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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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, (65 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 €123
includes taxes & fees
1 Nov - 2 Nov
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
9.4 out of 10, Exceptional, (6 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is €347
includes taxes & fees
1 Nov - 2 Nov
Hudson NY’S Country Serenity Guest Suite.
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

3. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is €176
includes taxes & fees
30 Oct - 31 Oct
The Brooks Motel: Exceptional Suite
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (10 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 €116
includes taxes & fees
6 Nov - 7 Nov
Cozy 1-bedroom studio in serene Great Barrington with AC
A cozy room with a bed, a wooden dresser, a coffee bar, and a dining area.

5. Sky view retreat, a serene hillside hideaway

Sky view retreat, a serene hillside hideaway
Hudson
The price is €370
includes taxes & fees
29 Nov - 30 Nov
Sky view retreat, a serene hillside hideaway
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

6. 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 €213
includes taxes & fees
1 Nov - 2 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

7. 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, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
United States
David
The price is €213
includes taxes & fees
1 Nov - 2 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A Country Inn with a large, welcoming entrance and a parking area.

8. 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 €218
includes taxes & fees
2 Nov - 3 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A sign for The Stephentown Hotel with a logo featuring a building and mountains.

9. 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.
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A lobby with leather sofas, a fireplace, and a stone wall.

10. 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 €213
includes taxes & fees
1 Nov - 2 Nov
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

11. 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 €213
includes taxes & fees
1 Nov - 2 Nov
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

12. 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)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is €213
includes taxes & fees
1 Nov - 2 Nov
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A residential garden with a stone border, various plants, and a house in the background.

13. 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, (7 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is €311
includes taxes & fees
2 Nov - 3 Nov
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

14. 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 €208
includes taxes & fees
30 Oct - 31 Oct
The Brooks Motel: Exceptional Suite
A living room with a sofa, a door, and a kitchen area in the background.

15. 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 €164
includes taxes & fees
11 Nov - 12 Nov
2 bed room Apartment
A wooden deck with outdoor furniture, a glass door leading to a view of a grassy area with trees.

16. 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 €284
includes taxes & fees
3 Nov - 4 Nov
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

17. 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 €230
includes taxes & fees
1 Nov - 2 Nov
Berkshires Apartment at the Stephentown Hotel
A modern kitchen with a dining area, built-in shelves, and a large window.

18. 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 €278
includes taxes & fees
30 Oct - 31 Oct
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.

19. 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, (35 reviews)
"We really enjoyed our stay it was a very nice place for a family."
United States
Shmaya G.
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

20. 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 €218
includes taxes & fees
1 Nov - 2 Nov
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
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
"Great"
Oneal 2-night trip
Posted 8 hours ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Find out more about Chatham

Chatham Apartments information

Number of reviews
222
Accommodation
110 Apartments
Lowest Price
€116
Highest Price
€370

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 stay.
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 often has more space than a traditional hotel room. Apartments are a good option for solo travellers who want to live like locals, but also for families who want the conveniences of home.
What's the top apartment I should consider for a stay in Chatham?
Here are some of the favourite 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, a balcony and a Smart TV . Access to on-site 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 a patio . Access to on-site 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, a dining area and a Smart TV . Access to on-site laundry facilities is available on site .
How many apartments will I be able to find in Chatham?
Expedia has 5 apartments to book in Chatham.
What will the weather be like when I travel to 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 temperature of 20°C, while the coldest months are January and February, with an average of -2°C. The snowiest months in Chatham are January, March, February and November, with each month seeing an average of 18 cm 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 wider area.
What's the best way to get to and around Chatham?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Hudson, NY (HCC-Columbia County), which is located 7.7 mi (12.4 km) away from the heart of the city. Otherwise, you can search for flights to Pittsfield, MA (PSF-Pittsfield Municipal), which is 16 mi (25.8 km) away. If you'd like to venture out around the area, consider renting a car to explore more sights.