Eastern Maryland Holiday Rentals

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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Eastern Maryland holiday rentals

View from room

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
Exterior

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, (1,299 reviews)
"We had a really lovely time and the staff was incredibly helpful with all our needs to the music festival we were in town for."
United States
Dana
The price is HK$597
HK$762 total
includes taxes & fees
1 Mar - 2 Mar
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Outdoor pool

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 HK$780
HK$2,499 total
includes taxes & fees
2 Feb - 3 Feb
Comfortable cottage in gated community, 5 mins to OC and Assateague
Beach nearby

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 HK$562
HK$1,817 total
includes taxes & fees
1 Feb - 2 Feb
On Main Street - Apartment C - Berlin, MD
Front of property

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is HK$718
HK$2,006 total
includes taxes & fees
6 Feb - 7 Feb
6 Mi to Salisbury: Forest-view Sanctuary!
Fridge, microwave, oven, stovetop

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

Quarry Landing - Center of Town & River View - 3 Bedroom
Port Deposit
10.0 out of 10, Exceptional, (11 reviews)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is HK$1,039
HK$1,639 total
includes taxes & fees
3 Feb - 4 Feb
Quarry Landing - Center of Town & River View - 3 Bedroom
Exterior

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 HK$530
HK$976 total
includes taxes & fees
4 Feb - 5 Feb
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

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 HK$546
HK$868 total
includes taxes & fees
11 Feb - 12 Feb
Country Get Away 1 Bedroom Apartment
Exterior

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

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Port Deposit
10.0 out of 10, Exceptional, (35 reviews)
"Very secluded quaint cottage. Lovely space. Great overnight getaway. Port Deposit was just a few minutes drive. Will definitely stay again! "
United States
Tim R.
The price is HK$1,369
HK$1,633 total
includes taxes & fees
31 Jan - 1 Feb
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
2 bedrooms, individually decorated, individually furnished

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 HK$543
HK$1,971 total
includes taxes & fees
2 Feb - 3 Feb
Salisbury Riverfront Lofts
Smart TV

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 HK$936
HK$1,257 total
includes taxes & fees
30 Jan - 31 Jan
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Property grounds

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 HK$772
HK$1,239 total
includes taxes & fees
2 Feb - 3 Feb
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop

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 HK$1,088
HK$2,014 total
includes taxes & fees
2 Feb - 3 Feb
Deal Island Bay Cottage
Interior

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (34 reviews)
"House is fabulous very clean host are very responsive Great location Attended the annual Seagull Century and super convenient to the university Would definitely stay again Group from Pittsburgh "
United States
Donald T.
The price is HK$969
HK$2,581 total
includes taxes & fees
11 Feb - 12 Feb
Salisbury Cottage
Fridge, microwave, oven, stovetop

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (19 reviews)
"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 HK$1,162
HK$2,175 total
includes taxes & fees
1 Mar - 2 Mar
Cozy Barn Loft: Country Views & Central to Beaches
Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.6 out of 10, Exceptional, (20 reviews)
"Very clean, and very comfortable beds."
United States
Edward R.
The price is HK$1,092
HK$2,704 total
includes taxes & fees
2 Feb - 3 Feb
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Marina

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20 reviews)
"This place was very cute and clean, also convenient to Shaefers Marina. It was a perfect place for us to spend a weekend on the bay. "
United States
Benay N.
The price is HK$842
HK$2,166 total
includes taxes & fees
30 Jan - 31 Jan
Historic Chesapeake City Stay
Marina

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Downtown Cambridge
9.8 out of 10, Exceptional, (12 reviews)
"This was such a cozy, comfortable space for a girls weekend away. We loved the charm of the old building paired with thoughtful amenities. "
United States
Lauren V.
The price is HK$1,053
HK$2,663 total
includes taxes & fees
2 Feb - 3 Feb
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Private kitchen

Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (24 reviews)
"What a great place to relax after exploring and enjoying the area. Definitely will visit again "
United States
Chris S.
The price is HK$1,209
HK$1,984 total
includes taxes & fees
30 Jan - 31 Jan
Sailwinds Loft at Cambridge Creek
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
The price is HK$1,365
HK$2,438 total
includes taxes & fees
11 Feb - 12 Feb
Waterfront Retreat with Private Dock and Beach
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 Maryland Hotel Reviews

Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"Absolutely perfect "
Joann 1-night trip
Posted 4 days ago
Princess Royale Oceanfront Resort

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