Holiday Homes in Eastern Shore

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Featured Holiday Homes in Eastern Shore

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cambridge
9.6 out of 10, Exceptional, (20)
"In town for a family wedding. This worked out perfectly. Would stay there again "
United States
Barbara V.
The price is AU$544
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Salisbury Cottage

Salisbury
10.0 out of 10, Exceptional, (33)
"Very clean, great communication and fabulous location close to SU!"
United States
Anne M.
The price is AU$502
includes taxes & fees
10 Dec - 11 Dec
Salisbury Cottage

Salisbury Hideaway

Salisbury
10.0 out of 10, Exceptional, (19)
"This property was wonderful for our trip to Salisbury for my daughter's travel softball tournament. It was only 30-45 minutes from Ocean City (give or take traffic), and very close to many shopping areas and restaurants. The property itself was very clean and provided many necessities. "
United States
Lisa H.
The price is AU$488
includes taxes & fees
9 Dec - 10 Dec
Salisbury Hideaway

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville
9.6 out of 10, Exceptional, (32)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is AU$378
includes taxes & fees
9 Dec - 10 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville
9.8 out of 10, Exceptional, (42)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is AU$386
includes taxes & fees
11 Dec - 12 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Cottage near the Bay

Crisfield
8.8 out of 10, Excellent, (52)
"Srea was quiet, peaceful, plenty of information provided about the area restaurants, grocery stores, etc. Enjoyed our stay."
United States
Darla J M.
The price is AU$287
includes taxes & fees
9 Dec - 10 Dec
Cottage near the Bay

Summer Rustic Camping with AC and King Bed

Elkton
9.6 out of 10, Exceptional, (5)
"The owners were very attentive to our needs, and everything was exactly as advertised. We came up for a horse show in Maryland and the convenience to the grounds was exceptional, and everything was wonderful from the privacy to the beauty of the property."
United States
Rees L.
The price is AU$240
includes taxes & fees
9 Dec - 10 Dec
Summer Rustic Camping with AC and King Bed

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Beautiful place! Loved all the activities, will return in the future! Our family and friends had a blast! Thank you so much!!"
United States
Karen L.
The price is AU$577
includes taxes & fees
10 Dec - 11 Dec
Beautiful Waterfront Retreat in Cambridge!

Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

Smith Island
9.8 out of 10, Exceptional, (15)
"The perfect place to wind down, reconnect with people, culture and a way of life we’ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much. "
United States
David
The price is AU$527
includes taxes & fees
16 Dec - 17 Dec
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is AU$678
includes taxes & fees
15 Dec - 16 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Downtown Ocean City
10.0 out of 10, Exceptional, (17)
"All amenities available, perfect location and plenty of room for a large group. Would stay again!"
United States
Trish K.
The price is AU$468
includes taxes & fees
9 Dec - 10 Dec
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$637
includes taxes & fees
9 Dec - 10 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

2.0 star property
Snow Hill
10.0 out of 10, Exceptional, (2)
"The hosts were wonderful, the house is beautiful, access & location was perfect. Next time I'm in the area & this place is avaliable, this is where I want to stay again. I recommend this house if you're in the area!!!Thanks to The Smiths"
United States
Sadat J.
The price is AU$291
includes taxes & fees
9 Dec - 10 Dec
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

OC/Fenwick Island Townhouse with Pool!

North Ocean City
9.6 out of 10, Exceptional, (11)
"Perfect location, the house is very convenient and practical. We were 15 and slept comfortably. The host communicated quickly and answered any questions we had. "
United States
Sheyla L.
The price is AU$1,257
includes taxes & fees
9 Dec - 10 Dec
OC/Fenwick Island Townhouse with Pool!

Newly Remodeled Condo - Steps to Beach & Boardwalk

Downtown Ocean City
9.8 out of 10, Exceptional, (9)
"Beautiful condo and so close to the beach!"
United States
Kathryn L.
The price is AU$741
includes taxes & fees
9 Dec - 10 Dec
Newly Remodeled Condo - Steps to Beach & Boardwalk

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$460
includes taxes & fees
1 Jan - 2 Jan 2026
BAYSIDE BUNGALOW

5-bedroom vacation home 5 minutes from historic Charlestown

Perryville
9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
The price is AU$915
includes taxes & fees
10 Dec - 11 Dec
5-bedroom vacation home 5 minutes from historic Charlestown

Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Elkton
8.0 out of 10, Very good, (10)
"Nice and quiet place to stay"
United States
Gary M.
The price is AU$428
includes taxes & fees
9 Dec - 10 Dec
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

Turnbridge Manor

Denton
9.8 out of 10, Exceptional, (12)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is AU$988
includes taxes & fees
29 Dec - 30 Dec
Turnbridge Manor

Steps to the Beach : Sea Loft 103:

North Ocean City
10.0 out of 10, Exceptional, (3)
"Too many lockboxes and under the step was a little deceiving due to finding the key on the pole right outside the door. Otherwise this was a great place and perfect location. "
United States
Kris K.
The price is AU$653
includes taxes & fees
27 Dec - 28 Dec
Steps to the Beach : Sea Loft 103:
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

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Eastern Shore Holiday Homes information

Number of reviews
521
Accommodation
632 Holiday Homes
Lowest Price
AU$240
Highest Price
AU$1,257

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