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, (1923)
"Great stay with all plenty of things to do…"
The price is AU$167
includes taxes & fees
25 Aug - 26 Aug
Vacation Village in the Berkshires

Postcard Cabins Eastern Catskills

2.0 star property
9.4 out of 10, Exceptional, (47)
"Nice stays 👌 "
The price is AU$340
includes taxes & fees
3 Aug - 4 Aug
Postcard Cabins Eastern Catskills

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (957)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is AU$274
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (110)
"As usual great place "
The price is AU$217
includes taxes & fees
11 Aug - 12 Aug
Micosta Leisure Inn

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (124)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

Huttopia Berkshires

1.0 star property
The price is AU$169
includes taxes & fees
1 Sept - 2 Sept
Huttopia Berkshires

Spacious 5-bedroom house in charming Lee with WiFi

The price is AU$1,296
includes taxes & fees
11 Aug - 12 Aug
Spacious 5-bedroom house in charming Lee with WiFi

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

9.8 out of 10, Exceptional, (83)
"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"
Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is AU$257
includes taxes & fees
3 Aug - 4 Aug
Taborton Harvest Boulder Pines Cabin in the woods

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage

2 bedroom town house with game room

5.8 out of 10, (16)
"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. "
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 AU$277
includes taxes & fees
3 Aug - 4 Aug
Taborton Harvest Timber Trails Unique cabin experience

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is AU$1,635
includes taxes & fees
4 Aug - 5 Aug
Hancock Village Inn at Jiminy Peak

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

9.8 out of 10, Exceptional, (27)
"Great location "
The price is AU$551
includes taxes & fees
19 Aug - 20 Aug
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Private Yacht on Catskill Creek

9.6 out of 10, Exceptional, (22)
"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 AU$384
includes taxes & fees
5 Aug - 6 Aug
Private Yacht on Catskill Creek

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (2)
"The chemical smell in the room was overwhelming. There was no personal contact We called the number provided and was told We would get a full refund."
The price is AU$208
includes taxes & fees
1 Sept - 2 Sept
Deluxe Queen Room with 2 Queen Beds

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

9.8 out of 10, Exceptional, (146)
"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

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

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

9.6 out of 10, Exceptional, (88)
"Our group had a great time. The place is a bit dated but has room for plenty of people."
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

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

10.0 out of 10, Exceptional, (164)
"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
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 Chatham Hotel Reviews

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?

Spacious 5-bedroom house in charming Lee with WiFi: This holiday home rental outside of Chatham offers a fireplace, a BBQ and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a dishwasher and a microwave can make your holiday run smoothly.

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 Art Omi International Arts Center - Fields Sculpture Park. 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.