Chatham Holiday Rentals

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Holiday Rentals in Chatham

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1872)
"Very nice places "
Vacation Village in the Berkshires

Postcard Cabins Eastern Catskills

2.0 star property
9.0 out of 10, Wonderful, (30)
"Great place "
The price is NZ$367
includes taxes & fees
14 July - 15 July
Postcard Cabins Eastern Catskills

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (947)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is NZ$300
includes taxes & fees
27 July - 28 July
Jiminy Peak Mountain Resort

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (121)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (106)
"We had an excellent stay, and would certainly book this place again!"
The price is NZ$234
includes taxes & fees
14 July - 15 July
Micosta Leisure Inn

Huttopia Berkshires

1.0 star property
Huttopia Berkshires

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (11)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is NZ$273
includes taxes & fees
14 July - 15 July
Taborton Harvest Boulder Pines Cabin in the woods

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

9.8 out of 10, Exceptional, (26)
"Great location "
The price is NZ$750
includes taxes & fees
10 Aug - 11 Aug
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

2 bedroom town house with game room

5.8 out of 10, (15)
"Property was easy to get to. Located right off the thruway. House was clean and located close to plenty of shopping options. There was also fast food restaurants located within walking distance. "
The price is NZ$294
includes taxes & fees
14 July - 15 July
2 bedroom town house with game room

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
The price is NZ$296
includes taxes & fees
14 July - 15 July
Taborton Harvest Timber Trails Unique cabin experience

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Private Yacht on Catskill Creek

9.6 out of 10, Exceptional, (21)
"We had a wonderful time on the boat. Melissa and AJ were wonderful hosts, very responsive. The boat tour was a highlight of a great, very relaxing weekend."
The price is NZ$407
includes taxes & fees
14 July - 15 July
Private Yacht on Catskill Creek

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

10.0 out of 10, Exceptional, (163)
"We had a fabulous time staying at the property. The game room and karaoke setup was amazing. Enjoyed cooking pizza and the outdoor kitchen. Will definitely look to book again."
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Modern Luxurious Cabin, Catskills - The Tiny Nook

10.0 out of 10, Exceptional, (5)
"The Tiny Nook is as cute and charming as the listing suggests, and came well equipped for a short getaway. It was easy to find, quiet, and felt secluded, even as the leaves were falling. The hosts were also very responsive and had some great recommendations of nearby places to visit. "
The price is NZ$705
includes taxes & fees
14 July - 15 July
Modern Luxurious Cabin, Catskills - The Tiny Nook

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.8 out of 10, Exceptional, (15)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (13)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (144)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

10.0 out of 10, Exceptional, (48)
"We had the most wonderful time! The views are unbelievable - sitting in the pool or hot tub or around the fire pit, watching the barges sail by was so special! We can’t wait to come back!"
Gorgeous Hudson River Estate-with Pool and Winter Jacuzzi

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (7)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
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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Frequently asked questions

Are there holiday rentals in Chatham?

Yes, there are holiday rentals close to the most popular sights in Chatham, or you can select a more secluded option if you're looking for a relaxing stay. Chatham is known for its theatres and restaurants.

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

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This holiday home rental outside of Chatham is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Chatham?

With 14 Expedia holiday rentals, you're guaranteed to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Kinderhook Lake. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the wider area.

What are holiday rentals like in Chatham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chatham. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll have all the comforts of home. 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 the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for families.