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Featured Cottages in Eastern Maryland

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

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!

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)

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

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

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

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

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

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 AU$586
includes taxes & fees
7 Sept - 8 Sept
Comfortable cottage in gated community, 5 mins to OC and Assateague

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

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!

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

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!

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

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)

10.0 out of 10, Exceptional, (4)
"Loved the property and the decor. Very well done and luxurious!"
The price is AU$1,179
includes taxes & fees
31 Aug - 1 Sept
Long Beach Cottage, (romantic couple’s getaway)

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!

3.0 star property
Waterfront Home w/ Hot Tub in Bozman Village!

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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Frequently asked questions

How much do cottages in Eastern Maryland cost?
Rates for cottages in Eastern Maryland range between AU$586 and AU$1,179 per night. Whatever your budget, you'll find an ideal place to relax and reconnect with nature. This price was 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?
Explore our 23 cottages in Eastern Maryland and lock in your favourite. Whether you're taking off on a family trip or a break with friends, your perfect stay is clicks away with Expedia.
What is there to do in Eastern Maryland near my cottage?
Whether you're into shopping, sightseeing, relaxation or adventure, Eastern Maryland offers it all, and then some! The awesome city of Ocean City has tons of attractions and activities, including Ocean City Beach, Seacrets Distilling Company and Trimpers Rides. If you're holidaying in Berlin, Globe Theatre, Main Street Berlin and The Bay Club will fill up your itinerary.