Best Apartments in Chatham, NY for Your Vacation from $132

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

Bundle & Save
Get more, spend less whenever you see Bundle & Save deals
OneKeyCash
Earn OneKeyCash on all your eligible bookings
Upfront pricing
We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chatham apartments

1. All comforts of home

Hudson

Georgine

$118 nightly

Sep 7 - Sep 8

Total with taxes and fees

2. Hudson NY’S Country Serenity Guest Suite.

Hudson

David P.

$338 nightly

Sep 7 - Sep 8

Total with taxes and fees

3. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

$170 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Great Barrington

Shelly B.

$148 nightly

Sep 13 - Sep 14

Total with taxes and fees

5. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

$246 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Hancock

Ann

$212 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Great Barrington

Kristin O.

$287 nightly

Sep 16 - Sep 17

Total with taxes and fees

8. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

$179 nightly

Sep 7 - Sep 8

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Cabins

Private vacation homes

Save an average of 15% on thousands of hotels when you're signed in

Top Chatham Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"Enjoyed our stay and would highly recommend!"

Berkshire Mountain Lodge

10/10 Excellent

"We were there for a one night stay after a show at Tanglewood. Being able to check in online in advance was excellent and saved us a lot of time. There were three of us traveling (a couple and a family member) so we requested a suite. It was huge, well appointed and so clean. The cost was incredibly reasonable for the amount of space we had! The king bed in its own bedroom was super comfortable, and the pull out couch did the job. We didn’t use any of the extra amenities, but saw a few families with children. Lots of space to roam and wander, both inside and on the property. It was an easy 15 minute drive to Tanglewood, so the location worked great for us. The only negative comment would be there was no do not disturb tag for the door, so housekeeping arrived an hour before checkout and we had to send them away. We will stay again if we are in the area, highly recommended!"

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"It’s as beautiful as described online. We love the views and all the stuff provided, even though it’s a very compact cabin setting. Every thing is good. Only one thing scared me is some ants and small insects suddenly came out from no where. Outside has mosquitoes. But if you remember it’s in a nature forest, then they should be normal. Staff are very caring and thoughtful. They provide everything we need, and even more. We are very thankful for this opportunity to be there for enjoy."

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

Find out more about Chatham

Chatham Apartments information

Number of reviews	205
Accommodation	111 Apartments
Lowest Price	$132
Highest Price	$379

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?

Listed below are some of the favorite apartments in the area to choose from: Cozy 1-bedroom studio in serene Great Barrington with AC: Located 16.7 mi/26.9 km away in Great Barrington. Free WiFi, private balconies, and Smart TVs are included. Access to onsite laundry facilities is available on site. All comforts of home: Located in Hudson, 8.8 mi/14.2 km away. Includes private balconies. Access to a hot tub 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.

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.

Explore a world of travel with Expedia

Chatham Vacation Rentals

Things to do in Albany

Apartments in Chatham for Rent

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chatham apartments

1. All comforts of home

2. Hudson NY’S Country Serenity Guest Suite.

3. The Brooks Motel: Exceptional Suite

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

5. Berkshires Apartment at the Stephentown Hotel

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

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

8. The Brooks Motel: Exceptional Suite

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

10. 2 bed room Apartment

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

12. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

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

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

15. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

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

17. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

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

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

20. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Find vacation rentals that suit your style

Top Chatham Hotel Reviews

Vacation Village in the Berkshires

Find out more about Chatham

Chatham Apartments information

Frequently asked questions

Explore a world of travel with Expedia