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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Relax in a serene outdoor space with a comfortable seating area and picturesque views of the surrounding forest.

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

10.0 out of 10, Exceptional, (50)
"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
Relaxing Waterfront Cottage Near St Michaels, Maryland
Escape to a serene lakeside retreat with a cozy cabin nestled among mature trees, featuring a dock and a tranquil atmosphere.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (224)
"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
Relax in a serene park setting surrounded by lush greenery and a central gazebo.

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

9.8 out of 10, Exceptional, (184)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Kitchen area with a stove, dishwasher, refrigerator, sink, and countertop with a kettle.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (103)
"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
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Boats docked at the marina, surrounded by trees and buildings.

"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
Peaceful getaway convenient to local amenities including beach, boating & food
Guests can enjoy breathtaking views of the calm body of water from the rocky outcrop.

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (115)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Surrounded by lush greenery, this charming fence features a carved stone face at its center.

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

9.8 out of 10, Exceptional, (10)
"We really enjoyed our long weekend at The Oyster Cottage. We needed some rest and relaxation and this cottage was perfect. Very well maintained and stocked! "
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Charming Waterfront Cottage Retreat near St. Michaels
Enjoy a view of the lush landscape from the kitchen window.

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (7)
"Great weekend get away if you’re just looking for some peace and quiet with some great scenery. The kitchen was immaculate and everything was as listed."
Charming Waterfront Cottage Retreat near St. Michaels
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Relax in a serene outdoor setting with a tranquil lawn and water view, perfect for a peaceful retreat.

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
Stroll along the waterfront path to a historic bench, flanked by cannons, with serene views of the calm water and boats docked at the pier.

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

9.6 out of 10, Exceptional, (121)
"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
Eastern Shore beach cottage get-away
Enjoy a serene beach experience with a gentle shoreline and peaceful surroundings.

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (136)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Enjoy serene lakeside views and moored boats, perfect for a relaxing day on the water.

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!
Enjoy waterfront views from the dock, surrounded by lush greenery and serene water.

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!
Chesapeake Cottage
1 bedroom, iron/ironing board, WiFi, bed sheets

Chesapeake Cottage

10.0 out of 10, Exceptional, (1)
"The cottage acted as the perfect base for our little weekend getaway with friends. Positioned well on Kent Island, and with plenty of parking for three sedans, it was very easy to get from place to place. The space appeared to be similar to an in-law suite, just big enough to move around while being compact and cozy. Just enough necessities were there at the cottage, including basic condiments in the fridge, cutlery, shower essentials, etc. Overall we were very happy with our stay and would...
Chesapeake Cottage
Tilghman Island Retreat By Knapps Narrows!
Interior

Tilghman Island Retreat By Knapps Narrows!

3.0 star property
Tilghman Island Retreat By Knapps Narrows!
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Interior

Waterfront Annapolis Home: Fire Pit & Fishing Pier

3.0 star property
Waterfront Annapolis Home: Fire Pit & Fishing Pier
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Interior

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

3.0 star property
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Relax by the serene pool surrounded by lush greenery and vibrant flowers.

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Charming cottage with Pool Access and WiFi in lovely Rock Hall
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Enjoy a serene lakeside retreat with a deck, perfect for outdoor dining and taking in the tranquil views.

Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills

10.0 out of 10, Exceptional, (1)
"This cottage was a great place to stay. It had everything needed for a comfortable stay. "
Charming 1BR cottage w/ WiFi, AC in wonderful Wye Mills
Grasonville Home w/ Private Pool on the Water
Relax by the serene pool overlooking the lake and enjoy the tranquil atmosphere.

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water
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 Wye Mills Hotel Reviews

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

10/10 Excellent
"Nice comfortable stay."
Thomas 2-night trip
Posted 2 days ago
Best Western Plus Easton Inn & Suites

Frequently asked questions

Why book your cottage in Wye Mills with Expedia?
Booking a cottage in Wye Mills is as simple as entering your travel dates and selecting your ideal place for a getaway in the outdoors. From upmarket retreats to budget-friendly stays and cottages that include perks like a hot tub, Expedia has something for all styles and tastes. As for terrific deals? We've have them as well!
How can I find cheap cottages in Wye Mills?
With Expedia's handy filter tool, scoring cheap cottages in Wye Mills couldn't be easier. To find properties that are very pocket friendly, fine-tune your search results by budget, amenities and star rating.
What is there to do in Wye Mills near my cottage?
Once you've settled into your hotel, get out and explore the incredible things Wye Mills has on offer. Wye Oak State Park is a top attraction to add to your travel itinerary.