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Cottages in Friendship

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

10.0 out of 10, Exceptional, (11)
"We had a wonderful stay at the Point of a View Cottage! The views are spectacular and we also enjoyed how easy it was to walk to places to eat and the local market. Recommendations for places to eat were spot on and also appreciated a message over the weekend notifying us of the local craft market held Sunday morning. Would love to come again one day! "
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

The Middle Point Cabin in Saint Michaels

9.8 out of 10, Exceptional, (50)
"We had a great stay. The cottage is just like the pictures. Nice area…lots of things to do."
The Middle Point Cabin in Saint Michaels

Beachfront Home Minutes to Downtown Annapolis Dogs OK

9.8 out of 10, Exceptional, (36)
"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. "
Beachfront Home Minutes to Downtown Annapolis Dogs OK

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

9.2 out of 10, Wonderful, (28)
"Property was cozy and clean. Owners left lights on for us knowing we had a late arrival. Would definitely stay again. "
Cozy Cottage with access to and partially obstructed views of the bay.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (233)
"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

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

10.0 out of 10, Exceptional, (218)
"We had a wonderful time. Hosts were very kind and responsive! Beautiful property "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Secluded Cozy Cottage in Historic Downtown

9.6 out of 10, Exceptional, (14)
"We had a very lovely stay . This is an excellent location . "
The price is SAR 1,838
SAR 3,006 total
includes taxes & fees
13 Oct - 14 Oct
Secluded Cozy Cottage in Historic Downtown

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

10.0 out of 10, Exceptional, (9)
"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, (167)
"A lovely property in the perfect location! We will definitely rent again!"
The Yellow Cottage on Harness Creek

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property
10.0 out of 10, Exceptional, (6)
"Beautiful home. Very nice and quiet neighborhood on the water. "
The price is SAR 1,684
SAR 3,556 total
includes taxes & fees
26 Sep - 27 Sep
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

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

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

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

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

10.0 out of 10, Exceptional, (53)
"My wife and I have stayed at many different places over the years but this may be one of the most well maintained properties I've ever seen. It was a great place for us to unwind with our dog and we would certainly recommend this location for anyone looking to stay in the area"
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, (5)
"The owner was very nice "
The price is SAR 675
SAR 1,122 total
includes taxes & fees
24 Sep - 25 Sep
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

North Beach Cottage - Walk to Chesapeake Bay

3.0 star property
10.0 out of 10, Exceptional, (1)
"The house condition was very cleran,beautiful. we appreciate the house owner's guidance&help. we made very good memories!"
North Beach Cottage - Walk to Chesapeake Bay

Waterfront North Beach Home ~ 2 Mi to Beach!

3.0 star property
Waterfront North Beach Home ~ 2 Mi to Beach!

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

9.8 out of 10, Exceptional, (40)
"The house was very clean with all needed amentities plus. Mary was very responsive to any questions, including suggestions of local beaches. The view is incredible, especially late evening. Location wise, you are within 1-2 hours of several major cities. Will definitely plan to stay here for any future trips!"
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!

Walk to Beach: Charming Maryland Home w/ Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This little gem of a house was absolutely perfect! The house was so close to the beach and to all the places we needed to go. We were visiting from Indiana to attend my son and his wife’s baby shower! The hosts had little snacks, coffee, beach towels, etc at the ready. Everything was so clean and comfortable! Definitely give this place a 10/10! "
Walk to Beach: Charming Maryland Home w/ Yard!

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.
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Top Friendship Hotel Reviews

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