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Compare 97 Apartments in Chatham with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (13)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

10.0 out of 10, Exceptional, (1)
The price is AED 577
AED 1,091 total
includes taxes & fees
25 Feb - 26 Feb
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

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

10.0 out of 10, Exceptional, (5)
"Condo was conveniently located at the base of the mountain. Had everything you would need for a quick weekend getaway. Owner was available for any questions."
The price is AED 577
AED 1,091 total
includes taxes & fees
25 Feb - 26 Feb
1st Floor 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

10.0 out of 10, Exceptional, (4)
"Perfect place to stay for a quick ski trip. Host was super helpful & accommodating. Suite was comfortable & well-equipped. We’ll be back "
The price is AED 577
AED 1,091 total
includes taxes & fees
24 Feb - 25 Feb
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect location. Walking distance. Brand new apartment. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

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 "
The price is AED 577
AED 1,091 total
includes taxes & fees
25 Feb - 26 Feb
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (7)
"This is the second year we had our girls weekend at the Penthouse and it did not disappoint. The place is updated, very clean, and in a great location! Only suggestion would to get a nice big sectional couch! We had 8 people and not enough comfy seating. But beautiful apartment!! "
The Penthouse, Downtown Lenox by Evergreen Home

Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

2.0 star property
9.4 out of 10, Exceptional, (3)
"Great stay "
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

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

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (24)
"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 768
AED 1,422 total
includes taxes & fees
25 Feb - 26 Feb
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

All comforts of home

9.8 out of 10, Exceptional, (37)
"Absolutely beautiful, cozy, and quiet. Highly recommend and look forward to staying again in the future. "
The price is AED 400
AED 506 total
includes taxes & fees
24 Feb - 25 Feb
All comforts of home

Restored 19th century farmhouse apartment 2 -charming farmland and town culture!

9.4 out of 10, Exceptional, (13)
"Cute little apartment in a cute and quiet street. Loved our stay!"
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!

Modern Copake Falls Getaway

9.6 out of 10, Exceptional, (31)
"Cozy modern apartment with great views. Very close to Catamount and a short drive to Great Barrington. Michael was a great host."
Modern Copake Falls Getaway

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

9.8 out of 10, Exceptional, (17)
"The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again."
The price is AED 577
AED 1,091 total
includes taxes & fees
25 Feb - 26 Feb
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

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 577
AED 1,091 total
includes taxes & fees
25 Feb - 26 Feb
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

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

2 bed room Apartment

The price is AED 441
AED 698 total
includes taxes & fees
1 Mar - 2 Mar
2 bed room Apartment

Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

9.6 out of 10, Exceptional, (23)
"We were treated with such kindness and understanding of our situation. We would gladly recommend Alisha to anyone wanting to stay at their property. In fact, we are going back in May. "
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

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

9.4 out of 10, Exceptional, (60)
"The property was fine for our purposes of visiting family. If we needed to cook, it would have been quite difficult, though not totally impossible. The furniture was comfortable and the rooms, except the kitchen, had plenty of space. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
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, (1766)
"Great place for a family vacation. Property very clean, quiet, and well organized "
The price is AED 400
AED 476 total
includes taxes & fees
4 Mar - 5 Mar
Vacation Village in the Berkshires

Postcard Cabins Eastern Catskills

2.0 star property
8.0 out of 10, Very Good, (4)
"We love our Bartow cabin, it was so cozy and relaxing for us. A perfect getaway from the city life. Will definitely stay again. "
The price is AED 643
AED 694 total
includes taxes & fees
25 Feb - 26 Feb
Postcard Cabins Eastern Catskills

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is AED 438
AED 489 total
includes taxes & fees
24 Feb - 25 Feb
The Ponds at Foxhollow
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 26 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: 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor: Located in Hancock, 20.4 mi/32.8 km from the heart of Chatham. Includes sofa beds. A fitness center and an indoor pool are on site. Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located 16.7 mi/26.9 km away in Great Barrington. Free WiFi, separate dining areas, and Smart TVs are included. 1500 sqft private entrance with beautiful views of the Berkshire Mountains: It’s situated in Lee, 18.4 mi/29.6 km away. Includes free WiFi, private patios, and Smart TVs. Downtown Hudson Apartment: Walk to Cafes & River!: 12.8 mi/20.6 km away in Hudson. 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.