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Compare 98 Apartments in Chatham with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.2 out of 10, Wonderful, (12)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

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."
The price is SAR 589
SAR 1,101 total
includes taxes & fees
2 Feb - 3 Feb
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

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

10.0 out of 10, Exceptional, (5)
"Condo was conveniently located at the base of the mountain. Had everything you would need for a quick weekend getaway. Owner was available for any questions."
The price is SAR 589
SAR 1,101 total
includes taxes & fees
5 Feb - 6 Feb
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

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

10.0 out of 10, Exceptional, (4)
"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "
The price is SAR 589
SAR 1,101 total
includes taxes & fees
3 Feb - 4 Feb
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect location. Walking distance. Brand new apartment. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

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

9.6 out of 10, Exceptional, (30)
"Perfect 1 bedroom, ski in ski off , updated unit with great amenities! Owner super responsive and accommodating. Will definitely be back "
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (7)
"This is the second year we had our girls weekend at the Penthouse and it did not disappoint. The place is updated, very clean, and in a great location! Only suggestion would to get a nice big sectional couch! We had 8 people and not enough comfy seating. But beautiful apartment!! "
The Penthouse, Downtown Lenox by Evergreen Home

Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

2.0 star property
9.0 out of 10, Wonderful, (2)
"Our stay was excellent overall! We really admired the tidiness of the property. The ski trails were hit to. The only thing that brought this review down was that the T.V.’s in our room were not working but the stay was pretty good!"
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (23)
"Everything was great. Very clean unit and it def is a ski in/out. Plenty of space in bedrooms. Howard is easy to communicate with and a great host. Truly a gem in jimminy peak. "
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

All comforts of home

9.8 out of 10, Exceptional, (36)
"Quaint and comfortable"
The price is SAR 409
SAR 517 total
includes taxes & fees
3 Mar - 4 Mar
All comforts of home

Restored 19th century farmhouse apartment 2 -charming farmland and town culture!

9.4 out of 10, Exceptional, (12)
"We had a great trip to this lovely home! Clean and cute, near beautiful nature and easy access to grocery stores."
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!

Modern Copake Falls Getaway

9.8 out of 10, Exceptional, (28)
"Unbeatable accommodations, especially for the price. Would stay again, gorgeous sunrise and sunset, very peaceful. Wish I could live there part time!"
Modern Copake Falls Getaway

Hip on Warren

10.0 out of 10, Exceptional, (9)
"Apartment is adorable and right on Warren that has everything you could want for a quick visit to upstate NY. Restaurants , stores of all kinds and great coffee shops and bars. "
The price is SAR 1,031
SAR 1,500 total
includes taxes & fees
3 Feb - 4 Feb
Hip on Warren

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

9.8 out of 10, Exceptional, (17)
"The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again."
The price is SAR 589
SAR 1,101 total
includes taxes & fees
2 Feb - 3 Feb
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

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

10.0 out of 10, Exceptional, (2)
"Stayed one night at one of my favorite ski spots. Will be back again!"
The price is SAR 589
SAR 1,101 total
includes taxes & fees
2 Feb - 3 Feb
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Baldwin Hill Retreat Guest House

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property and neighborhood were gorgeous! Walkable roads with low speed limits and a nearby park were major bonuses. Plenty of food options nearby, and downtown Great Barrington is only a short drive away. The house was super clean, gorgeously furnished, and very cozy. The beds and linens were very good quality and I had an incredibly restful stay. I will certainly be renting this spot for my next trip to the area! "
Baldwin Hill Retreat Guest House

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (22)
"We’ve always had a great experience with Downtown Upstairs in Lenox and this was no exception. Easy access to the downtown stores and restaurants with the comfort of a nice, clean, well furnished apartment. "
Renovated Downtown 1bedroom

2 bed room Apartment

The price is SAR 450
SAR 724 total
includes taxes & fees
1 Feb - 2 Feb
2 bed room Apartment

Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

9.6 out of 10, Exceptional, (23)
"We were treated with such kindness and understanding of our situation. We would gladly recommend Alisha to anyone wanting to stay at their property. In fact, we are going back in May. "
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
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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Other property types in Chatham

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1759)
"Great place "
The price is SAR 563
SAR 655 total
includes taxes & fees
3 Feb - 4 Feb
Vacation Village in the Berkshires

Postcard Cabins Eastern Catskills

2.0 star property
7.4 out of 10, Good, (3)
"This tiny cabin was a dream. It has everything you need for a cozy, nature getaway. "
The price is SAR 375
SAR 405 total
includes taxes & fees
5 Feb - 6 Feb
Postcard Cabins Eastern Catskills

The Ponds at Foxhollow by Capital Vacations

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is SAR 867
SAR 969 total
includes taxes & fees
14 Feb - 15 Feb
The Ponds at Foxhollow by Capital Vacations
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.

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: 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor: Located in Hancock, 20.4 mi/32.8 km from the heart of Chatham. Includes sofa beds. A fitness center and an indoor pool are on site. 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. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor: Located in Hancock, 20.4 mi/32.8 km away. Includes sofa beds. A fitness center and a spa tub are on site. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone: Located 20.4 mi/32.8 km away in Hancock. Amenities include sofa beds. A fitness center and an indoor pool are on site. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: It’s located in Lee, 18 mi/29 km from Chatham. Includes private patios and fireplaces.
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.