Search Eastern Shore Cottage Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jun 27 - Jun 29
In two weeks
Jul 4 - Jul 6
In one month
Jul 18 - Jul 20
In two months
Aug 15 - Aug 17

Cottages in Eastern Shore

Shore Point Cottages
Deluxe Cottage | Private kitchen | Fridge, microwave, stovetop, dishwasher

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (230)
"Love the this place nice and peaceful. "
Shore Point Cottages
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
View from property

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

10.0 out of 10, Exceptional, (44)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
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, (181)
"A clean, comfortable getaway house, walking distance to St. Michaels and marinas, and well appointed."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Chesapeake Romantic Waterfront Home with Private Pool
Interior

Chesapeake Romantic Waterfront Home with Private Pool

9.0 out of 10, Wonderful, (6)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
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, (4)
"A few local spots to eat were great in the morning especially the Tighlman Market! Market has all you need to stock up with groceries and is just 2 minutes from the house."
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (247)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
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, (119)
"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
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
Interior

Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG

10.0 out of 10, Exceptional, (22)
"Close to beach and shopping"
Ocean block cottage nestled steps away from OC shoreline FREE LINEN & TOWEL PKG
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels

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

9.8 out of 10, Exceptional, (110)
"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
Waterfront, cozy cottage with private pool on 27 acres
Beach nearby

Waterfront, cozy cottage with private pool on 27 acres

9.8 out of 10, Exceptional, (88)
"Great property and the owners were gracious hosts."
Waterfront, cozy cottage with private pool on 27 acres
"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.

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

10.0 out of 10, Exceptional, (92)
"It was a lovely property that had everything our family needed. It was convenient to the shore and the local attractions."
"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Sun loungers, beach towels

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (99)
"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
Cute cottage near the boardwalk & bay with patio, outdoor shower, & kitchenette
Fridge, microwave, coffee/tea maker, toaster

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
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, (138)
"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Private waterfront cottage with pool on Church Creek
Fridge, microwave, oven, stovetop

Private waterfront cottage with pool on Church Creek

10.0 out of 10, Exceptional, (61)
"Very clean, comfortable, and cozy property with gorgeous view of the water. Would definitely stay here again. Just wish we spent more time on the property this stay, but obligations in Fishing Creek kept us away most of the time. Thank you for sharing your lovely cottage!!"
Private waterfront cottage with pool on Church Creek
Comfortable cottage in gated community, 5 mins to OC and Assateague
Property grounds

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

9.8 out of 10, Exceptional, (28)
"We enjoyed staying at this property. We have stayed at Assateague point several times in the past and will be back."
The price is ￥29,292
￥64,788 total
includes taxes & fees
Jun 25 - Jun 26
Comfortable cottage in gated community, 5 mins to OC and Assateague
1 Mi to Outlets Ocean City: Home w/ Large Yard!
House (3 Bedrooms) | Interior

1 Mi to Outlets Ocean City: Home w/ Large Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"My family and i will return to enjoy the yard which we couldn't due to the weather.. we are from the shore so the home felt like home to us😊"
1 Mi to Outlets Ocean City: Home w/ Large Yard!
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, (117)
"Perfect stay in a historic home in the heart of town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Charming 2-bedroom cottage in the heart of West Ocean City
Fridge, microwave, oven, stovetop

Charming 2-bedroom cottage in the heart of West Ocean City

9.0 out of 10, Wonderful, (2)
"Very nice cottage and some good restaurants near by"
The price is ￥25,933
￥51,174 total
includes taxes & fees
Jun 20 - Jun 21
Charming 2-bedroom cottage in the heart of West Ocean City
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Terrace/patio

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

8.4 out of 10, Very Good, (48)
"This house is in a great location. Quiet, friendly neighbors, and a large park right across the street for the dogs. We would definitely stay there again."
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

How much do cottages in Eastern Shore cost?
Prepare to pay between ￥14,610 and ￥70,589 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.
How many cottages are there in Eastern Shore?
Take your pick of 30 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.
Why book your cottage in Eastern Shore with Expedia?
Booking a cottage in Eastern Shore is as easy as deciding on your travel dates and picking your ideal place for a getaway in the outdoors. From luxurious retreats to budget-friendly stays and cottages that feature amenities like a kitchenette, Expedia has something for all traveler tastes. As for unbeatable deals? We've have them as well!