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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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

9.4 out of 10, Exceptional, (15)
"We had a great time and enjoy staying here so much!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
All comforts of home
Fridge, microwave, oven, stovetop

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
25 Mar - 26 Mar
All comforts of home
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)
"Great location. Well appointed. Pictures don’t really do this place justice. "
51 Church Street, Lenox MA - One Bedroom Unit
Apartment In Historic 1785 Thomas Jenkins House
Fridge, microwave, oven, stovetop

Apartment In Historic 1785 Thomas Jenkins House

10.0 out of 10, Exceptional, (75)
"We stayed there for our 45th anniversary trip and had never been to Hudson. This place was absolutely perfect. It was easy to walk everywhere so location was amazing. The apartment itself was bright and clean. The kitchen very well supplied and plenty of towels. We’d highly recommend! "
Apartment In Historic 1785 Thomas Jenkins House
Upstairs on Main with private bathroom
Property grounds

Upstairs on Main with private bathroom

9.2 out of 10, Wonderful, (32)
"We enjoyed our stay in this great place! cute little upstairs apartment with a great use of space and perfect for getting around the area. We got the benefit of a beautiful snow storm too (and the walk and parking area were shoveled when we woke up which was nice!) thanks again."
Upstairs on Main with private bathroom
Hip on Warren
Smart TV

Hip on Warren

10.0 out of 10, Exceptional, (9)
"Apartment is adorable and right on Warren that has everything you could want for a quick visit to upstate NY. Restaurants , stores of all kinds and great coffee shops and bars. "
Hip on Warren
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Exterior

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

10.0 out of 10, Exceptional, (23)
"The condo worked for our family of four. Really convenient to all the fun and amenities at Jiminy Peak and easy access to the condo from the parking lot made moving ski equipment really easy. The condo itself could use a refresh and a deep clean but otherwise it was adequate. "
The price is AED 382
AED 844 total
includes taxes & fees
25 Mar - 26 Mar
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
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)
"Perfect location. Walking distance. Brand new apartment. "
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
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)
"The place is great, it needed a good sweeping. But when the saw the listing it stated there was a hot tub. Upon arriving we found there was no hot tub. The owner said he probably put that by accident. Which we found frustrating because it was one the reasons we chose this location.The communication was okay, it could’ve been better."
Elmhurst House - Gnd Floor - 3bd Catskill Mtn View
Restored 19th century farmhouse apartment 2 -charming farmland and town culture!
Property grounds

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!
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (25)
"Super convenient - just steps to the lift, right in the middle of resort. Can walk to lifts, the lodge ski school and restaurants. Condo has everything you need for for fun family weekend!Teen boys had lots of freedom and could come And go for night skiing on their own!Def renting from Howie again!! "
The price is AED 577
AED 1,171 total
includes taxes & fees
25 Mar - 26 Mar
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
Heart of Lenox!! - renovated downtown apartment
Flat-screen TV

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (68)
"The place was beautiful and comfortable. Everything was new and clean. Loved the location. Thanks again."
Heart of Lenox!! - renovated downtown apartment
Downtown Hudson Apartment: Walk to Cafes & River!
Outdoor dining

Downtown Hudson Apartment: Walk to Cafes & River!

10.0 out of 10, Exceptional, (2)
"Great little place! Well equipped with everything we needed. Would stay at again…easy for visiting family nearby."
Downtown Hudson Apartment: Walk to Cafes & River!
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
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)
"Planned on a Thursday. Arrived late Friday, skied Sat, home early Sun. All fell into place quickly and without much "research". Turned out to be an amazing trip."
The price is AED 382
AED 844 total
includes taxes & fees
25 Mar - 26 Mar
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 382
AED 844 total
includes taxes & fees
25 Mar - 26 Mar
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
Fridge, microwave, stovetop, coffee/tea maker

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
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 "
The price is AED 382
AED 844 total
includes taxes & fees
25 Mar - 26 Mar
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
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
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"Very nice accomodations, more like a mini apartment than a motel room. "
The price is AED 474
AED 560 total
includes taxes & fees
25 Mar - 26 Mar
Vacation Village in the Berkshires
Postcard Cabins Eastern Catskills
Exterior

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 735
AED 793 total
includes taxes & fees
25 Mar - 26 Mar
Postcard Cabins Eastern Catskills
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 547
AED 600 total
includes taxes & fees
2 Apr - 3 Apr
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: Situated in Great Barrington, 16.7 mi/26.9 km from the heart of Chatham. Includes free WiFi, separate dining areas, and Smart TVs. 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: 18 mi/29 km away in Lee. Private patios and fireplaces are included. The Studio mini home away from home in the Berkshires: It’s located in Lee, 18 mi/28.9 km from Chatham. Includes 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.