Search Eastern Shore Cottage Rentals from CA $187

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Browse Select Eastern Shore Cottages

Shore Point Cottages

3.0 star property
9.2 out of 10, Wonderful, (282)
"The location is great."
Shore Point Cottages

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (255)
"It is a perfect spot to relax and enjoy the water. We will book again if we are back that way. "
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, (184)
"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (7)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

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

9.6 out of 10, Exceptional, (122)
"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

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

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

9.8 out of 10, Exceptional, (36)
"Everything was great here, and the owners were very responsive. We would definitely stay here again."
The price is CA $187
CA $499 total
includes taxes & fees
Sep 1 - Sep 2
Comfortable cottage in gated community, 5 mins to OC and Assateague

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!

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!

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

10.0 out of 10, Exceptional, (51)
"Beautiful home with LOTS of attention to detail. The backyard was a beautiful oasis and we LOVED the “swing bed” on the screened-in porch. Mark and Karen add lots of fine touches to make your stay special. Plenty of room for two, cozy for four, and comfortable for four legged friends with the fenced in back yard. Quiet and private with a short 10 minute drive to town. Can’t wait to return!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (10)
"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

8.6 out of 10, Excellent, (7)
Dog-friendly cottage with pool, full kitchen, AC, porch, & outdoor shower

Ocean block cottage nestled steps away from OC shoreline FREE LINENS

9.8 out of 10, Exceptional, (23)
"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

8.2 out of 10, Very good, (50)
"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

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

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 CA $333
CA $559 total
includes taxes & fees
Aug 25 - Aug 26
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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Top Eastern Shore Hotel Reviews