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

Shore Point Cottages

Shore Point Cottages

3 out of 5
9543 Stephen Decatur Hwy Berlin MD
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
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

St Michaels MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

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

Tilghman Island MD
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
Waterfront Cottage on the C&D Canal!

Waterfront Cottage on the C&D Canal!

Chesapeake City MD
At this cottage, guests have access to a garden.
Kitchen
Free WiFi
Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland

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

Charlestown MD
At this cottage, guests have access to barbecue grills.
Kitchen
Washer
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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

Saint Michaels MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Charming Cottage - Northeast River / Chesapeake Bay

Charming Cottage - Northeast River / Chesapeake Bay

Perryville MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Comfortable cottage in gated community, 5 mins to OC and Assateague

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

Berlin MD
$400 nightly
The price is $448 total per night
$448 total
Sep 1 - Sep 2
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
Waterfront Home, Private Dock, A/C, Amazing Views, Boating, Fishing & Kayaking

Waterfront Home, Private Dock, A/C, Amazing Views, Boating, Fishing & Kayaking

North East MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
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

    Princess Royale Oceanfront Resort

    Oceanfront on 91st Street Ocean City MD
    $151 nightly
    The price is $167 total per night from Sep 7 to Sep 8
    $167 total
    Sep 7 - Sep 8
    Total with taxes and fees
    8.8/10 Excellent! (2,630 reviews)
    Grand Hotel Ocean City Oceanfront

    Grand Hotel Ocean City Oceanfront

    2100 N Baltimore Ave Ocean City MD
    $154 nightly
    The price is $172 total per night from Sep 7 to Sep 8
    $172 total
    Sep 7 - Sep 8
    Total with taxes and fees
    Fenwick Inn

    Fenwick Inn

    13801 Coastal Highway Ocean City MD
    $102 nightly
    The price is $115 total per night from Sep 7 to Sep 8
    $115 total
    Sep 7 - Sep 8
    Total with taxes and fees
    8.8/10 Excellent! (2,082 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
$115
Highest Price
$448
Popular accommodation
Shore Point Cottages, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Waterfront Cottage on the C&D Canal!, Charming 2-bedroom cottage at Murphy's Beach in lovely Charlestown Maryland, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Charming Cottage - Northeast River / Chesapeake Bay, Comfortable cottage in gated community, 5 mins to OC and Assateague, Waterfront Home, Private Dock, A/C, Amazing Views, Boating, Fishing & Kayaking

More to Explore