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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
In four months
23 Jan - 25 Jan

Apartments in Chatham

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Fridge, microwave, oven, stovetop

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (32)
"Perfect place for what we needed. Loved the location."
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
2 bed room Apartment
Dining tables

2 bed room Apartment

10.0 out of 10, Exceptional, (4)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
The price is AED 294
AED 595 total
includes taxes & fees
5 Oct - 6 Oct
2 bed room Apartment
51 Church Street, Lenox MA - One Bedroom Unit
Fridge, microwave, oven, stovetop

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (33)
"Clean, comfortable and great location."
51 Church Street, Lenox MA - One Bedroom Unit
Modern Copake Falls Getaway
Exterior

Modern Copake Falls Getaway

9.6 out of 10, Exceptional, (34)
"Great place with amazing views and super close to a ski resort highly recommend "
Modern Copake Falls Getaway
Downtown Gateway to the Berkshires. Walk to Everything.
Exterior detail

Downtown Gateway to the Berkshires. Walk to Everything.

2.0 star property
8.0 out of 10, Very Good, (1)
"This cute and cozy apartment was in an excellent location. We were the first guest to stay here and we had a few concerns: the chairs in the kitchen were broken as was a door frame. The command hooks fell off the several times. There was no place to hang clothes and shelves which held the dishes were dirty and dusty as well as appliances. Some coffee and Kleenex would have a nice. The place has the potential to be amazing with a little more attention to details. We have stayed in many, many...
Downtown Gateway to the Berkshires. Walk to Everything.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (68)
"Location cannot be outdone. This rental was spacious, well stocked, extremely clean, and a very responsive kind owner. Highly recommended:)"
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
All comforts of home
Property grounds

All comforts of home

9.8 out of 10, Exceptional, (48)
"Comfortable, quiet"
The price is AED 360
AED 486 total
includes taxes & fees
5 Oct - 6 Oct
All comforts of home
The Studio mini home away from home in the Berkshires
Outdoor dining

The Studio mini home away from home in the Berkshires

9.6 out of 10, Exceptional, (29)
"Great place to stay in Berkshires."
The Studio mini home away from home in the Berkshires
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.6 out of 10, Exceptional, (30)
"We really enjoyed our stay it was a very nice place for a family."
The price is AED 577
AED 1,190 total
includes taxes & fees
6 Oct - 7 Oct
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Apartment In Historic 1785 Thomas Jenkins House
Fridge, microwave, oven, stovetop

Apartment In Historic 1785 Thomas Jenkins House

10.0 out of 10, Exceptional, (87)
"Easy access to restaurants and shopping . Clean and nicely decorated. Apartment has everything we needed for a relaxing Stay."
Apartment In Historic 1785 Thomas Jenkins House
The Serendipity Spot
Property grounds

The Serendipity Spot

10.0 out of 10, Exceptional, (1)
"Very comfortable, soft bed, cute decor and very convenient location for Great Barrington and surrounding area. Owners are kind, ready to help whenever you need something. Overall this is a great place to stay and we highly recommend it to anyone spending some time in the area. "
The Serendipity Spot
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior

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

10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
The price is AED 408
AED 890 total
includes taxes & fees
6 Oct - 7 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Exterior

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

9.8 out of 10, Exceptional, (7)
"This property was awesome for our family! Quick walk to the Mountain and all the shops!!! Great family spot!!"
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Heart of Lenox!! - renovated downtown apartment
Exterior

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (71)
"Beautiful property in a perfect location for a girls ski weekend getaway! "
Heart of Lenox!! - renovated downtown apartment
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Interior

Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice apartment. Beautiful grounds and gardens. We enjoyed ourselves. It was a very comfy place to return to as we enjoyed Jacob's Pillow and our other explorations around the Berkshires. "
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Elmhurst House/ Town-House - Gnd Floor - 3bd Catskill Mtn View
Outdoor dining

Elmhurst House/ Town-House - Gnd Floor - 3bd Catskill Mtn View

9.2 out of 10, Wonderful, (7)
"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/ Town-House - Gnd Floor - 3bd Catskill Mtn View
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (9)
"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
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Fridge, microwave, oven, stovetop

1500 sqft private entrance with beautiful views of the Berkshire Mountains

10.0 out of 10, Exceptional, (46)
"Perfect get away, convenient to everything."
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain
TV, DVD player, books

Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain

10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
The price is AED 408
AED 890 total
includes taxes & fees
6 Oct - 7 Oct
Must See Jurassic Jiminy Suite Country Inn - Sleeps 4 Ski On/Off Mountain
The Brooks Motel: Exceptional Suite
TV, offices

The Brooks Motel: Exceptional Suite

9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
The price is AED 599
AED 765 total
includes taxes & fees
5 Oct - 6 Oct
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
"Great place! Food excellent ss well!"
Crystal 1-night trip
Posted 2 days ago
The Red Lion Inn

Frequently asked questions

What's it like to stay at an apartment in Chatham?
There are plenty of places to stay in Chatham with 24 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: Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located in Great Barrington, 16.7 mi/26.9 km from the heart of Chatham. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site. 2 bed room Apartment: Located 20.7 mi/33.4 km away in Albany. Free WiFi, private patios, and separate dining areas are included. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 18 mi/29 km away. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. The Studio mini home away from home in the Berkshires: 18 mi/28.9 km away in Lee. Amenities include private patios.
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.