Default HTG hotel image

Barclay Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Barclay vacation rentals

1. 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, (27 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 CA $94
CA $173 total
includes taxes & fees
Sep 16 - Sep 17
Guest Suite for up to 2 in a Victorian on the Chester River

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (125 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $137
CA $220 total
includes taxes & fees
Sep 14 - Sep 15
First Floor Studio Apartment in Historic Chestertown

3. Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
Dover
9.8 out of 10, Exceptional, (10 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is CA $152
CA $242 total
includes taxes & fees
Sep 21 - Sep 22
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

4. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is CA $262
CA $397 total
includes taxes & fees
Oct 5 - Oct 6
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

5. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is CA $254
CA $381 total
includes taxes & fees
Sep 13 - Sep 14
Secluded Cottage in Middle of Chestertown

6. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is CA $311
CA $489 total
includes taxes & fees
Sep 13 - Sep 14
Newly restored apartment in the heart of Chestertown

7. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"My son and I had a great stay here for the weekend, camper was clean and had everything we needed and the family was happy to join us or let us have our privacy. All you could ask for and the backyard pool area is as good as it looks in the pictures. Would go back anytime we are in the area."
United States
Robert N.
The price is CA $219
CA $355 total
includes taxes & fees
Sep 25 - Sep 26
Mini Aruba RV/Glamping Tent

8. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is CA $421
CA $666 total
includes taxes & fees
Sep 14 - Sep 15
Wren Retweet- Country Estate in Center of C’Town

9. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is CA $459
CA $577 total
includes taxes & fees
Sep 30 - Oct 1
Family Retreat at Lansdowne Manor

10. 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 CA $163
CA $394 total
includes taxes & fees
Sep 13 - Sep 14
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

11. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is CA $221
CA $270 total
includes taxes & fees
Sep 14 - Sep 15
Beachcomber Suite

12. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is CA $81
CA $133 total
includes taxes & fees
Sep 16 - Sep 17
Cozy Room in Dover

13. Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $194
CA $241 total
includes taxes & fees
Sep 14 - Sep 15
Turtle Cove Room

14. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
The price is CA $242
CA $437 total
includes taxes & fees
Oct 4 - Oct 5
Waterfront Retreat with Private Dock and Beach

15. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (64 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $249
CA $402 total
includes taxes & fees
Sep 23 - Sep 24
BAYSIDE BUNGALOW

16. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is CA $498
CA $855 total
includes taxes & fees
Sep 14 - Sep 15
Turnbridge Manor

17. Spacious 5 Bedroom w/Pool, Patio and Theater

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.4 out of 10, Exceptional, (11 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
The price is CA $477
CA $1,084 total
includes taxes & fees
Sep 13 - Sep 14
Spacious 5 Bedroom w/Pool, Patio and Theater

18. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is CA $314
CA $590 total
includes taxes & fees
Sep 28 - Sep 29
Bayside Cottage steps from Rock Hall Harbor
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Barclay Hotel Reviews

Find out more about Barclay

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 Barclay. 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.

Frequently asked questions

Are there vacation rentals in Barclay?

Yes, there are vacation rentals close to popular sights in Barclay, or you can choose a secluded option if you're looking for relaxation.

What are some of the best vacation rentals in Barclay?

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach: Located near Barclay, this vacation home rental is located on a river and has a garden, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Barclay?

While exploring the area, visit family-friendly sights like Crumpton Auction, or get outside and enjoy nature at Saulsbury Road Park. Rolphs Wharf Marina and Chestertown Historic District are a couple of places you'll find in the larger area.

What’s a vacation rental in Barclay like?

A vacation rental is a private property you can stay in for a few weeks or just a few days in Barclay. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for a family trip.