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, (19)
"Great well-furnished townhouse in a great location and a super responsive host. What’s not to like?!?!"
United States
Lynn
The price is NZ$624
includes taxes & fees
8 Dec - 9 Dec
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Salisbury Cottage

Salisbury
10.0 out of 10, Exceptional, (32)
"This cottage was cute, clean, and perfect for our long weekend. Grateful for the ease of communication with the owners, which made checking in and out simple. We would certainly stay again if we’re in the area."
United States
Adina G.
The price is NZ$585
includes taxes & fees
18 Nov - 19 Nov
Salisbury Cottage

Relax on Kent Island in 3 Bedroom Home w/Waterview

Stevensville
9.8 out of 10, Exceptional, (41)
"This is a great place for a small family and friends' weekend reunion."
United States
Paul G.
The price is NZ$464
includes taxes & fees
16 Nov - 17 Nov
Relax on Kent Island in 3 Bedroom Home w/Waterview

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

Stevensville
9.6 out of 10, Exceptional, (31)
"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 NZ$425
includes taxes & fees
13 Nov - 14 Nov
❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

Berlin
10.0 out of 10, Exceptional, (99)
"Even tho we didn’t eat in. The kitchen was awesome!"
United States
Chris S.
The price is NZ$561
includes taxes & fees
30 Nov - 1 Dec
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen

Salisbury Hideaway

Salisbury
10.0 out of 10, Exceptional, (19)
"Great house and beautiful neighborhood near downtown Salisbury and the University. House was clean and well-stocked with everything we needed. Really enjoyed our stay!"
United States
Melanie M.
The price is NZ$628
includes taxes & fees
8 Dec - 9 Dec
Salisbury Hideaway

Summer Rustic Camping with AC and King Bed

Elkton
9.6 out of 10, Exceptional, (5)
"The dome and surrounding areas looks like it does in the photos, and using the compost toilet, shower, etc were pretty easy even for a camping novice like myself. The farm is beautiful and quiet. Good opportunities for birding too. I never saw or heard the gentlemen who live in the farmhouse, I only saw their cars come and go. I came here for rest and a connection to nature, and that’s what I got. I’d love to come back in the future! I think it would be even nicer later in the spring."
United States
Lady N.
The price is NZ$280
includes taxes & fees
13 Nov - 14 Nov
Summer Rustic Camping with AC and King Bed

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

Centreville
10.0 out of 10, Exceptional, (7)
"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 NZ$787
includes taxes & fees
17 Nov - 18 Nov
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Cozy Barn Loft: Country Views & Central to Beaches

Pocomoke City
10.0 out of 10, Exceptional, (19)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
The price is NZ$465
includes taxes & fees
13 Nov - 14 Nov
Cozy Barn Loft: Country Views & Central to Beaches

Beautiful Waterfront Retreat in Cambridge!

Cambridge
10.0 out of 10, Exceptional, (49)
"Wonderful stay. The Crab Shack and dock were the highlights. We spent most of our time there. It was awesome. Highly recommend. "
United States
Christopher D.
The price is NZ$707
includes taxes & fees
16 Nov - 17 Nov
Beautiful Waterfront Retreat in Cambridge!

Turnbridge Manor

Denton
9.8 out of 10, Exceptional, (12)
"We rented this wonderful home for Christmas and had the most relaxing time. The house is just as advertised and the owner a delight to work with. We especially loved the proximity to the square and how walkable it was to everything. I can’t wait to rent it again during warm weather to enjoy all the wonderful porches and the outdoor area."
United States
Katie K.
The price is NZ$1,085
includes taxes & fees
17 Nov - 18 Nov
Turnbridge Manor

Harborview Retreat Mansion

West Ocean City
10.0 out of 10, Exceptional, (2)
"Beautiful, clean and quiet community. We enjoyed our stay and would love to come back and stay again. "
United States
Mariel D.
The price is NZ$1,215
includes taxes & fees
14 Nov - 15 Nov
Harborview Retreat Mansion

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

Grasonville
9.6 out of 10, Exceptional, (12)
"I was impressed with how spacious and clean the house was."
United States
Susan M.
The price is NZ$740
includes taxes & fees
20 Nov - 21 Nov
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Ocean Pines Family Beach Retreat~Jetted Tub~King Bed~Golf 3 bd 2.5 batownhome

2.0 star property
Ocean Pines
The price is NZ$447
includes taxes & fees
13 Nov - 14 Nov
Ocean Pines Family Beach Retreat~Jetted Tub~King Bed~Golf 3 bd 2.5 batownhome

Room #3 in Elkton, MD – Easy Access to I-95

2.0 star property
Elkton
The price is NZ$234
includes taxes & fees
13 Nov - 14 Nov
Room #3 in Elkton, MD – Easy Access to I-95

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

Elkton
8.0 out of 10, Very good, (9)
"Beautiful location in the middle of Elk Neck State Park. We slept comfortably and enjoyed our stay. Heads up for travelers (esp city folk!) with small children, don’t forget the tick repellent. We found one on our son who had played in the yard for a short time. "
United States
NEB 7.
The price is NZ$497
includes taxes & fees
13 Nov - 14 Nov
Charming 3-bedroom house with WiFi, AC in peaceful Elk Neck

BeachParadise1208-Charming 4BR Townhouse•DOWNTOWN•Short walk to Beach&Boardwalk

2.0 star property
Downtown Ocean City
10.0 out of 10, Exceptional, (1)
"Great place to stay!"
United States
Joseph D.
The price is NZ$536
includes taxes & fees
20 Nov - 21 Nov
BeachParadise1208-Charming 4BR Townhouse•DOWNTOWN•Short walk to Beach&Boardwalk

Cottage near the Bay

Crisfield
8.8 out of 10, Excellent, (50)
"We had a great time! Everything went smoothly from beginning to end! We would definitely stay here again. "
United States
Jennifer J.
The price is NZ$332
includes taxes & fees
15 Nov - 16 Nov
Cottage near the Bay

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 NZ$555
includes taxes & fees
15 Nov - 16 Nov
Kayak friendly home on the Chesapeake Bay with bikes, paddle board & golf cart

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

Downtown Ocean City
10.0 out of 10, Exceptional, (17)
"Very nice property and great location. Very close to beach and multiple restaurants"
United States
Owen G.
The price is NZ$544
includes taxes & fees
13 Nov - 14 Nov
Beach Paradise X-NEW, Luxury Townhouse with POOL, Garage !!PRIME BOARDWALK!!
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