Barclay Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Barclay vacation rentals

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is CA $96
CA $165 total
includes taxes & fees
Nov 9 - Nov 10
Guest Suite for up to 2 in a Victorian on the Chester River
A kitchen with a wooden island, built-in cabinets, and a window providing a view of the outdoors.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is CA $278
CA $389 total
includes taxes & fees
Nov 16 - Nov 17
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

3. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (133 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is CA $140
CA $212 total
includes taxes & fees
Nov 9 - Nov 10
First Floor Studio Apartment in Historic Chestertown
A garden path leading to a wooden building with a rustic appearance.

4. 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 $257
CA $386 total
includes taxes & fees
Nov 18 - Nov 19
Secluded Cottage in Middle of Chestertown
A kitchen with wooden cabinets, a dining table, and a refrigerator.

5. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 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 $325
CA $374 total
includes taxes & fees
Nov 8 - Nov 9
Family Retreat at Lansdowne Manor
A room with a wooden bench, a vase with flowers, and a door leading to an outdoor area with trees.

6. 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
10.0 out of 10, Exceptional, (12 reviews)
"Nice clean place. Highly recommended."
United States
Richard B.
The price is CA $134
CA $214 total
includes taxes & fees
Nov 29 - Nov 30
Woodland Hideaway: Cozy 1 bedroom apartment tucked away in a quiet neighborhood.
A spacious living area with a dining table, sofa, and a kitchen in the background.

7. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is CA $315
CA $451 total
includes taxes & fees
Nov 12 - Nov 13
Newly restored apartment in the heart of Chestertown
A covered porch with a wooden bench, potted plants, and a decorative railing.

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 $430
CA $616 total
includes taxes & fees
Nov 8 - Nov 9
Wren Retweet- Country Estate in Center of C’Town
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

9. Turtle Cove Room

Turtle Cove Room
Kent County
10.0 out of 10, Exceptional, (1 review)
"The host was very communicative. The room was clean. It was quiet and peaceful. There were blackout curtains on the windows. A very pleasant stay."
United States
Jennifer M.
The price is CA $229
CA $269 total
includes taxes & fees
Nov 9 - Nov 10
Turtle Cove Room
A two-story house with a porch, two windows, and a door.

10. Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD

Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
Denton
10.0 out of 10, Exceptional, (15 reviews)
"The house was perfect, welcoming and comfortable, will be coming back again"
United States
Dallas S.
The price is CA $318
CA $496 total
includes taxes & fees
Dec 1 - Dec 2
Quiet Farmhouse on 4 acres, 2 Bedroom, close to town, Denton MD
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

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 $246
CA $281 total
includes taxes & fees
Nov 9 - Nov 10
Beachcomber Suite
A house with a blue front door, two windows, and a small porch.

12. 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, (33 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is CA $188
CA $411 total
includes taxes & fees
Nov 22 - Nov 23
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A building with a gabled roof and a circular vent on the roof.

13. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is CA $280
CA $422 total
includes taxes & fees
Nov 9 - Nov 10
BAYSIDE BUNGALOW
A modern kitchen with white cabinets, stainless steel appliances, and a marble island with bar stools.

14. 5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover

5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
Dover
10.0 out of 10, Exceptional, (5 reviews)
"Host was great"
United States
mark o.
The price is CA $338
CA $842 total
includes taxes & fees
Nov 20 - Nov 21
5 Minutes from Bally’s Casino, Charming 3-bed 2-bath Ranch in Dover
A modern kitchen with a large island, bar stools, and pendant lighting.

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

Spacious 5 Bedroom w/Pool, Patio and Theater
Magnolia
9.2 out of 10, Wonderful, (12 reviews)
"The host was very accommodating and the house was excellent and served our needs perfectly."
United States
John K.
The price is CA $388
CA $941 total
includes taxes & fees
Nov 9 - Nov 10
Spacious 5 Bedroom w/Pool, Patio and Theater
A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

16. Turnbridge Manor

Turnbridge Manor
Denton
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful home. Plenty of space inside with great outdoor spaces. Very clean and easy to contact host. Family friendly-would highly recommend!"
United States
Jessica H.
The price is CA $509
CA $830 total
includes taxes & fees
Nov 9 - Nov 10
Turnbridge Manor
A covered outdoor seating area with a wooden ceiling, two chairs, a table, and a wicker sofa.

17. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is CA $252
CA $490 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
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.
View all properties

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
Cottage image
Cottages
Cottages

Top Barclay Hotel Reviews

A hotel lobby with a fireplace, seating area, and a television.
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown

10/10 Excellent

Bon service
Canada
Sébastien
Reviewed August 22, 2026
Comfort Inn & Suites Chestertown

Find out more about Barclay

Everything you need to know about Barclay vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Barclay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Barclay vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Barclay vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Barclay. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Barclay vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Barclay vacation rentals we have selected for you start as low as CA $96 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Barclay rentals

At Expedia, we put the best Barclay vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Barclay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Barclay vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Barclay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*: This vacation home near Barclay is located on a river and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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.