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Check prices for these dates

In two weeks
3 Oct - 5 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec
In four months
9 Jan - 11 Jan

Cottages in Eastern Shore

Shore Point Cottages
Exterior

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (291)
"Great place would definitely stay again"
Shore Point Cottages
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (257)
"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
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, (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!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior

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

9.6 out of 10, Exceptional, (124)
"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
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Exterior

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (104)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Exterior

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

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

10.0 out of 10, Exceptional, (11)
"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)
Comfortable cottage in gated community, 5 mins to OC and Assateague
Exterior

Comfortable cottage in gated community, 5 mins to OC and Assateague

9.8 out of 10, Exceptional, (40)
"Everything was great here, and the owners were very responsive. We would definitely stay here again."
The price is SAR 506
SAR 1,357 total
includes taxes & fees
21 Sep - 22 Sep
Comfortable cottage in gated community, 5 mins to OC and Assateague
Waterfront property with private boat ramp and new dock!
Outdoor dining

Waterfront property with private boat ramp and new dock!

9.2 out of 10, Wonderful, (16)
"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!
Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette
Fridge, microwave, oven, dishwasher

Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette

10.0 out of 10, Exceptional, (1)
"Location and having a place to yourself was perfect for a quiet getaway weekend."
Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior

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

9.8 out of 10, Exceptional, (185)
"Excellent accommodations. Comfortable, good location.One way you could improve is to furnish wash cloths and hand towels. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Outdoor dining

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (9)
"Can’t say enough about how nice this place is. We had quick friendly responses from owners. Very clean and the water front view was excellent. Highly recommended "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Exterior

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

9.6 out of 10, Exceptional, (143)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Exterior

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (9)
"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
"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.
Exterior

"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.

10.0 out of 10, Exceptional, (103)
"Would stay again! Cute place close to EVERYTHING! "
"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Exterior

Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower

8.4 out of 10, Very Good, (54)
"The seashell cottage was a nice little place in a great location. It could easily earn 5 stars if there was more care and attention to cleaning the indoors and the exterior of the property such as the outdoor shower."
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
Exterior

Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower

8.6 out of 10, Excellent, (7)
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Exterior

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

10.0 out of 10, Exceptional, (52)
"My wife and I have stayed at many different places over the years but this may be one of the most well maintained properties I've ever seen. It was a great place for us to unwind with our dog and we would certainly recommend this location for anyone looking to stay in the area"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Outdoor pool

Charming cottage with Pool Access and WiFi in lovely Rock Hall

10.0 out of 10, Exceptional, (3)
"Wonderful 2 night stay at this charming cottage in Rock Hall. We would definitely recommend. "
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Charming cottage near the boardwalk & beach with AC, WiFi, kitchen
Fridge, microwave, oven, stovetop

Charming cottage near the boardwalk & beach with AC, WiFi, kitchen

6.0 out of 10, (2)
"Major ant problem in both bedrooms and kitchen."
Charming cottage near the boardwalk & beach with AC, WiFi, kitchen
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 Eastern Shore Hotel Reviews

Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

10/10 Excellent
"This is my favorite hotel to stay at during bike week. I trailer my bike every year and parking my car and trailer is never a problem. Thats a big plus for me. Very hassle free for the rest of my stay."
George 3-night trip
Posted 3 hours ago
Carousel Resort Hotel & Condominiums

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between SAR 1,357 and SAR 1,357 per night for cottages in Eastern Shore. No matter your budget, a fantastic stay is just clicks away on Expedia. 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.
What are the best cottages in Eastern Shore?
Eastern Shore offers multiple cottages with a total average guest review rating of 9.5. Planning a trip to Ocean City? Travelers prefer Frontier Town Campground, a 2-star property with a swimming pool and a barbecue grill. Another top pick where you can escape the hustle and bustle is 103 79th Street 3 Bedroom Cottage By Redawning. It has a 3-star rating and amenities such as a nearby beach and a patio.
How many cottages are there in Eastern Shore?
Take your pick of 26 cottages in Eastern Shore. Whether you're traveling with the whole family, as a couple or with a group of workmates, Expedia will help you find the perfect space.

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