Old Chatham Holiday Rentals

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Holiday Rentals in Old Chatham

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

9.6 out of 10, Exceptional, (91)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2039)
"Really nice place at a reasonable price"
The price is AU$172
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (981)
"Staff was very nice and helpful. Property was a little bit outdated but very clean and functional. Surroundings are beautiful!!"
The price is AU$234
includes taxes & fees
19 Oct - 20 Oct
Jiminy Peak Mountain Resort

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (4)
"Perfect place for a relaxing getaway! We loved everything! "
The price is AU$166
includes taxes & fees
8 Oct - 9 Oct
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (131)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (124)
"Great stay!"
The price is AU$220
includes taxes & fees
7 Oct - 8 Oct
Micosta Leisure Inn

Taborton Harvest Boulder Pines Cabin in the woods

10.0 out of 10, Exceptional, (12)
"Such a sweet spot in the woods! Can’t wait to come back."
The price is AU$280
includes taxes & fees
7 Oct - 8 Oct
Taborton Harvest Boulder Pines Cabin in the woods

cozy retreat with modern amenties

2.0 star property
The price is AU$469
includes taxes & fees
7 Oct - 8 Oct
cozy retreat with modern amenties

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

Spacious 5-bedroom house in charming Lee with WiFi

The price is AU$1,256
includes taxes & fees
21 Oct - 22 Oct
Spacious 5-bedroom house in charming Lee with WiFi

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (30)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
The price is AU$1,702
includes taxes & fees
21 Oct - 22 Oct
Hancock Village Inn at Jiminy Peak

The Bluebirds Nest

7.8 out of 10, Good, (6)
"My family stays at a lot of VRBOs and I have never had a host as accommodating and patient as Antonio. He was quick to respond and even came to the VRBO when I locked myself out."
The price is AU$186
includes taxes & fees
7 Oct - 8 Oct
The Bluebirds Nest

The Rizzy Apartment

7.2 out of 10, Good, (7)
"Great time "
The price is AU$266
includes taxes & fees
15 Oct - 16 Oct
The Rizzy Apartment

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AU$726
includes taxes & fees
7 Oct - 8 Oct
Comfortable Berkshires retreat on mtn resort, SISO

Rose Cottage

9.2 out of 10, Wonderful, (9)
"It's so peaceful there. It was lovely."
Rose Cottage

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 AU$280
includes taxes & fees
7 Oct - 8 Oct
Taborton Harvest Timber Trails Unique cabin experience

NEW Cozy Apt Bright + Modern W/D

8.6 out of 10, Excellent, (24)
"Good location and well maintained "
The price is AU$298
includes taxes & fees
3 Nov - 4 Nov
NEW Cozy Apt Bright + Modern W/D

Mid-century Cozy Retreat W/D

8.0 out of 10, Very good, (6)
"Walking distance to everything!! "
The price is AU$348
includes taxes & fees
24 Oct - 25 Oct
Mid-century Cozy Retreat W/D

Chic Madison Parkview

9.6 out of 10, Exceptional, (27)
"the apartment was in a great location, easy check-in, very simple check-in"
The price is AU$268
includes taxes & fees
7 Oct - 8 Oct
Chic Madison Parkview
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

Find out more about Old Chatham

Everything you need to know about Old Chatham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Old Chatham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Old Chatham holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Old Chatham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Chatham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Old Chatham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Old Chatham holiday rentals we have selected for you start as low as AU$166 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Old Chatham rentals

At Expedia, we put the best Old Chatham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Old Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Old Chatham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Old Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Old Chatham?

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

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

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS: This highly rated holiday home rental in Old Chatham is located on a lake, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a patio, a garden and a library so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Old Chatham?

With 6 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Old Chatham like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Chatham. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for family gatherings.