Old Chatham Vacation Rentals

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Our top choices for Old Chatham vacation rentals

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (16 reviews)
"My whole experience was just what I needed! Im in love with this place inspired me and my dog was in heaven 💛 "
United States
Lea
The price is CA $136
CA $212 total
includes taxes & fees
May 28 - May 29
Taborton Harvest Boulder Pines Cabin in the woods

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (10 reviews)
"Healthy food too!"
United States
GEORGINA
The price is CA $148
CA $165 total
includes taxes & fees
Jun 7 - Jun 8
Huttopia Berkshires

Magic Forest Farm's Enchanted Cabin

Magic Forest Farm's Enchanted Cabin
Coeymans Hollow
9.4 out of 10, Exceptional, (9 reviews)
"Such a cute little cabin. Great place to get some rest to break up a long drive. "
United States
Anonymous traveller
The price is CA $191
CA $236 total
includes taxes & fees
May 28 - May 29
Magic Forest Farm's Enchanted Cabin

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley
Stottville
The price is CA $257
CA $505 total
includes taxes & fees
Jun 4 - Jun 5
Boho Hot Tub Cottage | Pet-Friendly | Hudson Valley

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is CA $135
CA $182 total
includes taxes & fees
May 26 - May 27
All comforts of home

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (32 reviews)
"The location was just what we were looking for, the cabin was cozy and clean, and the host was so helpful and welcoming!"
United States
Olivia C.
The price is CA $146
CA $194 total
includes taxes & fees
May 26 - May 27
All the comforts of home

Uncle Sam's Hideaway |Nearby Colleges & Hospital|Personal Workspace|Pet Friendly

Uncle Sam's Hideaway |Nearby Colleges & Hospital|Personal Workspace|Pet Friendly
Troy
9.2 out of 10, Wonderful, (15 reviews)
"Great place! Highly recommended if you are visiting Troy "
United States
Matthew B.
The price is CA $103
CA $416 total
includes taxes & fees
May 25 - May 26
Uncle Sam's Hideaway |Nearby Colleges & Hospital|Personal Workspace|Pet Friendly

Charles Cottage Near Warren St New Renovation

Charles Cottage Near Warren St New Renovation
Hudson
The price is CA $237
CA $742 total
includes taxes & fees
May 26 - May 27
Charles Cottage Near Warren St New Renovation

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 CA $217
CA $276 total
includes taxes & fees
May 26 - May 27
The Brooks Motel: Exceptional Suite

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 CA $176
CA $364 total
includes taxes & fees
May 27 - May 28
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,361 reviews)
"great stay. "
United States
John
The price is CA $119
CA $148 total
includes taxes & fees
May 25 - May 26
Vacation Village in the Berkshires

cozy retreat with modern amenties

cozy retreat with modern amenties
2.0 star property
Delmar
The price is CA $299
CA $426 total
includes taxes & fees
May 22 - May 23
cozy retreat with modern amenties

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, (12 reviews)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
United States
Una D.
The price is CA $187
CA $378 total
includes taxes & fees
May 26 - May 27
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
United States
Antonio S.
The price is CA $187
CA $378 total
includes taxes & fees
May 26 - May 27
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor

Albany Retreat- Free Breakfast & Parking Included

Albany Retreat- Free Breakfast & Parking Included
West End
6.4 out of 10, (7 reviews)
"Easy checkin"
United States
Jake Z.
The price is CA $74
CA $184 total
includes taxes & fees
May 27 - May 28
Albany Retreat- Free Breakfast & Parking Included

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is CA $187
CA $378 total
includes taxes & fees
May 26 - May 27
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is CA $269
CA $761 total
includes taxes & fees
May 22 - May 23
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.8 out of 10, Exceptional, (21 reviews)
"Great location! "
United States
shannon m.
The price is CA $187
CA $378 total
includes taxes & fees
May 26 - May 27
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
The price is CA $227
CA $423 total
includes taxes & fees
May 22 - May 23
2 Bed Berkshire Getaway @ Stephentown Hotel

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is CA $187
CA $378 total
includes taxes & fees
May 27 - May 28
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
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 Old Chatham Hotel Reviews

Find out more about Old Chatham

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Old Chatham. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Old Chatham?

Yes, we offer vacation rentals close to well known points of interest in Old Chatham, or you can choose a more remote option if you'd like a relaxing place to stay. Old Chatham is known for its museums.

What are some of the best vacation rentals that Old Chatham has to offer?

Incredible Estate: pool, pond, gym, arcade, trails & more! Ask about open dates!: Visitors like this Old Chatham vacation home rental. It is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a patio, a garden, and a library so you can immerse yourself in your vacation.

How many vacation rentals will I find in Old Chatham?

With 8 Expedia vacation rentals, you're sure to find just the right place for your Old Chatham stay.

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

Enjoy the area's cultural attractions such as Shaker Museum and Library, or get outdoors into nature at a spot like Kinderhook Lake. Queechy Lake and Martin Van Buren National Historic Site are a couple of places you'll find in the larger area.

What’s a vacation rental in Old Chatham like?

Vacation rentals are privately owned properties you can book for several days or longer in Old Chatham. Vacation rentals offer amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a small group gathering.