Chatham Vacation Rentals

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Check prices for these dates

Tonight
Aug 18 - Aug 19
Tomorrow
Aug 19 - Aug 20
This weekend
Aug 22 - Aug 24
Next weekend
Aug 29 - Aug 31

Vacation Rentals in Chatham

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1954)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is ￥15,943
￥19,424 total
includes taxes & fees
Aug 27 - Aug 28
Vacation Village in the Berkshires
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.6 out of 10, Exceptional, (58)
"Really beautiful place to enjoy nature with family!!"
The price is ￥24,875
￥32,429 total
includes taxes & fees
Aug 20 - Aug 21
Postcard Cabins Eastern Catskills
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (962)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is ￥23,403
￥26,141 total
includes taxes & fees
Sep 1 - Sep 2
Jiminy Peak Mountain Resort
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (115)
"Great stay!"
The price is ￥19,126
￥21,422 total
includes taxes & fees
Aug 20 - Aug 21
Micosta Leisure Inn
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect place for a relaxing getaway! We loved everything! "
The price is ￥14,425
￥16,113 total
includes taxes & fees
Sep 1 - Sep 2
Huttopia Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (125)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow
Taborton Harvest Boulder Pines Cabin in the woods
Exterior detail

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 ￥19,135
￥27,938 total
includes taxes & fees
Aug 19 - Aug 20
Taborton Harvest Boulder Pines Cabin in the woods
Spacious 5-bedroom house in charming Lee with WiFi
5 bedrooms, iron/ironing board, WiFi, bed sheets

Spacious 5-bedroom house in charming Lee with WiFi

The price is ￥62,556
￥117,390 total
includes taxes & fees
Aug 25 - Aug 26
Spacious 5-bedroom house in charming Lee with WiFi
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Exterior

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

9.8 out of 10, Exceptional, (27)
"Great location "
The price is ￥24,507
￥51,425 total
includes taxes & fees
Aug 25 - Aug 26
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
Taborton Harvest Timber Trails Unique cabin experience
Fridge, microwave, oven, stovetop

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 ￥19,135
￥27,775 total
includes taxes & fees
Aug 19 - Aug 20
Taborton Harvest Timber Trails Unique cabin experience
Private Yacht on Catskill Creek
Property grounds

Private Yacht on Catskill Creek

9.6 out of 10, Exceptional, (25)
"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 ￥21,858
￥36,165 total
includes taxes & fees
Aug 19 - Aug 20
Private Yacht on Catskill Creek
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

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
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is ￥80,660
￥154,002 total
includes taxes & fees
Aug 20 - Aug 21
Hancock Village Inn at Jiminy Peak
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach
Terrace/patio

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

10.0 out of 10, Exceptional, (166)
"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
Heaven Can't Wait, On Beautiful Kinderhook Lake!!
Property grounds

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

9.8 out of 10, Exceptional, (85)
"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!!
The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

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
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is ￥23,698
￥71,667 total
includes taxes & fees
Aug 20 - Aug 21
Comfortable Berkshires retreat on mtn resort, SISO
Rose Cottage
Outdoor dining

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage
Modern Luxurious Cabin, Catskills - The Tiny Nook
Exterior

Modern Luxurious Cabin, Catskills - The Tiny Nook

10.0 out of 10, Exceptional, (5)
"The place was clean and just like the pictures. The hosts we great and communication was great. Definitely will stay here again. Already recommended it to a few friends!"
The price is ￥23,550
￥48,961 total
includes taxes & fees
Sep 15 - Sep 16
Modern Luxurious Cabin, Catskills - The Tiny Nook
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Outdoor banquet area

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

9.6 out of 10, Exceptional, (88)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
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

St. Charles Hotel

St. Charles Hotel

10/10 Excellent
"Zach at the front desk was so accommodating. If he goes, that place is going under."
Kathy 4-night trip
Posted 6 hours ago
St. Charles Hotel

Frequently asked questions

Are there vacation rentals in Chatham?

Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

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

Deluxe Queen Room with 2 Queen Beds: This vacation home rental near Chatham is equipped with an outdoor pool, air-conditioning, and WiFi to help you feel comfortable during your stay.

How many vacation rentals are there in Chatham?

With 13 Expedia vacation rentals, you're sure 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 larger area.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.