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Check prices for these dates

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Aug 8 - Aug 10
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Aug 15 - Aug 17
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Aug 29 - Aug 31
In two months
Sep 26 - Sep 28

Cottages in Eastern Maryland

Shore Point Cottages
Stylish mobile homes line Shore Point Lane, each with a charming porch and covered outdoor area.

Shore Point Cottages

3.0 star property
9.2 out of 10, Wonderful, (273)
"Great place would definitely stay again"
Shore Point Cottages
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Enjoy a patio surrounded by lush trees and a well-manicured lawn.

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

9.8 out of 10, Exceptional, (183)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Waterfront property with private boat ramp and new dock!
Sit and enjoy the view from this shaded patio with a round table and two chairs.

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"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!
Charming cottage near the boardwalk & beach with AC, WiFi, kitchen
Enjoy cooking in this well-equipped kitchen with a gas stove, oven, and refrigerator.

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

6.0 out of 10, (1)
"No vents in bedrooms , major ant problem in rooms and kitchen, door wouldn’t lock. "
Charming cottage near the boardwalk & beach with AC, WiFi, kitchen
Family and Pet-Friendly, Waterfront with Pier
Escape to a serene forest retreat with a cozy cabin-style lodge featuring a sheltered front porch and breathtaking natural views.

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (252)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Enjoy a peaceful outdoor space with a table, chairs, and umbrella, surrounded by a tree and scenic views.

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

10.0 out of 10, Exceptional, (7)
"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)
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
Stunning two-story home with a covered porch and garden area.

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

8.6 out of 10, Excellent, (4)
"We enjoyed our stay at Parrot Bay. The decor was perfect for the beach and it had all of the amenities we needed. We liked the coffee machine, televisions in the bedrooms and living room, and cozy furniture. It was a short walk to the boardwalk, and the pool was a nice bonus!"
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
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, (33)
"We enjoyed staying at this property. We have stayed at Assateague point several times in the past and will be back."
The price is ￥22,110
￥55,792 total
includes taxes & fees
Sep 1 - Sep 2
Comfortable cottage in gated community, 5 mins to OC and Assateague
Ocean block cottage nestled steps away from OC shoreline FREE LINENS
Residential area with a mix of modern and traditional buildings, featuring balconies and flat roofs.

Ocean block cottage nestled steps away from OC shoreline FREE LINENS

10.0 out of 10, Exceptional, (22)
"Close to beach and shopping"
Ocean block cottage nestled steps away from OC shoreline FREE LINENS
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Charming single-story house with a yard featuring a variety of plants and a birdcage.

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

8.4 out of 10, Very Good, (49)
"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
New to VRBO! Cozy cottage close to everything!
Stroll up the concrete driveway to this serene two-story home, surrounded by lush lawns and mature trees.

New to VRBO! Cozy cottage close to everything!

10.0 out of 10, Exceptional, (5)
"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
Traditional home with a gabled roof and central chimney, set amidst a peaceful grassy lawn and trees.

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

9.6 out of 10, Exceptional, (121)
"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
Great for Groups: Bayside Resort Home w/ Patio
Two-story house with a symmetrical facade and manicured lawn.

Great for Groups: Bayside Resort Home w/ Patio

3.0 star property
10.0 out of 10, Exceptional, (1)
"Everything was excellent. The place was beautiful very comfortable spacious awesome place."
Great for Groups: Bayside Resort Home w/ Patio
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Traditional two-story house with a gabled roof and chimney, featuring a front entrance with a door and small porch.

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

9.6 out of 10, Exceptional, (142)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Waterfront beach cottage w/ full kitchen, cable, free WiFi - close to the beach
Two lakeside houses with decks and white railings sit on a tranquil waterfront, surrounded by trees and shrubs.

Waterfront beach cottage w/ full kitchen, cable, free WiFi - close to the beach

6.6 out of 10, (16)
"Very quiet, private location, beautiful sunset views over the bay. The house itself is very pleasant, but be aware that the steps up to the second floor bedroom are extremely steep. Do not allow young children to sleep up there."
Waterfront beach cottage w/ full kitchen, cable, free WiFi - close to the beach
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Relax in a serene lakeside setting with two Adirondack chairs.

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

9.6 out of 10, Exceptional, (118)
"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Long Beach Cottage, (romantic couple’s getaway)
Relax on the deck overlooking the calm water, surrounded by a potted plant and a comfortable sofa.

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
The price is ￥78,887
￥111,797 total
includes taxes & fees
Aug 31 - Sep 1
Long Beach Cottage, (romantic couple’s getaway)
Charming Salisbury Getaway w/ Grill & Fire Pit!
Stunning two-story home with a charming front porch and covered entryway, set amidst a beautifully manicured lawn.

Charming Salisbury Getaway w/ Grill & Fire Pit!

3.0 star property
Charming Salisbury Getaway w/ Grill & Fire Pit!
Waterfront Home w/ Hot Tub in Bozman Village!
House (4 Bedrooms) | Interior

Waterfront Home w/ Hot Tub in Bozman Village!

3.0 star property
Waterfront Home w/ Hot Tub in Bozman Village!
Updated Home - Walk to Salisbury University!
Stroll up to this charming home, featuring a cozy front porch and a beautifully manicured lawn.

Updated Home - Walk to Salisbury University!

3.0 star property
Updated Home - Walk to Salisbury University!
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 Maryland Hotel Reviews

Coastal Palms Inn & Suites

Coastal Palms Inn & Suites

10/10 Excellent
"My family and I had a great 5 days here!! Room was perfect and ALL of the staff were friendly and helpful! The lady at the front desk who does the breakfast was so sweet! She went above and beyond! We love the location to the beach and we had the perfect side view of the ocean!! "
Richelle 3-night trip
Posted 1 day ago
Coastal Palms Inn & Suites

Frequently asked questions

How much do cottages in Eastern Maryland cost?
Cottages in Eastern Maryland range between ￥22,110 and ￥78,887 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 23 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.