Search Cottages in Eastern Shore

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 26 Cottages in Eastern Shore with updated reviews, rates, and availability.

Shore Point Cottages
Deluxe Cottage | Private kitchen | Fridge, microwave, stovetop, dishwasher

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (209)
"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
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (245)
"This is a beautiful site and the hosts were incredibly welcoming and hospitable. We highly recommend it to anyone looking for a place to stay in the area."
Family and Pet-Friendly, Waterfront with Pier
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

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

9.8 out of 10, Exceptional, (179)
"Host was amazing. Property is perfect. Will be staying here again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Dog-Friendly Westover Cottage w/ River Access!
Fridge, microwave, stovetop, dishwasher

Dog-Friendly Westover Cottage w/ River Access!

9.8 out of 10, Exceptional, (10)
"Loved being right on the river. It was quiet, exactly the getaway we wanted! Very pet friendly. "
Dog-Friendly Westover Cottage w/ River Access!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

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

9.6 out of 10, Exceptional, (118)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

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

9.6 out of 10, Exceptional, (138)
"We loved this house, it was perfect for exploring town and as a base for things further afield. Comfortable, thoughtfully and well stocked with lots of charm."
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Be persuaded to experience this vintage cottage by the Sassa
Outdoor dining

Be persuaded to experience this vintage cottage by the Sassa

9.4 out of 10, Exceptional, (8)
"Had a lovely peaceful stay. Great amenities."
Be persuaded to experience this vintage cottage by the Sassa
Dog-friendly beach cottage with WiFi, W/D, updated kitchen & outdoor shower
Terrace/patio

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

8.4 out of 10, Very Good, (48)
"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
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
View from property

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

10.0 out of 10, Exceptional, (40)
"This was our 2nd time at the house and it was just as relaxing as we hoped. Nice, quiet location and beautiful home!"
Accessible, Screened-in porch, Water Access, Sauna, Fire Pit, Dog Friendly
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
Fridge, microwave, oven, stovetop

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

4.6 out of 10, (7)
"The house is small and needs updated for sure as the other reviews have stated. We did like the location, ease of checking in and out, the responsiveness of Vacasa and the porch. It was nice to have an outside space."
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower
Comfortable cottage in gated community, 5 mins to OC and Assateague
Property grounds

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

9.8 out of 10, Exceptional, (26)
"We enjoyed staying at this property. We have stayed at Assateague point several times in the past and will be back."
The price is AED 367
AED 1,166 total
includes taxes & fees
4 May - 5 May
Comfortable cottage in gated community, 5 mins to OC and Assateague
Charming 2-bedroom cottage in the heart of West Ocean City
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (1)
The price is AED 367
AED 930 total
includes taxes & fees
4 May - 5 May
Charming 2-bedroom cottage in the heart of West Ocean City
"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.

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

10.0 out of 10, Exceptional, (91)
"The VRBO was great! Clean, plenty of dishes and pots and pans for cooking. And a great location near Downtown Berlin and Assateague Island"
"Family Friendly Getaway" - Close to Assateague / Downtown Berlin / O.C.
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, (115)
"Perfect stay in a historic home in the heart of town."
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Private waterfront cottage with pool on Church Creek
Fridge, microwave, oven, stovetop

Private waterfront cottage with pool on Church Creek

10.0 out of 10, Exceptional, (61)
"Very clean, comfortable, and cozy property with gorgeous view of the water. Would definitely stay here again. Just wish we spent more time on the property this stay, but obligations in Fishing Creek kept us away most of the time. Thank you for sharing your lovely cottage!!"
Private waterfront cottage with pool on Church Creek
Long Beach Cottage, (romantic couple’s getaway)
Property grounds

Long Beach Cottage, (romantic couple’s getaway)

10.0 out of 10, Exceptional, (3)
"Loved the property and the decor. Very well done and luxurious!"
The price is AED 1,193
AED 1,858 total
includes taxes & fees
8 May - 9 May
Long Beach Cottage, (romantic couple’s getaway)
Grasonville Home w/ Private Pool on the Water
Interior

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!
House (3 Bedrooms) | Interior

Charming Salisbury Getaway w/ Grill & Fire Pit!

3.0 star property
Charming Salisbury Getaway w/ Grill & Fire Pit!
Cottage downtown on a quiet street
Marina

Cottage downtown on a quiet street

9.8 out of 10, Exceptional, (59)
"It's a very nice place and the location is great. Its not a professionally managed house which is fine, but we didn't know that going in. Everything is clean, but not professionally clean i.e. the sheets are clean but the mattress pad was not. I would stay there again."
Cottage downtown on a quiet street
Charming 1-bedroom cottage in downtown Saint Michaels
Interior

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
Basic Apartment, 2 Bedrooms, Non Smoking | Private kitchen

Majestic Hotel & Apartments

3.0 star property
6.6 out of 10, (187)
"Friendly staff and I was able to check in early. Would definitely stay here again next year!"
The price is AED 215
AED 299 total
includes taxes & fees
21 May - 22 May
Majestic Hotel & Apartments
Shore Point Cottages
Deluxe Cottage | Private kitchen | Fridge, microwave, stovetop, dishwasher

Shore Point Cottages

3.0 star property
9.4 out of 10, Exceptional, (209)
"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
Exterior

Saint Tropez

3.0 star property
9.2 out of 10, Wonderful, (98)
"It was a great place, we loved our time there, just to walk out to the beach. Would definitely recommend this place. "
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.