Holiday Rentals in Barclay

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Holiday Rentals in Barclay

Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

10.0 out of 10, Exceptional, (51)
"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."
Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18.

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Guest Lodge | Private Pool | Outdoor Dining | Game Room

Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!

The price is €379
includes taxes & fees
31 Mar - 1 Apr
Modern Family Retreat – Roomy, Chic, and Close to DE Turf, Casino & the Beaches!

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

10.0 out of 10, Exceptional, (46)
"We had a wonderful time. The home is absolutely fabulous! We are already talking about when we can return. Peaceful and restorative, just what we needed. "
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Newly renovated single family home with attached guest suite

Newly renovated single family home with attached guest suite

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (32)
"Beautiful home, beautiful property! My family meets up annually and the house fit us perfectly. Plenty of room to spread out and congregate together. The home also provides so much to do with all the amenities! Thanks for the memories "
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (79)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is €155
includes taxes & fees
12 Mar - 13 Mar
First Floor Studio Apartment in Historic Chestertown

Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

10.0 out of 10, Exceptional, (55)
"The family had a lovely time. The home was beautiful and the landscape surrounding the home was magnificent. "
Stunning Waterfront Hideaway on Michener's Choptank River. Special Rates*

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (34)
"We had a wonderful weekend at Bayside Bungalow. Chris and Paul have really set up a great spot to enjoy some peace and quiet on the Chesapeake Bay. Thank you for your hospitality and attention to detail!Sincerely,J, J and L"
The price is €263
includes taxes & fees
1 Mar - 2 Mar
BAYSIDE BUNGALOW

Stylish Home on the Choptank River (with Tidal Beach)

10.0 out of 10, Exceptional, (32)
"A beautiful and serene setting mapping the contours of nature, tranquility & relaxation. Steven is an exceptional host."
Stylish Home on the Choptank River (with Tidal Beach)

Spacious 5 Bedroom w/Pool, Patio and Theater

9.6 out of 10, Exceptional, (4)
"The house had everything for our family’s stay. It was perfect even on the rainy days."
Spacious 5 Bedroom w/Pool, Patio and Theater

3 Mi to Dover Motor Speedway: Pet-Friendly Retreat

3 Mi to Dover Motor Speedway: Pet-Friendly Retreat

Newly restored apartment in the heart of Chestertown

9.8 out of 10, Exceptional, (19)
"We fell in love with Chestertown and are so glad we stayed in the heart of downtown at this charming vrbo. Everything was perfect. Will return and recommend "
Newly restored apartment in the heart of Chestertown

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (133)
"Perfect location for watching the sunsets as the house is located right across the street from the beach. Also, an easy bike ride to restaurants and shops on Main St. The house is clean and comfortable. Highly recommend to other guests!"
Eastern Shore beach cottage get-away

A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

10.0 out of 10, Exceptional, (24)
"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.

Saybrook Hall | Pickleball + Pool + Hot Tub

Saybrook Hall | Pickleball + Pool + Hot Tub

Pet-Friendly Home on Chester River w/ Dock!

2.0 star property
9.6 out of 10, Exceptional, (4)
"An absolute stunning view from the four season enclosed porch. This beautiful home is well equiped and a perfect location for Fall and Winter hunting trips near Chestertown/Kennedyville. Plenty of rooms/bathrooms/beds. Highly recommend!!!"
Pet-Friendly Home on Chester River w/ Dock!

Stay in the landmark Lighthouse!

10.0 out of 10, Exceptional, (96)
"We stayed at the light house for three nights in celebration of the new year, 2025. It was a work vacation involving winter covering of our sailboats as well as celebrating the new year. We thoroughly enjoyed our time together and will come here again."
Stay in the landmark Lighthouse!

Waterfront Home & Dock,Remodel Kitchen,Eastern shore, Betterton,Chestertown MD.

9.8 out of 10, Exceptional, (87)
"The house and location on Still Pond Maryland was great!! House was clean and tiddy. Caught perch, catfish and bass off their dock!! Area is beautiful and quiet! "
Waterfront Home & Dock,Remodel Kitchen,Eastern shore, Betterton,Chestertown MD.

Waterfront Paradise on the Eastern Shore of Chesapeake Bay

10.0 out of 10, Exceptional, (62)
"Bigger, nicer and newer than it looks in the pics; a pleasant surprise. Great location, we’d go again. "
Waterfront Paradise on the Eastern Shore of Chesapeake 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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Other types of properties in Barclay you may be interested in

Bally's Dover Casino Resort

4.0 star property
8.8 out of 10, Excellent, (2306)
"Quiet and comfortable with very accommodating service…"
The price is €83
includes taxes & fees
25 Mar - 26 Mar
Bally's Dover Casino Resort

Microtel Inn & Suites by Wyndham Dover

2.0 star property
8.0 out of 10, Very good, (1002)
"It was a amazing stay. Will stay again "
The price is €79
includes taxes & fees
12 Mar - 13 Mar
Microtel Inn & Suites by Wyndham Dover

Comfort Inn & Suites

2.5 star property
8.8 out of 10, Excellent, (1003)
"Property was good but not great "
The price is €86
includes taxes & fees
23 Mar - 24 Mar
Comfort Inn & Suites
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.

Frequently asked questions

Are there holiday rentals in Barclay?

Yes, there are holiday rentals close to the most popular sights in Barclay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Barclay has to offer?

Guest Lodge | Private Pool | Outdoor Dining | Game Room: This holiday home rental outside of Barclay is equipped with an arcade/games room, air conditioning and laundry facilities to help you feel comfortable during your stay. 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 Hazel Miner Monument, or get outside and enjoy nature at Saulsbury Road Park. Tilmon's Island Winery and Church Hill Theatre are a couple of places you'll find in the wider area.

What’s a holiday rental in Barclay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Barclay. Holiday rentals feature amenities such as patios, hot tubs and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for small groups.