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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 120 Apartments in Chatham with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Food and drink

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (22)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
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, (27)
"Clean, comfortable and great location."
51 Church Street, Lenox MA - One Bedroom Unit
All comforts of home
Fridge, microwave, oven, stovetop

All comforts of home

9.8 out of 10, Exceptional, (39)
"Absolutely beautiful, cozy, and quiet. Highly recommend and look forward to staying again in the future. "
The price is AED 400
AED 512 total
includes taxes & fees
18 May - 19 May
All comforts of home
Apartment In Historic 1785 Thomas Jenkins House
Fridge, microwave, oven, stovetop

Apartment In Historic 1785 Thomas Jenkins House

10.0 out of 10, Exceptional, (77)
"Wonderful property and close to everything!"
Apartment In Historic 1785 Thomas Jenkins House
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Living area

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
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, (28)
"Zero complaints. Perfect location"
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, (26)
"My family had a great ski weekend at Howard’s place. Everything was as described and the location could not be beat! Howard was an excellent host - super communicative and very prompt in responding to the few questions we had. We would absolutely stay here again. "
The price is AED 646
AED 1,284 total
includes taxes & fees
13 May - 14 May
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Elmhurst House - Gnd Floor - 3bd Catskill Mtn View
Outdoor dining

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
Downtown Hudson Apartment: Walk to Cafes & River!
Outdoor dining

Downtown Hudson Apartment: Walk to Cafes & River!

10.0 out of 10, Exceptional, (3)
"This apartment was in the most convenient location. Easy to walk to fabulous restaurants and shops. Amenities were plenty and the beds were so comfortable. I definitely would stay here again! Made our stay in Hudson so lovely!"
Downtown Hudson Apartment: Walk to Cafes & River!
Upstairs on Main with private bathroom
Property grounds

Upstairs on Main with private bathroom

9.2 out of 10, Wonderful, (32)
"The place is as described. Excellent location."
Upstairs on Main with private bathroom
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Living area

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
The price is AED 551
AED 804 total
includes taxes & fees
31 May - 1 Jun
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Hudson NY’S Country Serenity
Property grounds

Hudson NY’S Country Serenity

10.0 out of 10, Exceptional, (1)
"Quiet, private , comfortable and clean sanctuary! Highly recommend…!! "
Hudson NY’S Country Serenity
A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (23)
"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.
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Exterior

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

9.8 out of 10, Exceptional, (18)
"Great place to spend the new years holiday! Perfect location for skiing!"
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Property grounds

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. "
The price is AED 477
AED 976 total
includes taxes & fees
13 May - 14 May
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Black Bear Bungalow, Sheffield/Great Barrington/Ski Resorts
Fridge, microwave, oven, stovetop

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

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

9.6 out of 10, Exceptional, (30)
"Perfect 1 bedroom, ski in ski off , updated unit with great amenities! Owner super responsive and accommodating. Will definitely be back "
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Golf

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
2 bed room Apartment
Dining tables

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 353
AED 659 total
includes taxes & fees
19 May - 20 May
2 bed room Apartment
Hip on Warren
Smart TV

Hip on Warren

10.0 out of 10, Exceptional, (10)
"Loved our stay here! Great location and cute apartment. Would recommend to anyone visiting the town!"
Hip on Warren
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, (1804)
"The property was clean and the staff very accommodated."
The price is AED 512
AED 612 total
includes taxes & fees
13 May - 14 May
Vacation Village in the Berkshires
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
8.8 out of 10, Excellent, (11)
"We always live these cabins & we've been coming for years!"
The price is AED 643
AED 833 total
includes taxes & fees
28 May - 29 May
Postcard Cabins Eastern Catskills
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (929)
"Out dated not many resort like options "
The price is AED 488
AED 545 total
includes taxes & fees
17 May - 18 May
Jiminy Peak Mountain Resort
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: 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. All comforts of home: Located 8.8 mi/14.2 km away in Hudson. Amenities include private balconies. Access to a hot tub is available on site. 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. 51 Church Street, Lenox MA - One Bedroom Unit: It’s situated in Lenox, 15.9 mi/25.6 km from 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.