Search Eastern Shore Cottage Rentals from CA $187

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Check prices for these dates

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Aug 29 - Aug 31
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Sep 5 - Sep 7
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Sep 19 - Sep 21
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Oct 17 - Oct 19

Browse Select Eastern Shore Cottages

Our top choices for Eastern Shore cottages

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Smart TV, books

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

10.0 out of 10, Exceptional, (19)
"Very nice cottage, as advertised"
The price is CA $242
CA $286 total
includes taxes & fees
Sep 1 - Sep 2
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
6 Mi to Salisbury: Forest-view Sanctuary!
House (3 Bedrooms) | Front of property

6 Mi to Salisbury: Forest-view Sanctuary!

3.0 star property
The price is CA $140
CA $330 total
includes taxes & fees
Aug 21 - Aug 22
6 Mi to Salisbury: Forest-view Sanctuary!
Comfortable cottage in gated community, 5 mins to OC and Assateague
Outdoor pool

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

9.8 out of 10, Exceptional, (34)
"Everything was great here, and the owners were very responsive. We would definitely stay here again."
The price is CA $187
CA $500 total
includes taxes & fees
Sep 1 - Sep 2
Comfortable cottage in gated community, 5 mins to OC and Assateague
Deal Island Bay Cottage
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (57)
"We got every year and stay here, it’s great! "
The price is CA $219
CA $382 total
includes taxes & fees
Sep 10 - Sep 11
Deal Island Bay Cottage
Quarry Landing - Center of Town & River View - 3 Bedroom
Property grounds

Quarry Landing - Center of Town & River View - 3 Bedroom

9.8 out of 10, Exceptional, (7)
"Great stay in a relaxing community. We loved to be able to walk to places from the house! The hosts were very helpful and easy to communicate with 💙"
The price is CA $245
CA $368 total
includes taxes & fees
Aug 27 - Aug 28
Quarry Landing - Center of Town & River View - 3 Bedroom
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio

Grandma’s Cottage will wrap around you like a warm hug

The price is CA $311
CA $578 total
includes taxes & fees
Sep 8 - Sep 9
Grandma’s Cottage will wrap around you like a warm hug
Long Beach Cottage, (romantic couple’s getaway)
Terrace/patio

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 $586
CA $865 total
includes taxes & fees
Aug 31 - Sep 1
Long Beach Cottage, (romantic couple’s getaway)
Thunder Hill Retreat - Spacious/Deck/Hot tub
Outdoor spa tub

Thunder Hill Retreat - Spacious/Deck/Hot tub

10.0 out of 10, Exceptional, (14)
"Had a nice stay."
The price is CA $355
CA $765 total
includes taxes & fees
Sep 1 - Sep 2
Thunder Hill Retreat - Spacious/Deck/Hot tub
Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (431)
"Great place to stay!"
The price is CA $299
CA $336 total
includes taxes & fees
Sep 1 - Sep 2
Key West Cottages
Heart of Amish Country - Paradise Cottage
Terrace/patio

Heart of Amish Country - Paradise Cottage

10.0 out of 10, Exceptional, (34)
"Very comfortable with lots of extra amenities making it feel like home. "
The price is CA $184
CA $376 total
includes taxes & fees
Aug 25 - Aug 26
Heart of Amish Country - Paradise Cottage
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
On the beach

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

9.6 out of 10, Exceptional, (4)
"Just the perfect place I needed for a personal retreat. It is quiet, peaceful and serene. I would definitely visit again. "
The price is CA $250
CA $415 total
includes taxes & fees
Aug 21 - Aug 22
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (31)
"The A-frame cottage was clean and comfortable. I was accompanied by my son and two grandchildren (ages 12 and 14), and we really loved it. We went fishing in bay at the beach area below the cottage, and also did a lot of fossil hunting along the cliffs, which are breathtaking. Our host Teresa was extremely helpful and welcoming. We will definitely be going back!"
The price is CA $208
CA $434 total
includes taxes & fees
Aug 24 - Aug 25
Soul Oasis - home on the Chesapeake Bay
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Outdoor pool

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

10.0 out of 10, Exceptional, (47)
"We had a great stay! Thanks."
The price is CA $241
CA $457 total
includes taxes & fees
Aug 24 - Aug 25
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Interior

5 Mi to Downtown Baltimore: Quiet Home w/ Porch

3.0 star property
The price is CA $261
CA $656 total
includes taxes & fees
Aug 26 - Aug 27
5 Mi to Downtown Baltimore: Quiet Home w/ Porch
Charming Carriage House in the Heart of Kennett
Outdoor dining

Charming Carriage House in the Heart of Kennett

10.0 out of 10, Exceptional, (34)
"Booked and stayed it was a great little place to have while visiting family"
The price is CA $283
CA $611 total
includes taxes & fees
Sep 1 - Sep 2
Charming Carriage House in the Heart of Kennett
Cottage Located on the Patuxent River!
Sun loungers

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (39)
"The accommodations were superb and being on the water was amazing!"
The price is CA $418
CA $500 total
includes taxes & fees
Aug 21 - Aug 22
Cottage Located on the Patuxent River!
Charming off grid cottage near sports at the beach and local oceans
1 bedroom, WiFi, bed sheets

Charming off grid cottage near sports at the beach and local oceans

The price is CA $201
CA $238 total
includes taxes & fees
Sep 10 - Sep 11
Charming off grid cottage near sports at the beach and local oceans
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
Property grounds

Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock

10.0 out of 10, Exceptional, (15)
"Hubs and I were looking for a relaxing getaway and boy did we find it. This cottage was perfect. "
The price is CA $241
CA $365 total
includes taxes & fees
Sep 1 - Sep 2
Escape to the Eastern Shore -Upscale Romantic Waterfront getaway cottage w dock
Charming 1-bedroom cottage with loft in Rehoboth Beach
Interior

Charming 1-bedroom cottage with loft in Rehoboth Beach

9.6 out of 10, Exceptional, (7)
"My daughter and I spent Mother's Day weekend here and it was the perfect fit for our short getaway. Close to the beach and restaurants. Quiet. "
The price is CA $208
CA $477 total
includes taxes & fees
Aug 24 - Aug 25
Charming 1-bedroom cottage with loft in Rehoboth Beach
Cozy Spring House in Gorgeous Chadds Ford!
Outdoor dining

Cozy Spring House in Gorgeous Chadds Ford!

10.0 out of 10, Exceptional, (62)
"We were in town for a wedding nearby and this cozy cottage fit the bill for our needs. It's certainly a quirky little property, but that adds to the charm. Plenty of everything you would need for your stay."
The price is CA $275
CA $473 total
includes taxes & fees
Aug 24 - Aug 25
Cozy Spring House in Gorgeous Chadds Ford!
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

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"Staff was excellent, helpful and super friendly"
Bob 2-night trip
Posted 18 hours ago
Princess Royale Oceanfront Resort