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Compare 93 Apartments in Chatham with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
9.6 out of 10, Exceptional, (8)
"Super cute, cozy and excellent location. Loved our stay. Will be back!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Charming Apartment In Berkshire Victorian Home
7.8 out of 10, Good, (7)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.8 out of 10, Exceptional, (20)
"the owner was very nice and helpfull"
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
The Brooks Motel: Exceptional Suite
10.0 out of 10, Exceptional, (2)
"The motel was well equipped, clean, and comfortable. It was especially suited for my travel with my dog."
The price is AED 584
AED 708 total
includes taxes & fees
15 Nov - 16 Nov
The Brooks Motel: Exceptional Suite
Garfield House Studio at 208
9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
Garfield House Studio at 208
Hip on Warren
10.0 out of 10, Exceptional, (7)
"This was the absolute best location we ever could have hoped for. We had an easy walk to every place that we wanted to go and on top of that, the apartment is spotless and obviously very well taken care of. Very nice and comfortable space. The host is great to deal with. We would definitely stay here again."
The price is AED 1,010
AED 1,462 total
includes taxes & fees
17 Nov - 18 Nov
Hip on Warren
Private apartment in beautiful country barn
10.0 out of 10, Exceptional, (18)
"Great farmhouse in the Berkshires. Location is out of the way without being out of the way. Communications with the host is great. Very accommodating."
Private apartment in beautiful country barn
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
9.4 out of 10, Exceptional, (11)
"Cute, quite apartment on the second floor. Enjoyed coffee on the small deck looking out at the farm animals on a cool, crisp and sunny fall morning. Perfect place as base camp for our weekend adventures in the area!"
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Lake house with wrap around porch&beautiful view, minutes from the NYS Capitol!
8.6 out of 10, Excellent, (8)
"Beautiful location and comfortable and clean. Would highly recommend. "
Lake house with wrap around porch&beautiful view, minutes from the NYS Capitol!
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
9.2 out of 10, Wonderful, (9)
"Such a awesome facility! Love the room, the Jiminy property is very cool and you don’t even need to leave to go anywhere else because there is so much to do here. Stay."
The price is AED 382
AED 828 total
includes taxes & fees
17 Nov - 18 Nov
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Main Street Delight 1bedroom
10.0 out of 10, Exceptional, (18)
"The location was fantastic for our stay in the Berkshires. Walkable to many restaurants & shops. It was very well decorated & cozy. Very convenient being above a coffee shop, however not ideal if you enjoy sleeping in. We could hear the consistent squeaking of the coffee shop door as soon as it opened in the morning (~7:00 am) from the bedroom. However, good motivation to get up and enjoy the beautiful Berkshires!"
Main Street Delight 1bedroom
Heart of Lenox!! - renovated downtown apartment
10.0 out of 10, Exceptional, (63)
"The bathroom was less than tidy and when I recall it was like that last time. Bathroom rug is dirty or just dirty looking. I advise property Meg to buy several Along with a Terry bath mat so you can cover it when using. No little extras like soap/shampoo are offered. I had My own. Overall the apartment is very cute would stay again. "
Heart of Lenox!! - renovated downtown apartment
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
9.6 out of 10, Exceptional, (29)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
The price is AED 382
AED 828 total
includes taxes & fees
17 Nov - 18 Nov
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
9.6 out of 10, Exceptional, (21)
"Nice little cabin on a beautiful piece of property. The dirt road leading to the house was very narrow and bumpy but looks like they were in the process of smoothing out the road. The cabin is very cute inside and clean. We had three people so inside there’s not a lot of seating but it’s a tiny house so there’s not a lot of space for them to add additional seating. Just something to keep in mind. They do allow dogs. Our dog really enjoyed swimming in the pond. Wish they’d had a hose to bath her...
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
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 AED 382
AED 828 total
includes taxes & fees
17 Nov - 18 Nov
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
2 bed room Apartment
The price is AED 441
AED 716 total
includes taxes & fees
16 Nov - 17 Nov
2 bed room Apartment
Gateway to the Berkshires - Renovated downtown apartment
10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
Downtown Hudson Apartment: Walk to Cafes & River!
10.0 out of 10, Exceptional, (1)
"A great find in Hudson, NY. Location was perfect for exploring downtown. Host was helpful when we needed something. Washer & dryer were nice amenities to have while traveling. Definitely would recommend for anyone staying in the area! "
Downtown Hudson Apartment: Walk to Cafes & River!
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
2.0 star property
10.0 out of 10, Exceptional, (1)
"This location was perfect for hiking the AT. The trail is only a few feet from the front door. The backyard is very nice, and they had chairs and tables to sit out. The apartment was a nice size for two people. There was no tv, so we used our computer. The kitchen was great to have since we didn't plan on eating out every night. There are plenty of restaurants in the area. The hosts were great and very responsive. The fall colors made the trip extra special."
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
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, (1746)
"Love staying here "
The price is AED 620
AED 717 total
includes taxes & fees
16 Nov - 17 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (919)
"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "
The price is AED 542
AED 594 total
includes taxes & fees
17 Nov - 18 Nov
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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: Hip on Warren: Situated in Hudson, 12.6 mi/20.2 km from the heart of Chatham. Includes free WiFi and Smart TVs. New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.: Located 12.8 mi/20.6 km away in Richmond. 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 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.