Eastern Maryland Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Eastern Maryland vacation rentals

Deluxe Cottage | Private kitchen | Fridge, microwave, stovetop, toaster
Shore Point Cottages

Shore Point Cottages

Shore Point Cottages
3.0 star property
Berlin
9.4 out of 10, Exceptional, (301)
"Was a great place to bring kids and dogs! "
United States
AMANDA
Shore Point Cottages
Outdoor pool
Comfortable cottage in gated community, 5 mins to OC and Assateague

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)
"This was the perfect little home for our stay. Everything was clean and comfortable and “cozy”. The location was wonderful with easy access to both Assateague Island and Ocean City. Everything needed for a great stay was provided. We are already planning our vacation for next year and will definitely book again. "
United States
Alecia C.
The price is ￥14,091
￥47,793 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Comfortable cottage in gated community, 5 mins to OC and Assateague
Marina
Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD

Station House East: Upscale Loft in the Historic District Cambridge, MD
Downtown Cambridge
10.0 out of 10, Exceptional, (7)
The price is ￥9,159
￥39,582 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Station House East: Upscale Loft in the Historic District Cambridge, MD
Exterior
Coconut Malorie Resort Ocean City, Ascend Collection Hotel

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, (1297)
"Scenic area with wonderful wooden bridges and view of water. There was no hot water to shower, but not a deal breaker."
United States
Isolda
The price is ￥11,976
￥15,293 total
includes taxes & fees
Jan 28 - Jan 29, 2026
Coconut Malorie Resort Ocean City, Ascend Collection Hotel
Property grounds
Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment

Country Get Away 1 Bedroom Apartment
Elkton
9.8 out of 10, Exceptional, (40)
"Absolutely love the accommodations. First impression when entering room was so fresh and clean."
United States
Beverly M.
The price is ￥10,960
￥17,426 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Country Get Away 1 Bedroom Apartment
Apartment D: Riverfront Grand | In-room dining
Salisbury Riverfront Lofts

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (23)
"It was a great stay nice comfortable place "
United States
Adam
The price is ￥11,921
￥40,691 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Salisbury Riverfront Lofts
Marina
Historic Chesapeake City Stay

Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.0 out of 10, Wonderful, (20)
"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 ￥12,682
￥38,669 total
includes taxes & fees
Dec 30 - Dec 31
Historic Chesapeake City Stay
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

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
2.0 star property
Elkton
9.8 out of 10, Exceptional, (8)
"Great stay. Everything you need, quiet and clean. "
United States
Melissa J.
The price is ￥18,788
￥25,226 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is ￥10,647
￥19,584 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Guest Suite for up to 2 in a Victorian on the Chester River
House (3 Bedrooms) | Outdoor dining
6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is ￥14,404
￥40,266 total
includes taxes & fees
Dec 30 - Dec 31
6 Mi to Salisbury: Forest-view Sanctuary!
Smart TV, books
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

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, (33)
"The River Cottage is very charming, cozy, and well-stocked with all the essentials. The host is quick to respond to inquiries. We had a wonderful and relaxing stay!"
United States
Xiaodong F.
The price is ￥27,478
￥32,446 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Smart TV
On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (28)
"We loved everything about our stay! This place is adorable and the location is awesome!"
United States
kelly K.
The price is ￥11,273
￥35,454 total
includes taxes & fees
Jan 1 - Jan 2, 2026
On Main Street - Apartment C - Berlin, MD
Property grounds
Quarry Landing - Center of Town & River View - 3 Bedroom

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)
"Was a great stay would definitely stay again "
United States
jerel p.
The price is ￥23,172
￥36,180 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Quarry Landing - Center of Town & River View - 3 Bedroom
Marina
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City 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)
"The place was wonderful beautiful views of harbor, extremely clean and well appointed. Great restaurants we ate at RAR, great beer and food. Christopher’ Corner great dinner food fabulous and cocktails, highly recommend. Blackwater Cafe wonderful breakfast. "
United States
deb j.
The price is ￥21,920
￥54,768 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Property grounds
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews

Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
North Ocean City
9.6 out of 10, Exceptional, (93)
"Nice place. Great views"
United States
Jill M.
The price is ￥15,344
￥68,996 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Top-Rated Luxury Oceanfrt Condo Spectacular Views-Outstanding Reviews
Fridge, microwave, oven, stovetop
Deal Island Bay Cottage

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is ￥24,895
￥43,981 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Deal Island Bay Cottage
Marina
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
2.0 star property
Downtown Cambridge
9.8 out of 10, Exceptional, (11)
"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 ￥22,703
￥55,764 total
includes taxes & fees
Jan 14 - Jan 15, 2026
The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is ￥15,500
￥24,869 total
includes taxes & fees
Dec 30 - Dec 31
First Floor Studio Apartment in Historic Chestertown
Fridge, microwave, oven, stovetop
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City

Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
2.0 star property
Chesapeake City
9.4 out of 10, Exceptional, (3)
"House clean ac work great on hot weekends. Great bike path near by and nice restaurants by and the river was great on bike . Not to far from Dover for race I would stay again "
United States
Wayne
The price is ￥28,183
￥52,445 total
includes taxes & fees
Dec 30 - Dec 31
Cozy 2-bedroom apartment close to Canal Bike Trail in wonderful Chesapeake City
Dining
Cottage near the Bay

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (52)
"Great little place "
United States
Eric R.
The price is ￥12,682
￥29,375 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cottage near the Bay
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

Park Place Hotel

Park Place Hotel

10/10 Excellent
"Staff was very friendly! Room was great! "
Amanda 1-night trip
Posted 1 day ago
Park Place Hotel

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