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Apartments in Chatham for Rent

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Chatham apartments

Property grounds

1. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (56 reviews)
"👍"
United States
Mike
The price is ￥15,658
￥21,110 total
includes taxes & fees
Aug 3 - Aug 4
All comforts of home
Coffee/tea maker, fridge, microwave, oven

2. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.0 out of 10, Very Good, (1 review)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
Cozy 1-bedroom studio in serene Great Barrington with AC
Desk, iron/ironing board, WiFi, bed sheets

3. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (6 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is ￥25,218
￥31,819 total
includes taxes & fees
Aug 2 - Aug 3
The Brooks Motel: Exceptional Suite
Gift shop

4. Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Gift shop

5. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is ￥22,665
￥45,105 total
includes taxes & fees
Aug 3 - Aug 4
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Beach

6. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (4 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is ￥22,298
￥43,509 total
includes taxes & fees
Aug 4 - Aug 5
Berkshires Apartment at the Stephentown Hotel
Indoor pool, a heated pool

7. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is ￥20,398
￥42,217 total
includes taxes & fees
Aug 3 - Aug 4
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Pool

8. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.0 out of 10, Wonderful, (4 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is ￥35,753
￥66,322 total
includes taxes & fees
Aug 30 - Aug 31
Hudson NY’S Country Serenity Guest Suite.
Pool

9. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
The price is ￥23,143
￥45,640 total
includes taxes & fees
Aug 5 - Aug 6
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Property grounds

10. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is ￥22,665
￥45,105 total
includes taxes & fees
Aug 3 - Aug 4
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Pool

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

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is ￥20,398
￥42,217 total
includes taxes & fees
Aug 3 - Aug 4
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Desk, iron/ironing board, WiFi, bed sheets

12. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is ￥23,942
￥30,390 total
includes taxes & fees
Aug 2 - Aug 3
The Brooks Motel: Exceptional Suite
TV, fireplace, DVD player

13. Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very Good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is ￥36,072
￥66,321 total
includes taxes & fees
Aug 31 - Sep 1
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Beach

14. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very Good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is ￥24,580
￥46,774 total
includes taxes & fees
Aug 2 - Aug 3
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Gift shop

15. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is ￥22,665
￥45,105 total
includes taxes & fees
Aug 3 - Aug 4
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Pool

16. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (35 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is ￥36,056
￥65,948 total
includes taxes & fees
Aug 1 - Aug 2
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Smart TV

17. 2 bed room Apartment

2 bed room Apartment
South End
8.4 out of 10, Very Good, (12 reviews)
"Great communication and lovely place "
United States
Jude M.
The price is ￥15,801
￥29,476 total
includes taxes & fees
Aug 11 - Aug 12
2 bed room Apartment
TV, fireplace, DVD player, offices

18. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Hancock
9.6 out of 10, Exceptional, (4 reviews)
"Excellent instructions by the owner for the check in process, which was easy. The room was beautiful and very clean, and exactly as advertised. We would absolutely recommend and stay again!!"
United States
Chad J.
The price is ￥28,443
￥54,413 total
includes taxes & fees
Aug 3 - Aug 4
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Outdoor dining

19. Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is ￥20,398
￥42,217 total
includes taxes & fees
Aug 3 - Aug 4
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Pool

20. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is ￥22,665
￥45,105 total
includes taxes & fees
Aug 3 - Aug 4
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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Top Chatham Hotel Reviews

The Red Lion Inn

The Red Lion Inn

8/10 Good
"I gotta admit, I was nervous about staying at the Red Lion Inn. I knew it was popular, but I stayed in their "sister" place (the Little Lion) once because it was the only available hotel room in the area at short notice and that place is a DISASTER. However, now I understand why people who love the Red Lion Inn LOVE the Red Lion Inn. It's not pristine & shiny in a new hotel kinda way. But it's also the exact opposite of a bland, chain hotel with no character or interest. 250y of history pours out of every inch of this place, and in a good way. I didn't get a chance to take advantage of the gym, pool, or other amenities, though did eat in the courtyard one lunchtime and that was good. The staff are very attentive and appear to take real pride in working in such an iconic hotel. My only criticism is that I don't think the cleaning is quite up to scratch. Harder to clean 250yo hotel with rugs over ancient wood floors than a new construction with LVP, but findings long blonde hairs on my hotel room wasn't something I enjoyed (my entire family is either red or brunette). Would I stay there again? Yes. Room prices in the summer are insane, like most places in the Berkshires, but that's when I have to go to the Berkshires, so if they don't get my business in the future, it'll be because there are no rooms available or for some reason a different town is a better choice of location, not because I don't want to stay here. 1 word of warning: have dog? Call to make your reservation."
Carol 2-night trip
Posted 1 hour ago
The Red Lion Inn

Find out more about Chatham

Chatham Apartments information

Number of reviews
218
Accommodation
111 Apartments
Lowest Price
￥21,110
Highest Price
￥66,322

Frequently asked questions

What's it like to stay at an apartment in Chatham?
You'll find 5 apartments to choose from in Chatham for your trip.
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?
Listed below are some of the favorite apartments in the area to choose from: Cozy 1-bedroom studio in serene Great Barrington with AC: Located 16.7 mi/26.9 km away in Great Barrington. Free WiFi, private balconies, and Smart TVs are included. Access to onsite laundry facilities is available on site. Apartment In Historic 1785 Thomas Jenkins House: It's located in Hudson, 12.7 mi/20.4 km away. Hotel-like Balcony Suite—View—Private Wing&Entry—Ensuite Bath—Walk to Town, Lake: It's located in Great Barrington, 16.3 mi/26.2 km from Chatham. Includes free WiFi, private balconies, and Smart TVs.
How many apartments will I find in Chatham?
Expedia has 5 apartments to book in 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 Kinderhook Lake. The Mac-Haydn Theatre and Hudson Chatham Winery 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.