroundings with direct view of the water. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

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

Secluded Cozy Cottage in Historic Downtown

10.0 out of 10, Exceptional, (6)
"This little cottage was in an extremely convenient location. All needs within walking distance. Parking wasn’t bad - quick walk from garage. Overall would consider again!! "
The price is SAR 1,409
SAR 2,424 total
includes taxes & fees
7 Jan - 8 January 2025
Secluded Cozy Cottage in Historic Downtown

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

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

Pet-friendly Annapolis Home: Walk to Beach!

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

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

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (156)
"This was a great place to relax, have time to disconnect, and time to enjoy the company of my good friend. Loved the location and walked to the winery for a fabulous afternoon picnic. "
The Yellow Cottage on Harness Creek

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

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

10.0 out of 10, Exceptional, (40)
"Nice place to stay for work trip. "
The price is SAR 421
SAR 952 total
includes taxes & fees
5 Jan - 6 January 2025
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

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

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

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

10.0 out of 10, Exceptional, (25)
"Property as described. Very clean. Appreciated having shampoo/linens. Check out easy as well. Would recommend!"
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (28)
"This little farmhouse is great. Updated and very clean with an unbelievable location just a short walk to the beach. "
North Beach Cottage - Walk to Chesapeake Bay

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (38)
"The property and the cottage are just beautiful [very quiet] and incredibly well appointed. The bed is super cozy. There is no kitchen but the coffee station was great to have. Note that the cottage shares the property with the main house. My husband and I enjoyed sitting by the river multiple times during our stay and we really appreciated our hosts’ hospitality and communication. Thank you for the beautiful respite!"
The price is SAR 1,108
SAR 1,338 total
includes taxes & fees
1 Jan - 2 January 2025
Cottage Located on the Patuxent River!
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

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

10.0 out of 10, Exceptional, (205)
"A great experience all around"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

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

9.8 out of 10, Exceptional, (37)
"This home was perfect for our 12-person family. There was plenty of room to spread out, and the house was well stocked with everything we needed. It would be a great place to vacation in the summer as well. The owner was helpful, communicated well, and accommodating. We hope we can return sometime in the future."
Spacious 5-Bedroom Waterfront Oasis with Private Dock, Pool and Hot Tub

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (217)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
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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