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

Apartments in Chatham for Rent

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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
$110 nightly
The price is $123
Nov 16 - Nov 17
Total with taxes and fees
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.
$322 nightly
The price is $361
Nov 15 - Nov 16
Total with taxes and fees
Hudson NY’S Country Serenity Guest Suite.
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

3. 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)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
$104 nightly
The price is $116
Nov 21 - Nov 22
Total with taxes and fees
Cozy 1-bedroom studio in serene Great Barrington with AC
A porch with two Adirondack chairs, a welcome mat, and a door labeled "Apartment 2".

4. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (6 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.
$197 nightly
The price is $209
Nov 15 - Nov 16
Total with taxes and fees
Berkshires Apartment at the Stephentown Hotel
A cozy living room with a large window, wooden walls, and a television.

5. 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.
$189 nightly
The price is $211
Nov 15 - Nov 16
Total with taxes and fees
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A fire pit with chairs, a ski lift, and a building with a sign that reads "Mountain Resort".

6. 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
$189 nightly
The price is $211
Nov 15 - Nov 16
Total with taxes and fees
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A bedroom with a wooden bed frame, a large window, and a painting of mountains on the wall.

7. 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, (14 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
$189 nightly
The price is $211
Nov 15 - Nov 16
Total with taxes and fees
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A snow-covered outdoor area with a fire pit, seating, and a building in the background.

8. 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.
$189 nightly
The price is $211
Nov 15 - Nov 16
Total with taxes and fees
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A room with a bed, a small table, and a chair. There is a window with blinds and a door leading to another room.

9. 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
$191 nightly
The price is $214
Nov 15 - Nov 16
Total with taxes and fees
The Brooks Motel: Exceptional Suite
A white house with a black front door, a small porch with a black railing, and a large tree in the background.

10. Sky view retreat, a serene hillside hideaway

Sky view retreat, a serene hillside hideaway
Hudson
$335 nightly
The price is $375
Nov 17 - Nov 18
Total with taxes and fees
Sky view retreat, a serene hillside hideaway
A row of multi-story buildings with a uniform architectural style, likely a hotel or resort, set against a backdrop of green hills and trees.

11. 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)
"Great place, everything was so easy!!"
United States
Dana
$189 nightly
The price is $211
Nov 15 - Nov 16
Total with taxes and fees
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

12. 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, (22 reviews)
"Great location! "
United States
shannon m.
$189 nightly
The price is $211
Nov 15 - Nov 16
Total with taxes and fees
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
A living room with a sofa, armchair, coffee table, TV, and a window with curtains.

13. 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.
$189 nightly
The price is $211
Nov 15 - Nov 16
Total with taxes and fees
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A living room with a sofa, a door, and a kitchen area in the background.

14. 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.
$157 nightly
The price is $170
Nov 16 - Nov 17
Total with taxes and fees
2 bed room Apartment
A sandy beach with a lake and forest in the background.

15. 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.
$291 nightly
The price is $325
Nov 16 - Nov 17
Total with taxes and fees
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
An outdoor seating area with Adirondack chairs and a table, surrounded by a gravel patio and a wooden fence.

16. 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.
$225 nightly
The price is $239
Nov 15 - Nov 16
Total with taxes and fees
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A gazebo and picnic tables by a lake with a clear view of the water and a bridge in the distance.

17. The Hideaway a large studio that sleeps 4 with a fireplace and tub shower

The Hideaway a large studio that sleeps 4 with a fireplace and tub shower
Catskill
9.8 out of 10, Exceptional, (8 reviews)
"Very nice place, convenient to walking to town. Would stay again if we get the chance."
United States
Gray T.
$300 nightly
The price is $336
Dec 1 - Dec 2
Total with taxes and fees
The Hideaway a large studio that sleeps 4 with a fireplace and tub shower
A wooden house with a front door, a small porch, and a garden.

18. 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.
$244 nightly
The price is $273
Nov 16 - Nov 17
Total with taxes and fees
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A lakeside beach with people swimming and sunbathing, a boat, and beach chairs.

19. Bridge Street Oasis

Bridge Street Oasis
Catskill
9.4 out of 10, Exceptional, (3 reviews)
"Bridge Street Oasis was an excellent stay!! Clean, comfortable, easy to find. Welcoming and we would definitely stay again!! Super place. "
United States
John S.
$325 nightly
The price is $364
Dec 1 - Dec 2
Total with taxes and fees
Bridge Street Oasis
A room with a bed, a small table, and a chair. There is a window with blinds and a door leading to another room.

20. 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.
$185 nightly
The price is $207
Nov 15 - Nov 16
Total with taxes and fees
The Brooks Motel: Exceptional Suite
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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"We loved the place & desk staff . Breakfast room staff was curt and dismissive."
Stephen Bond 2-night trip
Posted 3 hours ago
The Red Lion Inn

Find out more about Chatham

Chatham Apartments information

Number of reviews
198
Accommodation
111 Apartments
Lowest Price
$116
Highest Price
$375

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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