A marina with numerous sailboats docked at wooden piers.

Eastern Maryland Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Eastern Maryland vacation rentals

A room with a large bed, multiple windows, and a ceiling fan.

1. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is ￥9,845
￥38,588 total
includes taxes & fees
Nov 5 - Nov 6
Salisbury Riverfront Lofts
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

2. Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Salisbury
9.8 out of 10, Exceptional, (25 reviews)
"Great location with plenty of space to relax."
United States
Doug R.
The price is ￥11,050
￥28,518 total
includes taxes & fees
Oct 11 - Oct 12
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A single-story house with a front porch, a door, and a mailbox.

3. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (24 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is ￥18,942
￥51,535 total
includes taxes & fees
Oct 6 - Oct 7
Salisbury Hideaway
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

4. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
The price is ￥31,254
￥66,426 total
includes taxes & fees
Nov 2 - Nov 3
Salisbury Cottage
A beachside boardwalk with shops, a Ferris wheel, and a tram.

5. On Main Street - Apartment C - Berlin, MD

On Main Street - Apartment C - Berlin, MD
Downtown Berlin
9.4 out of 10, Exceptional, (43 reviews)
"A perfect location if you want to explore downtown Berlin. It’s right in the heart of Main Street walking distance to everything.The apartment had everything we needed and was very cozy and clean . Would definitely book this spot again."
United States
Sarah V.
The price is ￥11,365
￥36,419 total
includes taxes & fees
Oct 18 - Oct 19
On Main Street - Apartment C - Berlin, MD
A gym with treadmills, dumbbells, and exercise balls, large windows with a view of the ocean.

6. Coconut Malorie Resort Ocean City, an Ascend Collection Hotel

Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
3.0 star property
Midtown Ocean City
7.4 out of 10, Good, (1,324 reviews)
"Our room.seemed to be all new and we loved how there was a separate living room and bedroom with privacy doors. We had a beautiful view of the bay too from the second floor and we loved being on the sunset side of OC:)"
United States
cara
The price is ￥14,986
￥16,784 total
includes taxes & fees
Oct 16 - Oct 17
Coconut Malorie Resort Ocean City, an Ascend Collection Hotel
A modern kitchen with dark cabinets, a white countertop, and a large window.

7. Cass-N-Reel Luxury Houseboat

Cass-N-Reel Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (51 reviews)
"Had a great time, great property and great location."
United States
Danny B.
The price is ￥14,207
￥42,356 total
includes taxes & fees
Oct 8 - Oct 9
Cass-N-Reel Luxury Houseboat
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

8. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (129 reviews)
"This property is delightful. It's very "beachy" and relaxing. There are lots of thoughtful amenities which made our stay smooth. The only thing I would mention is that the property is reached by a set of six stair steps, even though strictly speaking it is on the first floor of the house. That wasn't a problem for us. Other than that, we can highly recommend it. We thoroughly enjoyed our stay here. (My husband wants me to mention that he loved the bed and slept very well.)"
United States
Charr
The price is ￥15,627
￥25,073 total
includes taxes & fees
Oct 6 - Oct 7
First Floor Studio Apartment in Historic Chestertown
A riverside dock with boats, a covered seating area, and a bridge in the background.

9. Historic Chesapeake City Stay

Historic Chesapeake City Stay
Chesapeake City
9.2 out of 10, Wonderful, (30 reviews)
"The rental was perfect for what we needed. The bed and living room furniture were very comfortable and the kitchen well stocked. The host was quick to respond to questions I had. I will definitely see if this rental if available the next time I’m in the area."
United States
Martha J.
The price is ￥17,048
￥44,006 total
includes taxes & fees
Oct 6 - Oct 7
Historic Chesapeake City Stay
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

10. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"
United States
Harold B.
The price is ￥22,020
￥40,575 total
includes taxes & fees
Oct 6 - Oct 7
Deal Island Bay Cottage
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

11. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is ￥18,595
￥45,101 total
includes taxes & fees
Oct 6 - Oct 7
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

12. 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
9.8 out of 10, Exceptional, (29 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is ￥10,734
￥19,744 total
includes taxes & fees
Oct 6 - Oct 7
Guest Suite for up to 2 in a Victorian on the Chester River
A multi-story building with a white exterior, balconies, and a sign indicating it is an apartment complex.

13. Ocean Terrace Family Apartments

Ocean Terrace Family Apartments
3.0 star property
Downtown Ocean City
7.6 out of 10, Good, (63 reviews)
"There isn’t a lot if parking for the property but besides that it was great"
United States
Pamela
Ocean Terrace Family Apartments
A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

14. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (63 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is ￥12,786
￥29,449 total
includes taxes & fees
Oct 12 - Oct 13
Cottage near the Bay
A covered porch with wooden flooring, white railings, and two green chairs.

15. Wilmington Terrace

Wilmington Terrace
3.0 star property
Downtown Ocean City
8.2 out of 10, Very good, (12 reviews)
"The staff was very friendly, the apartment was very clean, I love that pets are welcome and the beach and boardwalk are less than 2 minutes walk. EXCELLENT!"
United States
Jennifer
The price is ￥18,440
￥33,280 total
includes taxes & fees
Oct 6 - Oct 7
Wilmington Terrace
A balcony with two chairs and a table, overlooking a beach with the ocean and a clear sky.

16. #1 Rated Condo, Oceanfront, with Bay View Too

#1 Rated Condo, Oceanfront, with Bay View Too
North Ocean City
10.0 out of 10, Exceptional, (342 reviews)
"Had a great stay "
United States
Ed B.
The price is ￥14,049
￥44,022 total
includes taxes & fees
Oct 6 - Oct 7
#1 Rated Condo, Oceanfront, with Bay View Too
A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

17. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (40 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is ￥24,467
￥39,990 total
includes taxes & fees
Oct 6 - Oct 7
Sailwinds Loft at Cambridge Creek
A spacious living room with a dining area, a ceiling fan, a TV, and a balcony with a view.

18. BeachBox II • Panoramic Inlet Views • Bayside Pool • Park Free • Couple's Corner

BeachBox II • Panoramic Inlet Views • Bayside Pool • Park Free • Couple's Corner
Downtown Ocean City
10.0 out of 10, Exceptional, (40 reviews)
"This place was super clean and had everything we needed. We will definitely be back in the summer because the location is perfect and the views from the balcony are outstanding!"
United States
Donna B.
The price is ￥8,407
￥37,859 total
includes taxes & fees
Oct 7 - Oct 8
BeachBox II • Panoramic Inlet Views • Bayside Pool • Park Free • Couple's Corner
A wooden gazebo with a table and chairs, surrounded by plants and a grill.

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

BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
Berlin
9.8 out of 10, Exceptional, (112 reviews)
"Great hosting by Laurie"
United States
Jim C.
The price is ￥31,570
￥60,640 total
includes taxes & fees
Oct 6 - Oct 7
BEACH HAVEN Assatique/Berlin Dog friendly, outside bar and kitchen
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 Bayside Beach Hotel

Princess Bayside Beach Hotel

8/10 Good
"Nice place. Great location"
Adrienne 2-night trip
Posted 1 hour ago
Princess Bayside Beach Hotel

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