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Compare 27 Cottages in Wye Mills 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
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
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
Eastern Shore beach cottage get-away
Early morning crabbing with Bay Bridge 12 miles away over the water.
Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (130)
"It's a great property, exactly as described. I love Rock Hall, and this location is perfect for enjoying the beach and boats, looking forward to returning again! "
Eastern Shore beach cottage get-away
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
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
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Property grounds
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (96)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown
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
Peaceful getaway convenient to local amenities including beach, boating & food
Cottage In Town
Peaceful getaway convenient to local amenities including beach, boating & food
9.8 out of 10, Exceptional, (108)
"Bay Haven was in a great lication and property mananger was very responsive to al my questions. "
Peaceful getaway convenient to local amenities including beach, boating & food
Cozy, unique, historic registered cottage on the Corsica River!
Exterior
Cozy, unique, historic registered cottage on the Corsica River!
10.0 out of 10, Exceptional, (5)
"Lovely property, cool history beautiful decor"
Cozy, unique, historic registered cottage on the Corsica River!
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Outdoor seating area just off the kitchen.
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
10.0 out of 10, Exceptional, (5)
"My friend and I wanted to meet up part way between our two cities, and when we decided on the Chesapeake Bay, Rock Hall seemed a good option, and we were right! What a great little town, and the house was just perfect for us. She brought her two little ones (6 and 2), and I was on my own. I think with just 1 bathroom, many more than that would really not be ideal. The whole stay was great, we both agreed we'd love to come back again. The only hiccup (and I am sure it will be fixed), was that...
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Terrace/patio
Waterfront Annapolis Home: Fire Pit & Fishing Pier
3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
Exterior
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
8.6 out of 10, Excellent, (10)
"This was our second visit to Bayburst Lodge and it was even better than our first! We spent an entire week this time and it really was relaxing and quite enjoyable. We did a lot of fishing this trip. We caught huge catfish off the beach behind the house, and also did a 4 hour charter in which we caught our limit in Striped Bass. The weather was incredible and we spent a lot of time walking, shopping, and sitting on the screened porch. We tried a new restaurant called Ark and Dove this trip....
Waterfront and Wonderful! Welcome to the Bayburst Lodge.
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Exterior
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
3.0 star property
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Grasonville Home w/ Private Pool on the Water
Pool
Grasonville Home w/ Private Pool on the Water
3.0 star property
Grasonville Home w/ Private Pool on the Water
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Outdoor dining
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful home. Very nice and quiet neighborhood on the water. "
The price is SAR 1,873
SAR 3,793 total
includes taxes & fees
24 Oct - 25 Oct
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
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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 Wye Mills

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
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Living area
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
10.0 out of 10, Exceptional, (17)
"This house was located so convenient after coming across the bridge. The location was easy to find and so quiet and peaceful. The house was super clean and furnished nicely. The property was beautiful. Adam was a great host and I would highly recommend this vrbo. "
The price is SAR 232
SAR 911 total
includes taxes & fees
24 Sep - 25 Sep
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️
Waterfront Cottage on the Eastern Shore
Exterior
Waterfront Cottage on the Eastern Shore
9.6 out of 10, Exceptional, (7)
"We rented the house for the weekend and to host a surprise birthday party. We had the party right at the beach and the host/concierge were able to help us with everything we needed. They really went out of their way for us, and it made a huge difference in the party’s success! Plus, you can’t beat the view and the Chesapeake Bay sunsets !!"
The price is SAR 1,310
SAR 3,073 total
includes taxes & fees
1 Oct - 2 Oct
Waterfront Cottage on the Eastern Shore
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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