Search Cottages in Eastern Maryland

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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 27 Cottages in Eastern Maryland with updated reviews, rates, and availability.

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

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (217)
"Nice quiet property that is clean amd well kept."
Shore Point Cottages
Chesapeake Romantic Waterfront Home with Private Pool
Interior

Chesapeake Romantic Waterfront Home with Private Pool

8.8 out of 10, Excellent, (5)
"Great communication, easy to access, accommodations true to listing. Spacious, renovated living space. Great outdoor pool."
Chesapeake Romantic Waterfront Home with Private Pool
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
"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, (91)
"The VRBO was great! Clean, plenty of dishes and pots and pans for cooking. And a great location near Downtown Berlin and Assateague Island"
"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.
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

10.0 out of 10, Exceptional, (1)
The price is AED 580
AED 1,203 total
includes taxes & fees
8 Jun - 9 Jun
Charming 2-bedroom cottage in the heart of West Ocean City
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)
"Host was amazing. Property is perfect. Will be staying here again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
New to VRBO! Cozy cottage close to everything!
Fridge, microwave, oven, stovetop

New to VRBO! Cozy cottage close to everything!

10.0 out of 10, Exceptional, (1)
"We had a great trip. The house was in the perfect location. Close to shopping, restaurants, and the beach made for the perfect vacation."
New to VRBO! Cozy cottage close to everything!
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, (118)
"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
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
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
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
1 Mi to Outlets Ocean City: Home w/ Large Yard!
House (3 Bedrooms) | Front of property

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!
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 AED 744
AED 1,617 total
includes taxes & fees
5 Jun - 6 Jun
Comfortable cottage in gated community, 5 mins to OC and Assateague
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, (116)
"Perfect stay in a historic home in the heart of town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Boho chic modern 1-bedroom cottage with AC, WiFi in the heart of West Ocean City
Exterior detail

Boho chic modern 1-bedroom cottage with AC, WiFi in the heart of West Ocean City

10.0 out of 10, Exceptional, (1)
"This place was perfect! Accommodations were fantastic. Communication with owner (Karen) was fast and efficient. Could not have asked for a better place to stay while in Ocean City for a work project. Thank you! Hope to come back on next project."
The price is AED 746
AED 1,411 total
includes taxes & fees
4 Jun - 5 Jun
Boho chic modern 1-bedroom cottage with AC, WiFi in the heart of West Ocean City
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Property grounds

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

10.0 out of 10, Exceptional, (2)
"Great little cottage, beautiful scenery, quiet and peaceful. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
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
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
Grasonville Home w/ Private Pool on the Water
Interior

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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Frequently asked questions

How much do cottages in Eastern Maryland cost?
Cottages in Eastern Maryland range between AED 580 and AED 746 per night. These retreats offer a chance to reconnect with nature — at a price you can afford. 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 Maryland?
You can pick from 27 cottages in Eastern Maryland. Whether you’re traveling with your family, as a duo or with a group of friends, Expedia can help you secure your ideal digs.
Why book your cottage in Eastern Maryland with Expedia?
We think that traveling should be easy, so if you’re after cottages in Eastern Maryland at a great price, Expedia is here to help. Keep the budget under control and choose an economical option far from the rush of the city, or book a luxury cottage to spoil the ones you love most.