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Browse Select Shady Side 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

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (184)
"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (122)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (142)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (119)
"We once again enjoyed our stay here. Perfect location to every where you’d want to go in St. Michael’s! Loved sitting out front looking at the water and park and enjoying music from our front yard. Highly recommend this cottage."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

"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

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

10.0 out of 10, Exceptional, (51)
"This exceptional property was our best homestay experience yet across several states and countries. The unit has so many customized features that make it stand out, from the fire pit (fire already built) and sauna (water bucket already filled) to the kitchen and bedrooms, where no detail has been missed. The owners were extremely proactive and responsive throughout our stay, and we look forward to booking again soon. "
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, (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 £606
includes taxes & fees
27 Aug - 28 Aug
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

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

10.0 out of 10, Exceptional, (3)
"The house was in a perfect location. Close to the beach and restaurants. The home was very comfortable, cozy and thoughtfully decorated. We will definitely be back!"
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

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.
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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Shady Side Cottages information

Number of reviews
1,338
Accommodation
73 Cottages
Lowest Price
£606
Highest Price
£606