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Compare 66 Cottages in Tilghman with updated reviews, rates, and availability.

Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (211)
"As always our stay was amazing from kayaking, bird watching, sunsets. The cove is a special place."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Living room
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (38)
"My sister and I came back for the 2nd year in a row. We love your property. It’s got everything we needed. A nice pool and gazebo with a stunning view. "
The price is SAR 499
SAR 1,054 total
includes taxes & fees
24 Sep - 25 Sep
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (148)
"This was just a super place- right in the water and beautiful… and surprisingly spacious for a cottage. I loved the kitchen farm sink and the sun coming in the morning off the bay. Will definitely love to stay again. The owner was so nice and thought of all the little details!! Thank you!!"
The Yellow Cottage on Harness Creek
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Front of house from St. Michaels harbor looking across Town Park
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (107)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Eastern Shore Waterside Cottage Near St. Michaels
wrap around porch with rockers and dining area
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (18)
"We had a great stay at this house. We enjoyed using the kayak and paddleboard. (Access to the water is across this street.) We also enjoyed the pool and relaxing on the porch. It was about a 15 minute drive into St Michael’s, where we had excellent meals, went sailing, and enjoyed the cute shops and pretty houses. It was a really nice, relaxing weekend! "
Eastern Shore Waterside Cottage Near St. Michaels
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Blue heron sunset
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (5)
"Our stay was amazing! Words cannot say enough! The view is magical. We enjoyed coffee on the porch to watch the sunrise and the crab/oyster boats going in and out. Maria, is a wonderful and very thoughtful host. At her recommendation, we went to the free wine tasting at the General Store at the end of the street. We met several local residents who could not be more kind and fun to talk with. We can't wait to come back and stay again."
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Exterior
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
10.0 out of 10, Exceptional, (1)
"If you want to get away from it all, this is the place to be. My wife and I celebrated our 20th wedding Anniversary. Calm and peaceful, nestled right by the Choptank River. The cottage itself was very comfortable. The air conditioner worked great. It was a pleasure staying there and we will probably return next year."
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Cozy retreat in peaceful wooded setting. Pet friendly!
Path to cottage
Cozy retreat in peaceful wooded setting. Pet friendly!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Private country setting with a short drive to civilization. Small studio style home easy to get around with open setting. Owners are super friendly and easy to communicate with"
Cozy retreat in peaceful wooded setting. Pet friendly!
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (199)
"What a lovely hideaway!!! The owners are extremely hospitable and the area is beautiful quaint and close to everything. Thank you for having us!!!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Front of Carpenter St. Cottage
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (165)
"Great little cottage and plenty of space for our family of 3 to have an end-of-Summer getaway to one of our favorite towns. Prompt and easy communication with the owner, Tom, both before and during our stay. We loved the back porch and were blessed with some cooler temps and were able to enjoy sitting out there. FYI - Den has a door (third bedroom with pull out sofa). We have rented on Carpenter Street before, and the location cannot be beat as far as walkability to everything in town and along...
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Front and side view of Blades House from Locust St.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (130)
"Had a wonderful time. This home was just perfect for us. Great location and charming. Would definitely stay here again"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Waterfront property with private boat ramp and new dock!
Exterior
Waterfront property with private boat ramp and new dock!
9.2 out of 10, Wonderful, (5)
"Perfect size for a small family. Nice kitchen and furnishings, very cute. Nice quiet neighborhood setting."
Waterfront property with private boat ramp and new dock!
Cottage at Goose Neck Point
Living area
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, (28)
"What a little slice of heaven. Checkin was easy peasy. Owner left a welcome basket w goodies and wine. That was a very nice gesture. The property and area is beautiful. I wish I could call it my home away from home:). The home was perfect, clean and everything the pictures showed. Just a perfect getaway to escape the craziness of life. Didn’t want to leave. "
Cottage at Goose Neck Point
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Terrace/patio
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
10.0 out of 10, Exceptional, (12)
"What a wonderful bungalow! Convenient location for Calvert Cliffs hiking, Cove Point lighthouse, PAX Naval Air Museum and Calvert Marine Museum. We really enjoyed the screened porch for relaxing and our meals. Special treat with the coffee bar. Kitchen was stocked with everything we needed. "
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Pet-friendly Annapolis Home: Walk to Beach!
Property grounds
Pet-friendly Annapolis Home: Walk to Beach!
3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Enchanting West River Retreat
View from property
Enchanting West River Retreat
10.0 out of 10, Exceptional, (5)
"The views are spectacular and the boat dock is lovely..the hospitality was amazing too can’t wait to come back and visit "
Enchanting West River Retreat
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Front and side of W Melson House
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (114)
"We love escaping to St Michaels for a change of scenery. These historic properties are great places to disconnect from our normal fast paced lifestyle. We always enjoy that our dogs are able to enjoy our stay. It’s a vacation for them as well. The town is very dog friendly in general. The properties are historic and have their quirks. For us, this adds to the experience and charm of St Michaels. The centralized location is key. "
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Updated North Beach Cottage: Pet Friendly!
North Beach Vacation Rental | 3BR | 2BA | 1,440 Sq Ft | Stairs Required to Enter
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, (10)
"We had a great time. Nice place. Within walking distance to small deli/ market. Just wished we wouldn't have had to pay to go to the beach."
Updated North Beach Cottage: Pet Friendly!
The Middle Point Cabin in Saint Michaels
Living area
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
Waterfront, cozy cottage with private pool on 27 acres of privacy
Private Pool
Waterfront, cozy cottage with private pool on 27 acres of privacy
9.8 out of 10, Exceptional, (87)
"We had a wonderful time overlooking the water and swimming in the refreshing pool while enjoying easy access to downtown Cambridge and Blackwater NW Refuge."
Waterfront, cozy cottage with private pool on 27 acres of privacy
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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 Tilghman

Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
View
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
9.4 out of 10, Exceptional, (6)
"The home was beautiful, the indoor pool was great Everything about the home was perfect for our family vacation (4generations). The only thing that was not enjoyable was the flooding caused by hurricane Debby but it did leave us with memories. . Eastern Shores is a great host and kept us informed "
Tilghman Waterfront | Indoor Pool | Private Dock | Pool House
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Grill no longer works
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Cass-Away Luxury Houseboat
Cass-Away Luxury Houseboat
10.0 out of 10, Exceptional, (87)
"All as advertised Wonderful option to a hotel"
The price is SAR 525
SAR 1,313 total
includes taxes & fees
26 Sep - 27 Sep
Cass-Away Luxury Houseboat
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.

Frequently asked questions

How much do cottages in Tilghman cost?
Cottages in Tilghman range between SAR249 and SAR249 per night. These retreats offer a chance to soak up nature’s beauty — at a price you can afford. This price was 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?
You’ll find 66 cottages in Tilghman. No matter if you’re taking a trip with the family or planning a getaway with your besties, Expedia will help you find the right space to enjoy nature’s beauty.
Why book your cottage in Tilghman with Expedia?
We think that a vacay should be hassle-free, so if you’re chasing cottages in Tilghman at an affordable rate, Expedia can help. Save cash and pick an inexpensive option far from the downtown buzz, or book an upmarket cottage to spoil your loved ones.
How can I find cheap cottages in Tilghman?
Expedia can help you locate cheap cottages in Tilghman. To reserve your dream stay in a few quick keystrokes, simply use our handy filter tool to tailor your search results by amenities, star rating and budget.