Eastern Shore Vacation Rentals

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Our top choices for Eastern Shore vacation rentals

Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (303 reviews)
"The location of shore point cottages is a pleasant and peaceful one. It's far enough out of the hustle and bustle of the boardwalk area. Yet close enough to everything that makes Ocean City a fun place to visit. Definitely a place to come back to and stay again."
United States
Mike
Shore Point Cottages

Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Coconut Malorie Resort Ocean City, Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,300 reviews)
"Everything was great :) Great location...great staff!"
United States
Daria
The price is CA $105
CA $134 total
includes taxes & fees
Mar 10 - Mar 11
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (23 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is CA $95
CA $345 total
includes taxes & fees
Feb 9 - Feb 10
Salisbury Riverfront Lofts

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40 reviews)
"The accommodation description is good; the actual accommodations are great, better than expected, truly a quiet country getaway with many unexpected extras. Deciding to stay here was great decision. It's done right."
United States
John L.
The price is CA $96
CA $152 total
includes taxes & fees
Feb 16 - Feb 17
Country Get Away 1 Bedroom Apartment

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.2 out of 10, Wonderful, (29 reviews)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is CA $98
CA $316 total
includes taxes & fees
Feb 9 - Feb 10
On Main Street - Apartment C - Berlin, MD

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

Comfortable cottage in gated community, 5 mins to OC and Assateague
Assateague Pointe
9.8 out of 10, Exceptional, (43 reviews)
"great place, great location, safe secure and everything we needed to get to assateague where the rest of the family were camping"
United States
Thomas B.
The price is CA $137
CA $433 total
includes taxes & fees
Feb 15 - Feb 16
Comfortable cottage in gated community, 5 mins to OC and Assateague

Guest Suite for up to 2 in a Victorian on the Chester River

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (19 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is CA $93
CA $171 total
includes taxes & fees
Feb 9 - Feb 10
Guest Suite for up to 2 in a Victorian on the Chester River

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"Yes she was welcoming "
United States
Garry B.
The price is CA $148
CA $383 total
includes taxes & fees
Feb 12 - Feb 13
Historic Chesapeake City Stay

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is CA $126
CA $352 total
includes taxes & fees
Feb 20 - Feb 21
6 Mi to Salisbury: Forest-view Sanctuary!

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo
Downtown Ocean City
9.8 out of 10, Exceptional, (62 reviews)
"Great location walking distance to everything. Thank you so much for a great stay."
United States
valerie0472
The price is CA $62
CA $479 total
includes taxes & fees
Feb 9 - Feb 10
Beach Paradise IV-Downtown Waterfront, Top Floor, Luxury Penthouse Condo

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.6 out of 10, Exceptional, (32 reviews)
"Great stay, would do it again."
United States
Brandon D.
The price is CA $140
CA $400 total
includes taxes & fees
Feb 17 - Feb 18
Charming Coastal/Country Home w/3 Acres & Sauna!

Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway

Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway
North Ocean City
10.0 out of 10, Exceptional, (18 reviews)
"The condo is beautifully decorated and only steps from the beach! "
United States
Pamela H.
The price is CA $101
CA $308 total
includes taxes & fees
Feb 9 - Feb 10
Oceanside Haven -Steps to Sand + Indoor Pool + Game Rm - Perfect Beach Getaway

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Elkton
9.8 out of 10, Exceptional, (8 reviews)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is CA $164
CA $220 total
includes taxes & fees
Feb 9 - Feb 10
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is CA $191
CA $354 total
includes taxes & fees
Feb 9 - Feb 10
Deal Island Bay Cottage

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is CA $135
CA $217 total
includes taxes & fees
Feb 9 - Feb 10
First Floor Studio Apartment in Historic Chestertown

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (17 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $161
CA $392 total
includes taxes & fees
Feb 9 - Feb 10
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Love Above the Waves - Best Ocean View & Heated Pool

Love Above the Waves - Best Ocean View & Heated Pool
North Ocean City
9.6 out of 10, Exceptional, (42 reviews)
"We enjoyed our stay. The place was nice and the view was awesome. "
United States
Ryan W.
The price is CA $163
CA $319 total
includes taxes & fees
Feb 9 - Feb 10
Love Above the Waves - Best Ocean View & Heated Pool

Summer Rustic Camping with AC and King Bed

Summer Rustic Camping with AC and King Bed
Elkton
9.6 out of 10, Exceptional, (5 reviews)
"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 CA $101
CA $212 total
includes taxes & fees
Feb 9 - Feb 10
Summer Rustic Camping with AC and King Bed

Cozy Corner: Relax on an Amish Equestrian Farm

Cozy Corner: Relax on an Amish Equestrian Farm
Rising Sun
8.8 out of 10, Excellent, (3 reviews)
"We had a very nice stay at the farmhouse, it is an incredibly clean and well cared for property. We were in town for a fishing tournament with our truck/boat and there was plenty of room for parking as well. If you’re looking for a peaceful retreat, this is a great place!"
United States
Amy C.
The price is CA $134
CA $340 total
includes taxes & fees
Feb 12 - Feb 13
Cozy Corner: Relax on an Amish Equestrian Farm

Ocean calling & country concert availability!

Ocean calling & country concert availability!
North Ocean City
9.0 out of 10, Wonderful, (35 reviews)
"Perfect place to stay for oceans calling! On bus route but not in the craziness of the direct festival area."
United States
Jennifer F.
The price is CA $86
CA $283 total
includes taxes & fees
Feb 9 - Feb 10
Ocean calling & country concert availability!
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

Find out more about Eastern Shore

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Eastern Shore. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.