North Chatham Holiday Rentals

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Holiday Rentals in North Chatham

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1863)
"Very nice places "
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (947)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is NZ$333
includes taxes & fees
13 July - 14 July
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (106)
"We had an excellent stay, and would certainly book this place again!"
The price is NZ$234
includes taxes & fees
13 July - 14 July
Micosta Leisure Inn

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (11)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is NZ$274
includes taxes & fees
13 July - 14 July
Taborton Harvest Boulder Pines Cabin in the woods

cozy retreat with modern amenties

2.0 star property
The price is NZ$517
includes taxes & fees
11 July - 12 July
cozy retreat with modern amenties

Taborton Harvest Timber Trails Unique cabin experience

10.0 out of 10, Exceptional, (1)
"The cabin was exactly what my daughter and I were looking for. Everything was clean, organized and family friendly. A bonus was the property connects to Bessie Woods and we were able to go for a hike on the trails without even having to leave the property. If you love quiet and the sounds of nature, this is the perfect place for you. We can’t wait to stay there again soon."
The price is NZ$296
includes taxes & fees
14 July - 15 July
Taborton Harvest Timber Trails Unique cabin experience

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

10.0 out of 10, Exceptional, (163)
"We had a fabulous time staying at the property. The game room and karaoke setup was amazing. Enjoyed cooking pizza and the outdoor kitchen. Will definitely look to book again."
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (144)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

Chic Madison Parkview

9.8 out of 10, Exceptional, (21)
"the apartment was in a great location, easy check-in, very simple check-in"
The price is NZ$321
includes taxes & fees
22 July - 23 July
Chic Madison Parkview

Charming 3-bedroom Cabin for nature lovers

The price is NZ$564
includes taxes & fees
12 July - 13 July
Charming 3-bedroom Cabin for nature lovers

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (7)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

5 STAR ESTATE: POOL, POND, ARCADE, GYM, TRAILS! DON'T MISS OUT! JULY 13-20 OPEN!

9.6 out of 10, Exceptional, (87)
"Our group had a great time. The place is a bit dated but has room for plenty of people."
5 STAR ESTATE: POOL, POND, ARCADE, GYM, TRAILS! DON'T MISS OUT! JULY 13-20 OPEN!

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is NZ$1,833
includes taxes & fees
21 July - 22 July
Hancock Village Inn at Jiminy Peak

Watervliet Retreat

10.0 out of 10, Exceptional, (4)
"Perfect property for more than the average 2 people in a hotel room. Clean, quaint, adorable and a short few minutes drive from RPI. Area was safe with all the things we needed to make our stay comfortable. The host was easy to reach and very responsive and amenable. "
Watervliet Retreat

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (58)
"We had a wonderful time and loved the house! We will definitely be back!"
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10.0 out of 10, Exceptional, (121)
"Had an amazing weekend in this beautiful cabin! Highly recommend staying here! Great host, amazing views, beautiful property!"
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

The Rizzy Apartment

7.2 out of 10, Good, (5)
"Great time "
The price is NZ$361
includes taxes & fees
21 July - 22 July
The Rizzy Apartment

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.
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

Can I find holiday rentals in North Chatham?

Yes, there are holiday rentals close to the most popular sights in North Chatham, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that North Chatham has to offer?

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!: This holiday home rental outside of North Chatham is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of books in this rental home to help you unwind.

How many holiday rentals will I find in North Chatham?

With 3 Expedia holiday rentals, you're guaranteed to find just the right place for your North Chatham stay.

What’s there to see and do in North Chatham?

Explore the area and family-friendly sights such as Destroyer Escort Historical Museum, or get out into nature at a spot like Kinderhook Lake. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the wider area.

What’s a holiday rental in North Chatham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in North Chatham. Holiday rentals offer amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a clean environment, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family trips or small group gatherings.