Search Eastern Shore Cottage Rentals from CA $206

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Aug 15 - Aug 17
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Browse Select Eastern Shore Cottages

Shore Point Cottages
Stylish mobile homes line Shore Point Lane, each with a charming porch and covered outdoor area.

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
Traditional home with a gabled roof and central chimney, set amidst a peaceful grassy lawn and trees.

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
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Outdoor dining

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (7)
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Waterfront property with private boat ramp and new dock!
Sit and enjoy the view from this shaded patio with a round table and two chairs.

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!
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Overlooking the water, this property offers a balcony with a view of the surrounding trees and a distant bridge.

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (11)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Enjoy a peaceful outdoor space with a table, chairs, and umbrella, surrounded by a tree and scenic views.

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
Enjoy a patio surrounded by lush trees and a well-manicured lawn.

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
Eastern Shore beach cottage get-away
Cozy home with a front porch and bench, surrounded by well-maintained hedges and a sandy area.

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (136)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away
Charming cottage near the boardwalk & beach with AC, WiFi, kitchen
Enjoy cooking in this well-equipped kitchen with a gas stove, oven, and refrigerator.

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
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Relax on the front porch with a bench and two chairs, surrounded by a serene garden and a wooded area.

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

10.0 out of 10, Exceptional, (50)
"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
Family and Pet-Friendly, Waterfront with Pier
Escape to a serene forest retreat with a cozy cabin-style lodge featuring a sheltered front porch and breathtaking natural views.

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
Stunning two-story home with a covered porch and garden area.

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
Pet-Friendly Smith Island Cottage w/ Golf Cart!
A small, single-story building with a gabled roof, surrounded by a white picket fence and a paved walkway.

Pet-Friendly Smith Island Cottage w/ Golf Cart!

10.0 out of 10, Exceptional, (17)
"The island is a beautiful and peaceful. Everyone there is so friendly and helpful. The cottage was a very clean and comfortable place to stay. We had 3 adults and 2 huskies and the home was very spacious. It is close to the docks, restaurant, and grocery store. We enjoyed our stay. If you’re looking for a peaceful and relaxing getaway this is the place to go! "
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Comfortable cottage in gated community, 5 mins to OC and Assateague
Exterior

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 CA $206
CA $522 total
includes taxes & fees
Sep 1 - Sep 2
Comfortable cottage in gated community, 5 mins to OC and Assateague
Ocean block cottage nestled steps away from OC shoreline FREE LINENS
Residential area with a mix of modern and traditional buildings, featuring balconies and flat roofs.

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
Traditional two-story house with a gabled roof and chimney, featuring a front entrance with a door and small porch.

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!
Relax in a serene lakeside setting with two Adirondack chairs.

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
Charming single-story house with a yard featuring a variety of plants and a birdcage.

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
Waterfront beach cottage w/ full kitchen, cable, free WiFi - close to the beach
Two lakeside houses with decks and white railings sit on a tranquil waterfront, surrounded by trees and shrubs.

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
Waterfront Cottage on the C&D Canal!
Situated lakeside, this charming property features a two-story building with a white picket fence and vibrant flowers.

Waterfront Cottage on the C&D Canal!

8.0 out of 10, Very good, (5)
"Fantastic location "
Waterfront Cottage on the C&D Canal!
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

Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"Very cute hotel right on the boardwalk. perfect if you’re looking to be on the beach "
alicia 2-night trip
Posted 20 hours ago
Grand Hotel Ocean City Oceanfront