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Compare 123 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, (23)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

All comforts of home

9.8 out of 10, Exceptional, (41)
"Absolutely beautiful, cozy, and quiet. Highly recommend and look forward to staying again in the future. "
The price is AED 360
AED 468 total
includes taxes & fees
13 Jun - 14 Jun
All comforts of home

Apartment In Historic 1785 Thomas Jenkins House

10.0 out of 10, Exceptional, (80)
"Wonderful property and close to everything!"
Apartment In Historic 1785 Thomas Jenkins House

Charming 1-bedroom apartment in wonderful Lenox Dale

10.0 out of 10, Exceptional, (1)
"I was thru-hiking the AT and had to get out of some bad weather. This place isn’t trail adjacent but it was worth the cab ride. Quiet, clean, laundry, easy check-in, well-stocked amenities, comfortable bed. Much better option than nearby hotels. Lucky to have found it when I needed it. "
Charming 1-bedroom apartment in wonderful Lenox Dale

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (30)
"Clean, comfortable and great location."
51 Church Street, Lenox MA - One Bedroom Unit

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

9.4 out of 10, Exceptional, (61)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"Very clean and nicely decorated apartment in center of town. Great location. Really enjoyed our vacation."
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

2 bed room Apartment

10.0 out of 10, Exceptional, (2)
"It was definitely a great get away very quiet and peaceful location "
The price is AED 514
AED 853 total
includes taxes & fees
9 Jun - 10 Jun
2 bed room Apartment

Charming Claverack Retreat w/ Serene Deck!

9.6 out of 10, Exceptional, (5)
"Great location about 10 min from Warren Street, super relaxing and quite isolated from the main road."
Charming Claverack Retreat w/ Serene Deck!

1500 sqft private entrance with beautiful views of the Berkshire Mountains

10.0 out of 10, Exceptional, (41)
"Perfect get away, convenient to everything."
1500 sqft private entrance with beautiful views of the Berkshire Mountains

Elmhurst House - Gnd Floor - 3bd Catskill Mtn View

9.0 out of 10, Wonderful, (6)
"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

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

10.0 out of 10, Exceptional, (3)
"Condo in great location for skiing and really in good shape. Nicely decorated. Kids loved the moose toy. Kitchen had everything we needed. Perfect winter break for us. "
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

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

9.8 out of 10, Exceptional, (7)
"Everything was wonderful…"
The price is AED 426
AED 915 total
includes taxes & fees
11 Jun - 12 Jun
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

10.0 out of 10, Exceptional, (1)
"Lovely quiet spot with plenty of eating options around the area. Well maintained."
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts

A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.

10.0 out of 10, Exceptional, (24)
"We had a wonderful stay in this historic house and were overwhelmed with the kindness and generosity of our hosts. If we are ever in the area again, we will book again!"
A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.

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

9.0 out of 10, Wonderful, (2)
"Loved our short stay! Very clean, well maintained, and super cozy. Communication was very prompt and pleasant. Would definitely stay again! "
The price is AED 558
AED 1,079 total
includes taxes & fees
12 Jun - 13 Jun
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

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

Sweet 2-bedroom apartment on horse farm in Hillsdale with WiFi and AC

Sweet 2-bedroom apartment on horse farm in Hillsdale with WiFi and AC

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

10.0 out of 10, Exceptional, (7)
"We had a wonderful 3 day weekend! Perfect location for families."
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Restored 19th century farmhouse apartment 1- charming farmland and town culture!

9.6 out of 10, Exceptional, (14)
"This getaway was perfect. We loved the location, kitchen, cozy beds and most of all, the wildlife and farm animals. We will absolutely book this stay again!"
Restored 19th century farmhouse apartment 1- charming farmland and town culture!
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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Frequently asked questions

What's it like to stay at an apartment in Chatham?
There are plenty of places to stay in Chatham with 23 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. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 18 mi/29 km away in Lee. Private patios and fireplaces 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. Apartment In Historic 1785 Thomas Jenkins House: 12.7 mi/20.4 km away in Hudson.
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.