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25 Jul - 27 Jul
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Apartments in Chatham

Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge
Living area

Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge

Spacious 3-bedroom apartment with WiFi, AC on Main Street Stockbridge
Apartment In Historic 1785 Thomas Jenkins House
Fridge, microwave, oven, stovetop

Apartment In Historic 1785 Thomas Jenkins House

10.0 out of 10, Exceptional, (84)
"Wonderful property and close to everything!"
Apartment In Historic 1785 Thomas Jenkins House
Hudson NY’S Country Serenity Guest Suite.
Property grounds

Hudson NY’S Country Serenity Guest Suite.

10.0 out of 10, Exceptional, (1)
"Quiet, private , comfortable and clean sanctuary! Highly recommend…!! "
Hudson NY’S Country Serenity Guest Suite.
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Fridge, microwave, oven, stovetop

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (26)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Charming Apartment In Berkshire Victorian Home
Interior

Charming Apartment In Berkshire Victorian Home

8.0 out of 10, Very Good, (9)
"This adorable place is central to Pittsfield and made it really easy for my daughter and I go get where we needed to be. It’s a clean, great space. We’ll definitely be back!"
Charming Apartment In Berkshire Victorian Home
All comforts of home
Property grounds

All comforts of home

9.8 out of 10, Exceptional, (45)
"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 SAR 368
SAR 478 total
includes taxes & fees
20 Jul - 21 Jul
All comforts of home
Downtown Gateway to the Berkshires. Walk to Everything.
Microwave, oven

Downtown Gateway to the Berkshires. Walk to Everything.

2.0 star property
8.0 out of 10, Very Good, (1)
"This cute and cozy apartment was in an excellent location. We were the first guest to stay here and we had a few concerns: the chairs in the kitchen were broken as was a door frame. The command hooks fell off the several times. There was no place to hang clothes and shelves which held the dishes were dirty and dusty as well as appliances. Some coffee and Kleenex would have a nice. The place has the potential to be amazing with a little more attention to details. We have stayed in many, many...
Downtown Gateway to the Berkshires. Walk to Everything.
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, (24)
"Wonderful place to stay. Highly recommend. Like something out of a hallmark movie"
A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

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

9.4 out of 10, Exceptional, (63)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Spacious 3-bedroom apartment in Catskill village - walkable to area attractions
Private kitchen

Spacious 3-bedroom apartment in Catskill village - walkable to area attractions

The price is SAR 1,196
SAR 2,033 total
includes taxes & fees
7 Aug - 8 Aug
Spacious 3-bedroom apartment in Catskill village - walkable to area attractions
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (8)
"Emmy is a great hostess. The apartment is nicely appointed and in a great location to restaurants and shops and attractions in the Berkshires. "
Gateway to the Berkshires - Renovated downtown apartment
Charming 1-bedroom apartment in wonderful Lenox Dale
Exterior

Charming 1-bedroom apartment in wonderful Lenox Dale

10.0 out of 10, Exceptional, (6)
"Very comfortable, spacious, and well equipped. A perfect place to stay while attending a wedding in Lenox"
Charming 1-bedroom apartment in wonderful Lenox Dale
The Brooks Motel: Exceptional Suite
TV, offices

The Brooks Motel: Exceptional Suite

7.0 out of 10, Good, (4)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
The price is SAR 596
SAR 753 total
includes taxes & fees
20 Jul - 21 Jul
The Brooks Motel: Exceptional Suite
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Exterior

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

9.8 out of 10, Exceptional, (7)
"This property was awesome for our family! Quick walk to the Mountain and all the shops!!! Great family spot!!"
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
Terrace/patio

Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

9.6 out of 10, Exceptional, (24)
"Peaceful property, very responsive owners. The home was impeccably clean. Perfect for 2 adults, 1 teen, and a medium sized dog. "
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
Walk to Dtwn Hudson: Cozy Upstate Apartment
Property grounds

Walk to Dtwn Hudson: Cozy Upstate Apartment

2.0 out of 10, (1)
"The property was misrepresented as two bedroom when only one. The location of the second bed does not have a door nor a closet. A desk was listed and not in the apartment. I used the apartment for remote work and needed a desk. Many of the power outlets did not work. The lamps in the bedroom with a door did not have light bulbs.When the oven and stove did not work, the owner responded 6 hours later after I notified VRBO and Evolve. She told me the stove needed to be plugged in. This required me...
Walk to Dtwn Hudson: Cozy Upstate Apartment
Heart of Lenox!! - renovated downtown apartment
Exterior

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (69)
"Beautiful property in a perfect location for a girls ski weekend getaway! "
Heart of Lenox!! - renovated downtown apartment
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Exterior

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. "
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
Interior

Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails

2.0 star property
10.0 out of 10, Exceptional, (1)
"This location was perfect for hiking the AT. The trail is only a few feet from the front door. The backyard is very nice, and they had chairs and tables to sit out. The apartment was a nice size for two people. There was no tv, so we used our computer. The kitchen was great to have since we didn't plan on eating out every night. There are plenty of restaurants in the area. The hosts were great and very responsive. The fall colors made the trip extra special."
Remodeled Unit #1, 7 min to Great Barrington, 12 min to Ski Resorts & Trails
The Penthouse, Downtown Lenox by Evergreen Home
3 bedrooms, desk, iron/ironing board, travel crib

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (8)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home
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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Frequently asked questions

What's it like to stay at an apartment in Chatham?
There are plenty of places to stay in Chatham with 24 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: Hudson NY'S Country Serenity Guest Suite.: Situated in Hudson, 9.8 mi/15.7 km from the heart of Chatham. Includes free WiFi and Smart TVs. Apartment In Historic 1785 Thomas Jenkins House: Located 12.7 mi/20.4 km away in Hudson. 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. Charming Apartment In Berkshire Victorian Home: 18.3 mi/29.4 km away in Pittsfield. Private balconies and sofa beds are included. 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 Kinderhook Lake. 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.