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Check prices for these dates

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29 Aug - 31 Aug
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5 Sep - 7 Sep
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19 Sep - 21 Sep
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17 Oct - 19 Oct

Cottages in Tilghman

Our top choices for Tilghman cottages

Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (255)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
Family and Pet-Friendly, Waterfront with Pier
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

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
Outdoor dining

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
Property grounds

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
Marina

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
Exterior

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
Property grounds

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!
Property grounds

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

9.6 out of 10, Exceptional, (118)
"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Waterfront property with private boat ramp and new dock!
Outdoor dining

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Marina

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

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

10.0 out of 10, Exceptional, (51)
"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
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Exterior detail

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (9)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Exterior

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
The Middle Point Cabin in Saint Michaels
Fridge, microwave, oven, stovetop

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

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

9.2 out of 10, Wonderful, (27)
"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!
Terrace/patio

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

10.0 out of 10, Exceptional, (2)
"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!
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Pool

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
On the beach, sun loungers, beach towels

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
Interior

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
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Fridge, microwave, dishwasher, coffee/tea maker

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

10.0 out of 10, Exceptional, (88)
"Beautiful property in a great location!"
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
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 Tilghman Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"This may sound like a backhanded compliment, but there was nothing spectacular about this hotel. However, everything about it was very very, very good! And sometimes, that's perfect! The hospitality was exceptional, complementary breakfast was outstanding, and the pool is in better condition than most big brand hotels out there. Room had two queen beds, and while you can tell that the hotel has been there for a while, everything was in really good condition. Conveniently located, exceptionally priced, it was exactly what we needed for a short weekend getaway. Would absolutely stay there again and certainly plan to! "
Robert 2-night trip
Posted 3 days ago
St Michaels Inn

Frequently asked questions

How much do cottages in Tilghman cost?
Cottages in Tilghman range between and per night. These properties offer a chance to get in tune with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Tilghman?
Reconnect with nature in one of the 82 cottages available in Tilghman. To help you choose a property that's right for you, use our handy filters to search for must-have amenities.
Why book your cottage in Tilghman with Expedia?
Reserving a cottage in Tilghman is as easy as deciding on your travel dates and picking your ideal place for a getaway in the outdoors. From luxurious retreats to inexpensive properties and cottages that offer perks like a hot tub, Expedia has something for all styles. As for the best deals around? We have them too!