Barclay Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Barclay

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

10.0 out of 10, Exceptional, (6)
"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (43)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is NZ$502
includes taxes & fees
3 Aug - 4 Aug
BAYSIDE BUNGALOW

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (91)
"Very pretty location. Few minutes drive to town center."
The price is NZ$267
includes taxes & fees
4 Aug - 5 Aug
First Floor Studio Apartment in Historic Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

10.0 out of 10, Exceptional, (5)
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (102)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown

Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

9.8 out of 10, Exceptional, (13)
"We loved the property and the excellent way the owners took care of it"
Dog-friendly townhouse with enclosed backyard, grill, streaming, fireplace, AC

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (22)
"I stayed with 3 friends and it was lovely! The apartment was clean and tidy. The view was spectacular. The host was very communicative and kind leading up to and during our stay. There are great restaurants and things to do in the area as well. "
The price is NZ$629
includes taxes & fees
4 Aug - 5 Aug
Waterfront Retreat with Private Dock and Beach

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

9.8 out of 10, Exceptional, (9)
"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."
The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

HGTV quality, private guest suite, country getaway with hot tub & fire pit

10.0 out of 10, Exceptional, (6)
"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "
The price is NZ$748
includes taxes & fees
4 Aug - 5 Aug
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (10)
"Perfection"
The price is NZ$492
includes taxes & fees
4 Aug - 5 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (36)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio

Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

10.0 out of 10, Exceptional, (2)
"My husband and I stayed for two nights. The oasis makes you feel like you’re vacationing in the Caribbean. The camper is clean and comfortable for two people. Everything was perfect and cannot wait to return!"
The price is NZ$396
includes taxes & fees
7 Aug - 8 Aug
Mini Aruba Glamper inDover with WiFi, AC and guest access to backyard oasis

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (83)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

10.0 out of 10, Exceptional, (9)
"It was a great vacation, the house and grounds were spectacular, the amenities, pool, kayaks, were great, and host couldn’t have been more accommodating or approachable, highly recommend in the future, hope to go back"
Waterfront oasis, tranquil masterpiece for relaxing and recreating beautifully

Peaceful living just outside of town

9.8 out of 10, Exceptional, (7)
"We really enjoyed our time there! The children enjoyed the playground set. We truly recommend! We are so grateful. Thank you! "
Peaceful living just outside of town

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (72)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Gorgeous Creek Side Ranch-Style Estate With Dock

9.8 out of 10, Exceptional, (8)
"We were in town for a family wedding and throughly enjoyed our stay at this beautiful house. The property is gorgeous and the house has everything you need to make your stay enjoyable. We will definitely be back when visiting family in the area. "
The price is NZ$1,431
includes taxes & fees
3 Aug - 4 Aug
Gorgeous Creek Side Ranch-Style Estate With Dock

Riverfront Denton Estate on 7 Acres w/ Fire Pit!

2.0 star property
10.0 out of 10, Exceptional, (9)
"The property is a great place to get away and enjoy some time with family. We enjoyed swimming in the pool. Fishing was fun as well catfish for days. Nice sunsets by the fire and just overall a great time with the family. "
Riverfront Denton Estate on 7 Acres w/ Fire Pit!

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

10.0 out of 10, Exceptional, (54)
"Great location with a great view."
Waterfront w/private pier, pool, Hot Tub, kayaks and in town.
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

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?

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets: This holiday home rental outside of Barclay is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a microwave and a coffee maker, so that 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 Hazel Miner Monument, or get outside and enjoy nature at Chestertown Dog Park. Tilmon's Island Winery and Cassinelli Winery and Vineyards 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.