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Compare 120 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, (19)
"We loved the location of the rental and how we could just walk to town, walk to church, walk the River walk. It was a perfect spot! Quiet neighborhood. We liked that! Lots of terrific little shops. We will definitely be back! "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (27)
"The property was pristine, spacious, and perfectly located. Everything was convenient and in order; parking was easy.Will plan to stay again."
51 Church Street, Lenox MA - One Bedroom Unit

All comforts of home

9.8 out of 10, Exceptional, (38)
"The experience here was amazing and so very comfortable. I appreciated the amenities on the property, and I can't wait to come back!"
The price is AED 400
AED 512 total
includes taxes & fees
17 Apr - 18 Apr
All comforts of home

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

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

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

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 1,187 total
includes taxes & fees
20 Apr - 21 Apr
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

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

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!

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

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
The price is AED 551
AED 800 total
includes taxes & fees
16 Apr - 17 Apr
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

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.

10.0 out of 10, Exceptional, (23)
"This place was absolutely what I needed! Growing up in Columbia County it reminded me of my home in Glenco Mills. I choose this particular area, because is was close to sis in Valatia, best buddy in Ghent, and another buddy 4 miles away. Hudson is where I went to school and has changed so much?!?!?I still love that little city. Could have stayed with friends and family, but I needed time for me, to roll on the beautiful country roads, and admire where I once lived The hosts where absolutely...
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

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."
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, (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 856 total
includes taxes & fees
16 Apr - 17 Apr
Gorgeous 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

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 856 total
includes taxes & fees
16 Apr - 17 Apr
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

10.0 out of 10, Exceptional, (41)
"My husband and I stayed at this clean, spacious, and well-equipped apartment adjacent to the hosts' home for three nights to visit nearby attractions in Lenox, Pittsfield, Great Barrington, and Stockbridge. It was a wonderful property and the hosts couldn't have been nicer. We especially loved the gift basket prepared with some of their favorite area treats. Communication about the check-in/check-out process was simple. FYI for future travelers: there are no bathroom toiletries provided so...
1500 sqft private entrance with beautiful views of the Berkshire Mountains

2 bed room Apartment

The price is AED 353
AED 659 total
includes taxes & fees
16 Apr - 17 Apr
2 bed room Apartment

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
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, (1797)
"The location to jimney peak was great."
The price is AED 400
AED 479 total
includes taxes & fees
16 Apr - 17 Apr
Vacation Village in the Berkshires

Postcard Cabins Eastern Catskills

2.0 star property
8.4 out of 10, Very Good, (8)
"We always live these cabins & we've been coming for years!"
The price is AED 735
AED 932 total
includes taxes & fees
21 Apr - 22 Apr
Postcard Cabins Eastern Catskills

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Lovely caring owner. Beautiful room Hope to stay there again!"
The price is AED 477
AED 515 total
includes taxes & fees
29 Apr - 30 Apr
Micosta Leisure Inn
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: Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Situated in Lee, 18 mi/29 km from the heart of Chatham. Includes private patios and fireplaces. 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. 51 Church Street, Lenox MA - One Bedroom Unit: It’s located in Lenox, 15.9 mi/25.6 km away. Farmhouse-Loft -48 Main Street, Lenox, MA: 15.9 mi/25.6 km away in Lenox. Amenities include separate dining areas. All comforts of home: Located in Hudson, 8.8 mi/14.2 km from Chatham. Includes private balconies. Access to a hot tub is available on site.
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.