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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Eastern Maryland and around

Shore Point Cottages
Enjoy cooking in this well-equipped kitchen with a stainless steel sink, microwave, and oven.

Shore Point Cottages

3.0 star property
9.2 out of 10, Wonderful, (276)
"Great place would definitely stay again"
Shore Point Cottages
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Stroll along the waterfront path to a historic bench, flanked by cannons, with serene views of the calm water and boats docked at the pier.

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
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!
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Stylish entrance with a wooden staircase and a mailbox.

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)
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Relax in a serene park setting surrounded by lush greenery and a central gazebo.

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

9.8 out of 10, Exceptional, (184)
"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
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, (2)
"Major ant problem in both bedrooms and kitchen."
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, (253)
"Our stay was great and Rob and Clarissa were very welcoming!"
Family and Pet-Friendly, Waterfront with Pier
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, oven, sink, and coffee maker.

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

8.4 out of 10, Very good, (6)
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
Comfortable cottage in gated community, 5 mins to OC and Assateague
Relax by the pool surrounded by lounge chairs and umbrellas.

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

9.8 out of 10, Exceptional, (33)
"The property is lovely! It is well-kept & very clean & stocked with everything that you will need for your time away from home. The location is perfect as well; short drive to OC & Assateague. "
The price is €334
includes taxes & fees
1 Sept - 2 Sept
Comfortable cottage in gated community, 5 mins to OC and Assateague
Ocean block cottage nestled steps away from OC shoreline FREE LINENS
Cozy living space with a kitchenette, dining area, and comfortable seating area featuring a sofa and armchairs.

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
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Enjoy serene lakeside views and moored boats, perfect for a relaxing day on the water.

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
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Enjoy waterfront views from the dock, surrounded by lush greenery and serene water.

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!
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Relax in style on this inviting patio, complete with a wicker table and comfortable seating.

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!
Enjoy casual dining and relaxation in this inviting kitchen area with a central island and stools.

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!
Waterfront beach cottage w/ full kitchen, cable, free WiFi - close to the beach
Enjoy casual meals and gatherings in this kitchen with a large island, dining area, and essential appliances.

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

6.8 out of 10, (17)
"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
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!"
Long Beach Cottage, (romantic couple’s getaway)
Charming Salisbury Getaway w/ Grill & Fire Pit!
Kitchen features a central island with a bowl for food preparation, white cabinetry, microwave, and oven, along with two stools for seating.

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!
Enjoy cooking in this well-lit kitchen with stainless steel appliances, white cabinetry, and granite countertops.

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

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"My husband has always avoided OC MD like the plague. He was pleasantly surprised and changed his outlook because of this hotel! I could not stop asking if we could come back! The staff were kind and very accommodating! "
Alicia 2-night trip
Posted 1 day ago
Grand Hotel Ocean City Oceanfront

Frequently asked questions

How much do cottages in Eastern Maryland cost?
Cottages in Eastern Maryland range between €334 and €334 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 travelling 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 travelling 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.