A city street with buildings, parked cars, and solar panels.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Chatham apartments

A wooden deck with a staircase leading to a covered porch area.

1. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (63 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
The price is CA $140
CA $188 total
includes taxes & fees
Oct 20 - Oct 21
All comforts of home
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

2. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.2 out of 10, Wonderful, (5 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is CA $283
CA $545 total
includes taxes & fees
Oct 12 - Oct 13
Hudson NY’S Country Serenity Guest Suite.
A closet with a red bag hanging on the left and several black hangers on a rod.

3. Sky view retreat, a serene hillside hideaway

Sky view retreat, a serene hillside hideaway
Hudson
The price is CA $235
CA $478 total
includes taxes & fees
Oct 31 - Nov 1
Sky view retreat, a serene hillside hideaway
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

4. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
The price is CA $213
CA $271 total
includes taxes & fees
Oct 11 - Oct 12
The Brooks Motel: Exceptional Suite
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

5. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.6 out of 10, Excellent, (7 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is CA $128
CA $199 total
includes taxes & fees
Oct 18 - Oct 19
Cozy 1-bedroom studio in serene Great Barrington with AC
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

6. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is CA $125
CA $321 total
includes taxes & fees
Oct 12 - Oct 13
Berkshires Apartment at the Stephentown Hotel
A snow-covered outdoor area with a fire pit, tables, and chairs.

7. 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)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is CA $189
CA $381 total
includes taxes & fees
Oct 14 - Oct 15
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A sandy beach with a lake and forest in the background.

8. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (6 reviews)
The price is CA $297
CA $464 total
includes taxes & fees
Oct 12 - Oct 13
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

9. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is CA $189
CA $381 total
includes taxes & fees
Oct 14 - Oct 15
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

10. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (8 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 $225
CA $284 total
includes taxes & fees
Oct 12 - Oct 13
The Brooks Motel: Exceptional Suite
A living room with a sofa, a door, and a kitchen area in the background.

11. 2 bed room Apartment

2 bed room Apartment
South End
8.4 out of 10, Very good, (12 reviews)
"Great communication and lovely place "
United States
Jude M.
The price is CA $135
CA $255 total
includes taxes & fees
Oct 13 - Oct 14
2 bed room Apartment
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

12. 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, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is CA $189
CA $381 total
includes taxes & fees
Oct 14 - Oct 15
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

13. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

14. 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)
The price is CA $164
CA $387 total
includes taxes & fees
Oct 12 - Oct 13
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A sign for The Stephentown Hotel with a depiction of a red building and mountains.

15. 2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (7 reviews)
"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 CA $188
CA $425 total
includes taxes & fees
Oct 12 - Oct 13
2 Bed Berkshire Getaway @ Stephentown Hotel
A covered outdoor seating area with two chairs and a view of a grassy landscape.

16. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
The price is CA $320
CA $453 total
includes taxes & fees
Oct 11 - Oct 12
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

17. 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)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is CA $189
CA $381 total
includes taxes & fees
Oct 14 - Oct 15
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

18. 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)
The price is CA $189
CA $381 total
includes taxes & fees
Oct 14 - Oct 15
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

19. Urban Peak Escape, Lenox, MA

Urban Peak Escape, Lenox, MA
Lenox
8.0 out of 10, Very good, (1 review)
"Very nice. A few suggestions:- A higher end coffee maker would go a long way, or a latte machine. - Needs a toaster- Instructions on how to work the shower. We could only get the primary shower to work- A table and chairs (for eating a meal) would be good. Otherwise very comfortable and clean, and great location! "
United States
Nancy H.
The price is CA $600
CA $1,084 total
includes taxes & fees
Oct 14 - Oct 15
Urban Peak Escape, Lenox, MA
A living room with a sofa, armchairs, a TV, a fireplace, and a large window.

20. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is CA $243
CA $488 total
includes taxes & fees
Nov 3 - Nov 4
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
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

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

10/10 Excellent
"Beautiful building. Glad to see it repurposed."
Vivien 1-night trip
Posted 1 hour ago
Pocketbook Hotel and Bath

Find out more about Chatham

Chatham Apartments information

Number of reviews
201
Accommodation
111 Apartments
Lowest Price
CA $188
Highest Price
CA $1,084

Frequently asked questions

What's it like to stay at an apartment in Chatham?
You'll find 5 apartments to choose from in Chatham for your trip.
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: Cozy 1-bedroom studio in serene Great Barrington with AC: Located in Great Barrington, 16.7 mi/26.9 km from the heart of Chatham. Includes free WiFi, private balconies, and Smart TVs. Access to onsite laundry facilities is available on site. Cozy 1-bedroom apartment in old farm house in historic South Lee: Located 17.4 mi/28.1 km away in South Lee. Amenities include private patios. Access to onsite laundry facilities is available on site. Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located in Great Barrington, 16.7 mi/26.9 km away. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site.
How many apartments will I find in Chatham?
Expedia has 5 apartments to book in Chatham.
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 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'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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