Compare Eastern Shore Cottage Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Cottages in Eastern Shore

At Shore Point Cottages, guests have access to a seasonal outdoor pool, laundry facilities, and a vending machine. A stay here includes free parking.

Pool

Kitchen

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

$426 nightly

$477 total

Jul 13 - Jul 14

Total with taxes and fees

Guests staying at this cottage enjoy an outdoor pool, an arcade/game room, and laundry facilities. This family-friendly cottage also has a garden.

Pool

Kitchen

Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland

At this cottage, guests have access to barbecue grills.

Washer

Dryer

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

At this cottage, guests have access to features like laundry facilities.

Kitchen

Washer

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

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills. Helpful staff is there to provide concierge services, as well as offer insight about the area.

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

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.

Kitchen

Washer

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.

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

Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.

Pool

Kitchen

Charming Cottage - Northeast River / Chesapeake Bay

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.

Don't see what you're looking for?

See all available properties in Eastern Shore

View all properties

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.

Hotel Options in Eastern Shore

Princess Royale Oceanfront Resort

Oceanfront on 91st Street Ocean City MD

$329 nightly

$366 total

Aug 2 - Aug 3

Total with taxes and fees

8.8/10 Excellent! (2,533 reviews)

Grand Hotel Ocean City Oceanfront

2100 N Baltimore Ave Ocean City MD

$309 nightly

$346 total

Jul 12 - Jul 13

Total with taxes and fees

9/10 Wonderful! (3,680 reviews)

Howard Johnson by Wyndham Ocean City Oceanfront

2401 Atlantic Ave Ocean City MD

$328 nightly

$367 total

Jul 12 - Jul 13

Total with taxes and fees

8.8/10 Excellent! (1,022 reviews)

Cottages

Book a cottage in Eastern Shore
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Eastern Shore. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Eastern Shore better.

Cottage apartments in Eastern Shore range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Eastern Shore
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Eastern Shore and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Eastern Shore cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Eastern Shore. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Eastern Shore Cottages essential information

Accommodation	27 Cottages
Lowest Price	$346
Highest Price	$477
Popular accommodation	Shore Point Cottages, Comfortable cottage in gated community, 5 mins to OC and Assateague, Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE, "Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C., John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Charming Cottage - Northeast River / Chesapeake Bay