Search Eastern Shore Cottage Rentals from CA $139

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Browse Select Eastern Shore Cottages

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, (245)
"This was the perfect location and property for our family. I only wished we booked a longer trip! The amenities inside and out, and the friendliness of our hosts made this a great way to relax away from the Beltway and get out on the water. The kids didn’t want to leave "
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, (179)
"I have stayed in almost every hotel and Vrbo is St Michael’s and this is my favorite house. The screen porch is a dream and there is plenty of space for my family. Just dreamy."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Dog-Friendly Westover Cottage w/ River Access!

9.8 out of 10, Exceptional, (10)
"Overall very good. Bath/shower needs upgrade Gas fireplace hard to start. May need maintenance Very pet friendly. Dog bowls, bed, and toys on site Owner allowed early arrival and was responsive quickly to any questions that we had "
Dog-Friendly Westover Cottage w/ River Access!

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

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...
Be persuaded to experience this vintage cottage by the Sassa

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

Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (40)
"We loved our stay. The house was spotless; Mark and Karen have provided everything one could possibly need, and they were super responsive. We enjoyed the porch, sauna, and fire pit; and our dog enjoyed the fully fenced backyard, nearby hikes, and dog-friendly local restaurants. Highly recommend!"
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly

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 CA $139
CA $432 total
includes taxes & fees
May 19 - May 20
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 CA $219
CA $454 total
includes taxes & fees
Apr 28 - Apr 29
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 CA $497
CA $757 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
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 Shore

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Great apartment "
The price is CA $81
CA $113 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, (98)
"We love waking up to the ocean views in a quiet area"
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.