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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Featured Cottages in Eastern Maryland

Shore Point Cottages
Exterior

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
Exterior

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!
Outdoor dining

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
Fridge, microwave, oven, stovetop

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
Exterior

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)
Outdoor dining

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
Exterior

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 NZ$640
includes taxes & fees
2 Sept - 3 Sept
Comfortable cottage in gated community, 5 mins to OC and Assateague
Ocean block cottage nestled steps away from OC shoreline FREE LINENS
Exterior

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
Exterior

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!
Exterior

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
Exterior

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
Exterior

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
Exterior

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
Exterior

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!
Property grounds

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)
Property grounds

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 NZ$1,288
includes taxes & fees
31 Aug - 1 Sept
Long Beach Cottage, (romantic couple’s getaway)
Charming Salisbury Getaway w/ Grill & Fire Pit!
Exterior

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!
Exterior

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

Dunes Suites Oceanfront

Dunes Suites Oceanfront

10/10 Excellent
"The staff and Suite was wonderful"
Melissa 4-night trip
Posted 9 hours ago
Dunes Suites Oceanfront

Frequently asked questions

How much do cottages in Eastern Maryland cost?
Cottages in Eastern Maryland range between NZ$640 and NZ$1,288 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 24 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.
What is there to do in Eastern Maryland near my cottage?
There are plenty of exciting attractions to explore when travelling through Eastern Maryland. If you're planning a couple of days in Seaford, Williams Pond Park is a must-see.