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Barclay Vacation Rentals

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Our top choices for Barclay vacation rentals

1. 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 $312
CA $488 total
includes taxes & fees
Aug 30 - Aug 31
Newly restored apartment in the heart of Chestertown

2. 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 price is CA $94
CA $173 total
includes taxes & fees
Sep 14 - Sep 15
Guest Suite for up to 2 in a Victorian on the Chester River

3. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store
Hartly
The price is CA $143
CA $211 total
includes taxes & fees
Aug 30 - Aug 31
Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

4. 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 $444
CA $690 total
includes taxes & fees
Aug 30 - Aug 31
Wren Retweet- Country Estate in Center of C’Town

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 $388 total
includes taxes & fees
Sep 2 - Sep 3
Secluded Cottage in Middle of Chestertown

6. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (124 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is CA $137
CA $220 total
includes taxes & fees
Sep 2 - Sep 3
First Floor Studio Apartment in Historic Chestertown

7. 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 $425
CA $534 total
includes taxes & fees
Sep 23 - Sep 24
Family Retreat at Lansdowne Manor

8. 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 $399 total
includes taxes & fees
Sep 14 - Sep 15
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

9. 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 $138
CA $227 total
includes taxes & fees
Sep 11 - Sep 12
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.

10. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $250
CA $401 total
includes taxes & fees
Sep 11 - Sep 12
BAYSIDE BUNGALOW

11. Mini Aruba RV/Glamping Tent

Mini Aruba RV/Glamping Tent
Dover
10.0 out of 10, Exceptional, (6 reviews)
"We had an absolutely wonderful stay at this adorable glamping camper oasis while in town for the NASCAR All-Star Race weekend. The camper and property were spotless, beautifully maintained, and it has so many thoughtful amenities that made our stay comfortable and relaxing.The heated pool was amazing after a long day, and the entire atmosphere was peaceful, welcoming, and fun. The hosts were incredibly friendly, gracious, and accommodating throughout our stay. You can truly tell they take...
United States
Roberta J.
The price is CA $208
CA $339 total
includes taxes & fees
Sep 6 - Sep 7
Mini Aruba RV/Glamping Tent

12. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (16 reviews)
"Really nice place and you can walk to everything.Will stay again!"
United States
Glenn S.
The price is CA $499
CA $856 total
includes taxes & fees
Sep 9 - Sep 10
Turnbridge Manor

13. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (27 reviews)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
United States
Max G.
The price is CA $312
CA $519 total
includes taxes & fees
Aug 31 - Sep 1
Waterfront Retreat with Private Dock and Beach

14. 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, (28 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $164
CA $397 total
includes taxes & fees
Aug 30 - Aug 31
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

15. 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

16. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is CA $250
CA $506 total
includes taxes & fees
Sep 29 - Sep 30
Bayside Cottage steps from Rock Hall Harbor

17. 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

18. Cozy Room in Dover

Cozy Room in Dover
Dover
The price is CA $81
CA $133 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Room in Dover
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 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?

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining: This vacation home rental near Barclay is located near the beach and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Turner's Creek 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.