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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, (20)
"Walkable to the heart of GB, and all the restaurants/bars you need, while still in a quiet part of town. Outside temps were in the 20’s/30’s all week, and the house heated up quickly. The entire house is cozy, furniture is comfortable. The mattress in the upstairs bedroom isn’t the best but was good enough for the week. The bathroom is updated and water gets hot quickly. Loved our stay, will be repeat guests and highly recommend to anyone needing a place near the town center. "
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
3 May - 4 May
All comforts of home

Apartment In Historic 1785 Thomas Jenkins House

10.0 out of 10, Exceptional, (77)
"The place was immaculate. My brother stayed there. He complains about everything. He loved it and his very picky self found everything perfect. "
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

9.6 out of 10, Exceptional, (26)
"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 661
AED 1,294 total
includes taxes & fees
1 May - 2 May
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, (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

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
31 May - 1 Jun
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 470
AED 970 total
includes taxes & fees
1 May - 2 May
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 470
AED 970 total
includes taxes & fees
1 May - 2 May
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

10.0 out of 10, Exceptional, (1)
"It was definitely a great get away very quiet and peaceful location "
The price is AED 353
AED 662 total
includes taxes & fees
5 May - 6 May
2 bed room Apartment

Hip on Warren

10.0 out of 10, Exceptional, (10)
"The apartment was as described and perfect for a weekend getaway! "
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, (1802)
"Great property"
The price is AED 434
AED 516 total
includes taxes & fees
6 May - 7 May
Vacation Village in the Berkshires

Postcard Cabins Eastern Catskills

2.0 star property
8.6 out of 10, Excellent, (10)
"A must visit!! "
The price is AED 643
AED 833 total
includes taxes & fees
1 May - 2 May
Postcard Cabins Eastern Catskills

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (96)
"Lovely, and quiet, with water nearby. Everything was nice and worked, and owner responded to communication quickly. Will visit again! "
The price is AED 477
AED 515 total
includes taxes & fees
13 May - 14 May
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: Located in Lee, 18 mi/29 km from the heart of Chatham. Includes private patios and fireplaces. Access to onsite laundry facilities is available 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. Access to onsite laundry facilities is available on site. 51 Church Street, Lenox MA - One Bedroom Unit: It’s located in Lenox, 15.9 mi/25.6 km away. 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. Apartment In Historic 1785 Thomas Jenkins House: It’s situated in Hudson, 12.7 mi/20.4 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.