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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Chatham apartments

Pool
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
10.0 out of 10, Exceptional, (1)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Beach
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is AED 491
AED 914 total
includes taxes & fees
11 Jan - 12 Jan
Berkshires Apartment at the Stephentown Hotel
Property grounds
All comforts of home

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is AED 360
AED 486 total
includes taxes & fees
10 Jan - 11 Jan
All comforts of home
Gift shop
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Apartment in Hancock

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment in Hancock

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Property grounds
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Apartment in Hancock

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (5)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Desk, iron/ironing board, WiFi, bed sheets
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is AED 584
AED 736 total
includes taxes & fees
11 Jan - 12 Jan
The Brooks Motel: Exceptional Suite
Pool
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Apartment in Hancock

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
9.4 out of 10, Exceptional, (16)
"Nice Place"
United States
Tom C.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Pool
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Apartment in Hancock

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Private kitchen
Lenox Half Duplex

Apartment in Lee

Lenox Half Duplex
2.0 star property
The price is AED 555
AED 1,379 total
includes taxes & fees
10 Jan - 11 Jan
Lenox Half Duplex
Smart TV
2 bed room Apartment

Apartment in South End

2 bed room Apartment
8.8 out of 10, Excellent, (8)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
The price is AED 349
AED 655 total
includes taxes & fees
12 Jan - 13 Jan
2 bed room Apartment
Pool
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Apartment in Hancock

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.8 out of 10, Exceptional, (31)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is AED 775
AED 1,440 total
includes taxes & fees
15 Jan - 16 Jan
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Property grounds
2 Bed Berkshire Getaway @ Stephentown Hotel

Apartment in Stephentown

2 Bed Berkshire Getaway @ Stephentown Hotel
10.0 out of 10, Exceptional, (5)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
The price is AED 648
AED 1,176 total
includes taxes & fees
11 Jan - 12 Jan
2 Bed Berkshire Getaway @ Stephentown Hotel
Indoor pool, a heated pool
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Apartment in Hancock

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
9.4 out of 10, Exceptional, (6)
"Great location. Very nice vacation. Would def go again. "
United States
Elizabeth M.
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Beach
2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Apartment in Stephentown

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
8.4 out of 10, Very Good, (12)
"Great location and property. thank you"
United States
Christine P.
The price is AED 559
AED 1,017 total
includes taxes & fees
11 Jan - 12 Jan
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Exterior
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Apartment in Hancock

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
10.0 out of 10, Exceptional, (1)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
United States
Antonio S.
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Outdoor dining
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Apartment in Hancock

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
10.0 out of 10, Exceptional, (3)
"Great room decorations, travel with two kids they have a great time playing video games"
United States
Andres
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Indoor pool
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Apartment in Hancock

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
9.8 out of 10, Exceptional, (20)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Property grounds
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Apartment in Hancock

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
9.2 out of 10, Wonderful, (12)
"We enjoyed our stay. We would definitely stay here again in the future."
United States
Scott
The price is AED 503
AED 1,013 total
includes taxes & fees
13 Jan - 14 Jan
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
1 bedroom, iron/ironing board, WiFi, bed sheets
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere

Apartment in Hancock

Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere
10.0 out of 10, Exceptional, (1)
"Great!"
United States
Susan M.
The price is AED 503
AED 1,013 total
includes taxes & fees
11 Jan - 12 Jan
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere
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

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"I loved every single part of the stay "
Srijana 1-night trip
Posted 11 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Frequently asked questions

What's it like to stay at an apartment in Chatham?
There are plenty of places to stay in Chatham with 25 hotels and other accommodations. Though there aren't many apartments, we can help you find similar accommodations. When you search for a place to stay on Expedia, you can filter by amenities you might find in an apartment such as a kitchen. Even filter by similar properties such as condos, vacation homes, or cottages.
Why would you choose apartments instead of traditional hotels?
An apartment comes equipped with a kitchen, so you can cook some of your meals, and usually is more spacious than a traditional hotel room. Apartments are a good option for couples looking to stay away from the tourist areas, but also for families who want the conveniences of home.
What's the top apartment I should consider for a stay in Chatham?
Below are some of the favorite apartments in the area: Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located in Great Barrington, 16.7 mi/26.9 km from the heart of Chatham. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn: Located 20.4 mi/32.8 km away in Hancock. Amenities include sofa beds. A fitness center and onsite laundry facilities are on site. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 18 mi/29 km away. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous: Located 20.5 mi/32.9 km away in Hancock. Fireplaces and sofa beds are included. A fitness center and onsite laundry facilities are on site. All comforts of home: Located in Hudson, 8.8 mi/14.2 km from Chatham. Includes private balconies. Access to a hot tub is available on site.
What will the weather be like in Chatham?
Weather is only one factor, but it can really affect your travel plans, especially if you're planning an extended stay in Chatham. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Chatham are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What should 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 larger area.
What's the best way to get to and around Chatham?
Knowing a bit about the transportation options can make your trip smoother when you get to your destination. Fly into Hudson, NY (HCC-Columbia County), which is located 7.7 mi (12.4 km) from the city center. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 16 mi (25.8 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.