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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Chatham apartments

Property grounds

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is CA $190
CA $379 total
includes taxes & fees
Apr 10 - Apr 11
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Gift shop

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is CA $191
CA $380 total
includes taxes & fees
Apr 12 - Apr 13
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Property grounds

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"The condo was nice, very convenient. The outdoor pool and hot tub were closed. Not the owners fault but a bummer for my kids. "
United States
Candice M.
The price is CA $190
CA $379 total
includes taxes & fees
Apr 10 - Apr 11
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Indoor pool

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is CA $191
CA $380 total
includes taxes & fees
Apr 12 - Apr 13
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
1 bedroom, WiFi, bed sheets

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (12 reviews)
"Room was perfect location for skiing. Able to see slopes and a few of the chairlifts from room. Beds were super comfortable. Parking was close by and in private area which helped avoid parking in huge resort parking lot. Owner was very responsive."
United States
Charles
The price is CA $190
CA $379 total
includes taxes & fees
Apr 10 - Apr 11
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is CA $190
CA $379 total
includes taxes & fees
Apr 10 - Apr 11
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Indoor pool

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.8 out of 10, Exceptional, (21 reviews)
"Great location! "
United States
shannon m.
The price is CA $190
CA $379 total
includes taxes & fees
Apr 10 - Apr 11
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is CA $207
CA $263 total
includes taxes & fees
Apr 26 - Apr 27
The Brooks Motel: Exceptional Suite
Pool

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Quiet location"
United States
Alicia S.
The price is CA $191
CA $380 total
includes taxes & fees
Apr 12 - Apr 13
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Pool

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (34 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is CA $271
CA $520 total
includes taxes & fees
Apr 12 - Apr 13
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Beach

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is CA $174
CA $353 total
includes taxes & fees
Apr 12 - Apr 13
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Indoor pool, a heated pool

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is CA $191
CA $380 total
includes taxes & fees
Apr 12 - Apr 13
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Outdoor dining

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (7 reviews)
"Great room decorations, travel with two kids they have a great time playing video games"
United States
Andres
The price is CA $191
CA $380 total
includes taxes & fees
Apr 12 - Apr 13
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Pool

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
United States
Maura S.
The price is CA $190
CA $379 total
includes taxes & fees
Apr 10 - Apr 11
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Exterior

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
The price is CA $189
CA $378 total
includes taxes & fees
Apr 10 - Apr 11
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Pool

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is CA $191
CA $380 total
includes taxes & fees
Apr 12 - Apr 13
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
TV, offices

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
9.2 out of 10, Wonderful, (5 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is CA $218
CA $277 total
includes taxes & fees
Apr 17 - Apr 18
The Brooks Motel: Exceptional Suite
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is CA $136
CA $183 total
includes taxes & fees
Apr 12 - Apr 13
All comforts of home
1 bedroom, iron/ironing board, WiFi, bed sheets

Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere

Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Thank you for being a great host. "
United States
Rony N.
The price is CA $184
CA $370 total
includes taxes & fees
Apr 16 - Apr 17
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- The Most Magical Berkshire Retreat Anywhere
A heated pool

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Hancock
9.6 out of 10, Exceptional, (5 reviews)
"My family loved our stay here at Jiminy! You can’t beat the ski in and ski out feature, in addition to dining and several amenities all within the resort. Howard was an attentive and communicative host, ensuring we had everything our needed to have the best stay possible. We will definitely be returning!"
United States
katie s.
The price is CA $191
CA $380 total
includes taxes & fees
Apr 12 - Apr 13
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
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

Hotel On North

Hotel On North

10/10 Excellent
"Charming hotel in the middle of Pittsfield. Love the art, decor and overall fell. Rooms are charming and cozy. Staff is friendly and welcoming. Great spot to stay with the kids (playroom downstairs is awesome). Love the touch of complementary coffee/tea/hot chocolate - always beautifully stocked and well maintained with great selection of products."
Karina 2-night trip
Posted 12 hours ago
Hotel On North

Find out more about Chatham

Chatham Apartments information

Number of reviews
254
Accommodation
110 Apartments
Lowest Price
CA $183
Highest Price
CA $520

Frequently asked questions

What's it like to stay at an apartment in Chatham?
There are plenty of places to stay in Chatham with 26 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: 3 Bedroom Hudson Valley Loft with private porch in the heart of Chatham Village: Situated in Chatham, 0.3 mi/0.5 km from the heart of Chatham. Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located 16.7 mi/26.9 km away in Great Barrington. Free WiFi, separate dining areas, and Smart TVs are included. Access to onsite laundry facilities is available on site. All comforts of home: Located 8.8 mi/14.2 km away in Hudson. Amenities include private balconies. Access to a hot tub is available on site. 2 bed room Apartment: It's located in Albany, 20.7 mi/33.4 km from Chatham. Includes free WiFi, private patios, and separate dining areas.
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 Hudson Chatham Winery 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.

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