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Compare 19 Cottages in Eastern Maryland with updated reviews, rates, and availability.

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (207)
"The location is ideal for traveling to several towns in the area. We did find the sleeper sofa unusable (blocked the exit too much) and the kitchenette was lacking a few expected items. However, the unit was fantastic made for a great family vacation spot. We shall return."
Shore Point Cottages

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (244)
"The only thing I can say is that the online listing really doesn’t do justice to how amazingly stunning Rob & Clarissa’s place is. My family and I decided last minute that we wanted to spend a weekend on the bay. I never expected it to be so beautiful! We got there late in the evening and we were speechless when we woke up to the most beautiful view of the water. My son had an amazing time between playing in the loft or in the playhouse outside, kayaking, and paddle boating. My parents “settled”...
Family and Pet-Friendly, Waterfront with Pier

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

9.8 out of 10, Exceptional, (177)
"Such a beautiful home-perfect location, filled with antiques plus everything needed for a fun getaway. The house is located right off of Talbott Street- enjoyed walking to local bakery/coffee shop- Sprout, eating breakfast at Carpenter Street Saloon and shopping. Great communication with our host who was so knowledgeable about the area. Church bells rang throughout the day. Beautiful views all around. Easy walk to the Lighthouse and Maritime Museum."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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

9.6 out of 10, Exceptional, (118)
"Shower was disappointing. Hard to get in and out."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

9.6 out of 10, Exceptional, (138)
"Wow! Property was great. Like steping back in time with all the amenities. Only 1 block from shops and restaurants. Just a few blocks to beautiful boats and park. Highly recommend "
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

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!

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

8.4 out of 10, Very Good, (48)
"The house was nice. Neighbor quiet. It was nice there is a small park across the street for the dog. Had everything I need in the house. It was nice I did not have to bring my own sheets and towels. They were supplied to us. The beach is a short drive up the street, maybe a minute or two and there was plenty of parking. I would stay here again if I go down to ocean city again."
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower

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

4.6 out of 10, (7)
"My family and I stayed at the Parrot Bay Condo for the first time this year. We had fun! My children enjoyed the bunk bed, and the cottage where we used to stay every summer did not have a pool, so having the 3-5 foot pool was another feature that enhanced our vacation this year. I wished I had a fly swatter because flies do get in the house, but we would stay here again if it’s available again next year. Recommended!"
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, (26)
"Very nice, clean and quiet location. Would definitely book again."
The price is ¥14,240
¥44,258 total
includes taxes & fees
May 4 - May 5
Comfortable cottage in gated community, 5 mins to OC and Assateague

Charming 2-bedroom cottage in the heart of West Ocean City

10.0 out of 10, Exceptional, (1)
The price is ¥22,499
¥46,629 total
includes taxes & fees
Apr 21 - Apr 22
Charming 2-bedroom cottage in the heart of West Ocean City

"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.

10.0 out of 10, Exceptional, (91)
"It was a lovely property that had everything our family needed. It was convenient to the shore and the local attractions."
"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.

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

9.6 out of 10, Exceptional, (114)
"The house is quaint and very clean. It could use a refresh. Can't beat the location. You can walk to everything. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Private waterfront cottage with pool on Church Creek

10.0 out of 10, Exceptional, (61)
"This was one of the most beautiful spots I've seen. Kayaking was wonderful! Couch was very uncomfortable. And many maybe put off to find they must put everything in a box to keep away from rodents. And I just took my garbage home as we didn't have time to dump at an off site location on vacation. I would still book again as it was the most peaceful, charming and secluded place to truly relax!"
Private waterfront cottage with pool on Church Creek

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (3)
"We had a wonderful time! Being near the water is my happy place. The size of the home is perfect for me. And the weather was perfect! Thank you!"
The price is ¥51,066
¥77,729 total
includes taxes & fees
May 8 - May 9
Long Beach Cottage, (romantic couple’s getaway)

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville Home w/ Private Pool on the Water

Charming Salisbury Getaway w/ Grill & Fire Pit!

3.0 star property
Charming Salisbury Getaway w/ Grill & Fire Pit!

Cottage downtown on a quiet street

9.8 out of 10, Exceptional, (59)
"My husband and I visited St. Michael’s for our 20th anniversary. This cottage was exactly what we were looking for. It is central located so we were able to walk everywhere. The cottage had everything you would need to have a fabulous stay. The town is charming and the people are just as charming and welcoming."
Cottage downtown on a quiet street

Charming 1-bedroom cottage in downtown Saint Michaels

Charming 1-bedroom cottage in downtown Saint Michaels

Waterfront St Michaels Vacation Rental w/ Fire Pit

3.0 star property
Waterfront St Michaels Vacation Rental w/ Fire Pit
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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Other property types in Eastern Maryland

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
The price is ¥8,318
¥11,603 total
includes taxes & fees
May 19 - May 20
Majestic Hotel & Apartments

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (207)
"The location is ideal for traveling to several towns in the area. We did find the sleeper sofa unusable (blocked the exit too much) and the kitchenette was lacking a few expected items. However, the unit was fantastic made for a great family vacation spot. We shall return."
Shore Point Cottages

Saint Tropez

3.0 star property
9.2 out of 10, Wonderful, (97)
"The state was absolutely amazing. Starting off with the beautiful view of the ocean. The serenity and tranquility of the establishment is well worth the trip. Minutes away from the Ocean City convention center is a plus."
The price is ¥44,002
¥48,842 total
includes taxes & fees
Apr 21 - Apr 22
Saint Tropez
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.