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Compare 92 Apartments in Chatham with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Interior
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
9.4 out of 10, Exceptional, (3)
"Spacious roomy 2 bedroom in an amazing location walkable to downtown Great Barrington. Roomy kitchen. Highly recommended "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Private apartment in beautiful country barn
Living area
Private apartment in beautiful country barn
10.0 out of 10, Exceptional, (14)
"We had a beautiful visit to Massachusetts thanks to this lovely spot. The apartment was perfect, beautifully decorated, very comfortable, located in a lovely area and close to key spots we were visiting. Our host could not have been more helpful. She was very helpful leading up to our stay and throughout our time there. We could not have asked for a better experience!"
Private apartment in beautiful country barn
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Beautiful State of Art Kitchen Awaits in this spacious 900 Sq FT Suite
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.8 out of 10, Exceptional, (19)
"the owner was very nice and helpfull"
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Gateway to the Berkshires - Renovated downtown apartment
Room
Gateway to the Berkshires - Renovated downtown apartment
10.0 out of 10, Exceptional, (6)
"Emmy is a great hostess. The apartment is nicely appointed and in a great location to restaurants and shops and attractions in the Berkshires. "
Gateway to the Berkshires - Renovated downtown apartment
Garfield House Studio at 208
Exterior
Garfield House Studio at 208
9.8 out of 10, Exceptional, (24)
"A great location for a number of cultural experiences in the Berkshires, and walking distance to the shops and restaurants of the town of Lee. The studio is small, but the murphy bed is incredibly comfortable so it has all the benefits of a hotel room, with the addition of a kitchen and a porch from which to watch the world of Lee go by."
Garfield House Studio at 208
Apartment In Historic 1785 Thomas Jenkins House
Living area
Apartment In Historic 1785 Thomas Jenkins House
10.0 out of 10, Exceptional, (68)
"We were looking for a rental near a wedding in Catskill and found this lovely apartment. The proprietor was very responsive and accessing the unit was easy and no-fuss. All the details inside are lovingly selected and the unit is very well-maintained. The towels were fluffy and the sheets were soft -- we slept so well! Hudson itself and the surrounding area is SO charming. We found several delightful things to do at and in between wedding events, including dining at Feast & Floret (downtown...
Apartment In Historic 1785 Thomas Jenkins House
51 Church Street, Lenox MA - One Bedroom Unit
Living area
51 Church Street, Lenox MA - One Bedroom Unit
10.0 out of 10, Exceptional, (19)
"Fine"
51 Church Street, Lenox MA - One Bedroom Unit
Loft near Hancock Shaker Village, Birch
Dining
Loft near Hancock Shaker Village, Birch
6.0 out of 10, (2)
"No sheets for roll away bed Filthy dirty windows No way to make coffee Keurig was promised we had to borrow one from the family in the area we were visiting. Musty smell Peeling chipping paint on deck stairs and railings Dirty deck and rotten boards on deck Was clean on the inside. Dirty air conditioners in windows Other renters work trucks parked directly in from of the stairs we needed to use to enter the loft apartment Trash on the ground "
The price is SAR 428
SAR 762 total
includes taxes & fees
25 Sep - 26 Sep
Loft near Hancock Shaker Village, Birch
Restored 19th century farmhouse apartment 1- charming farmland and town culture!
Dining
Restored 19th century farmhouse apartment 1- charming farmland and town culture!
9.6 out of 10, Exceptional, (11)
"Property was clean, quiet, with country feel. Close to state parks which is why we selected this location"
Restored 19th century farmhouse apartment 1- charming farmland and town culture!
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
10.0 out of 10, Exceptional, (6)
"My son and I stayed here for a week while he was attending a Pipe Band camp. The place was perfect!!! Clean, great location and super comfortable. The host responded very quickly when I texted with a question and also checked in through email to make sure everything was going well and that we were pleased. I would highly recommend this place. Thanks for a great stay!!!"
The price is SAR 413
SAR 881 total
includes taxes & fees
25 Sep - 26 Sep
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Farmhouse-Loft -48 Main Street, Lenox, MA
Dining
Farmhouse-Loft -48 Main Street, Lenox, MA
10.0 out of 10, Exceptional, (6)
"Absolutely wonderful location, the loft itself was amazing i think the online pictures did not do it justice, beautifully decorated, spacious, clean, close to main attractions , very comfortable setting, communication with owners was kind, thoughtful and helpful, would absolutely recomend."
Farmhouse-Loft -48 Main Street, Lenox, MA
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
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
Fully Redone Suite with master King Bed
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!"
Gorgeous 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
Comfy Cabin Decor with Ultra-Premium Bedding
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (2)
"Great location and host was friendly and very responsive. Kitchen has the basic necessities and the unit has plenty of extra blankets, and good quality towels and linens. Very convenient to the slopes, private parking is a big plus, and the property has lots of amenities for kids. Would definitely stay here again. "
The price is SAR 390
SAR 853 total
includes taxes & fees
25 Sep - 26 Sep
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Bridge Street Oasis
Interior
Bridge Street Oasis
The price is SAR 804
SAR 1,344 total
includes taxes & fees
30 Sep - 1 Oct
Bridge Street Oasis
2 bed room Apartment
Living area
2 bed room Apartment
The price is SAR 450
SAR 720 total
includes taxes & fees
29 Sep - 30 Sep
2 bed room Apartment
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
Living area
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Was a great spot to enjoy Jiminy Peak!"
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
Apartment in Gorgeous Stonybrook Farm
Apartment in Gorgeous Stonybrook Farm
9.4 out of 10, Exceptional, (44)
"This was a beautifully appointed property on an estate overlooking a pond. The apartment was spotless and the caretaker was most helpful when we needed anything. The rooms were well supplied and perfect for us. Thank you for letting us experience the quintessence of the Berkshires."
Apartment in Gorgeous Stonybrook Farm
Hip on Warren
Private kitchen
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 SAR 1,032
SAR 1,494 total
includes taxes & fees
25 Sep - 26 Sep
Hip on Warren
Elmhurst House - Gnd Floor - 3bd Catskill Mtn View
Property grounds
Elmhurst House - Gnd Floor - 3bd Catskill Mtn View
9.6 out of 10, Exceptional, (5)
"Had a great stay here for a couple of nights with some friends. The place was spacious and clean and the owners live right next door and were very nice and responsive. Would definitely stay here again!"
Elmhurst House - Gnd Floor - 3bd Catskill Mtn View
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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
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1714)
"Nice place. Pleasantly surprised how big the suite was. The whole place was very clean from the suite itself, the huge indoor pool and hot tub. The clerk that checked us in was very knowledgeable of the area and just a pleasant person. She is an older lady, I forget her name but she is a definite asset to this property! On the down side the path to the main office was not well lit but we used our flashlights. Also there isn't restaurants on site or groceries available. We had to travel 25...
The price is SAR 633
SAR 732 total
includes taxes & fees
24 Sep - 25 Sep
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (897)
"Was good everything "
The price is SAR 549
SAR 602 total
includes taxes & fees
26 Sep - 27 Sep
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (30)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
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 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.