Old Chatham Holiday Rentals

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Holiday Rentals in Old Chatham

Artists’ Hideaway in Old Chatham
The price is AU$697
includes taxes & fees
26 Oct - 27 Oct
Artists’ Hideaway in Old Chatham
Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is AU$560
includes taxes & fees
27 Oct - 28 Oct
Sugar Shack - 300 square feet of pure sweetness.
BLUSH: Boutique TINY home*private spa*walk to town
10.0 out of 10, Exceptional, (6)
"Perfect blend of decore, comfort, and function. We went to Tanglewood which was only a half hour away. Came back to hot tub and fire pit. Beds here are soooo comfy! This is our 2nd time here and won’t be our last."
United States
Melissa D.
The price is AU$560
includes taxes & fees
28 Oct - 29 Oct
BLUSH: Boutique TINY home*private spa*walk to town
HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (9)
"No stone left unturned. The hot tub was clean and perfectly situated. the house was clean, with very sweet finishing touches. Within walking distance to shops. Hosts were very responsive. I highly recommend."
United States
Jamie F.
The price is AU$640
includes taxes & fees
23 Oct - 24 Oct
HunnyHAUS: Deluxe TINY*private spa*walk to town
Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2092)
"Great place!"
United States
Nicole
The price is AU$174
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, (983)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
United States
Amy
The price is AU$240
includes taxes & fees
26 Oct - 27 Oct
Jiminy Peak Mountain Resort
Taborton Harvest Boulder Pines Cabin in the woods
10.0 out of 10, Exceptional, (12)
"Loved the earthiness and serenity of the cabin and great room. Everything built and made and maintained by the Adamos- truly a haven "
United States
Joanna R.
The price is AU$284
includes taxes & fees
23 Oct - 24 Oct
Taborton Harvest Boulder Pines Cabin in the woods
Chic Madison Parkview
9.6 out of 10, Exceptional, (27)
"the apartment was in a great location, easy check-in, very simple check-in"
United States
Catherine Patricia H.
The price is AU$272
includes taxes & fees
24 Oct - 25 Oct
Chic Madison Parkview
Micosta Leisure Inn
3.0 star property
9.2 out of 10, Wonderful, (127)
"Great stay!"
United States
Amiya
The price is AU$204
includes taxes & fees
21 Nov - 22 Nov
Micosta Leisure Inn
UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
United States
Robert
The price is AU$485
includes taxes & fees
24 Oct - 25 Oct
UNIQUE - 1BR Country Condo @ Jiminy Peak
All the comforts of home
9.2 out of 10, Wonderful, (26)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is AU$220
includes taxes & fees
23 Oct - 24 Oct
All the comforts of home
2 bed room Apartment
10.0 out of 10, Exceptional, (4)
"Clean rooms, comfortable beds. Easy access location. Quiet neighborhood. Would stay again."
United States
Sarah K.
The price is AU$277
includes taxes & fees
27 Oct - 28 Oct
2 bed room Apartment
Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is AU$344
includes taxes & fees
23 Oct - 24 Oct
Berkshires Apartment at the Stephentown Hotel
✨Historic Full Amenities 2BR Apt @ Downtown Albany
9.0 out of 10, Wonderful, (18)
"Good place to rest after an active day "
United States
Julie B.
The price is AU$310
includes taxes & fees
26 Oct - 27 Oct
✨Historic Full Amenities 2BR Apt @ Downtown Albany
Tiny Home w/ Hot Tub and Sunset View!
10.0 out of 10, Exceptional, (1)
"Very private and quiet, we had a wonderful time! Stars were very bright at night and we even heard coyotes in the distance! "
United States
Blake
The price is AU$159
includes taxes & fees
27 Oct - 28 Oct
Tiny Home w/ Hot Tub and Sunset View!
The Bluebirds Nest
7.6 out of 10, Good, (7)
"Close to downtown and local colleges. Host was quick to answer when we had a couple of questions. "
United States
Laura C.
The price is AU$187
includes taxes & fees
28 Oct - 29 Oct
The Bluebirds Nest
Home in Great Barrington
9.8 out of 10, Exceptional, (24)
"Enjoyed our stay!!!"
United States
Fred W.
The price is AU$380
includes taxes & fees
5 Nov - 6 Nov
Home in Great Barrington
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
United States
Una D.
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Charming 3-bedroom Cabin for nature lovers
8.0 out of 10, Very good, (1)
"Very nice place to stay for our 3 day hike on the AT. The view from the deck is amazing and the living room is huge with an old stone fireplace which we didn’t use because it was 90 degrees each day. The Mexican restaurant in town (Norte Azul) has an extensive menu and a good variety of beer on tap. Highly recommend visiting Mt Greylock in MA, about 30 mins away. It has an even better restaurant on top (you need reservations) and is right on the Appalachian Trail so you will meet all sorts on...
United States
John O.
The price is AU$456
includes taxes & fees
24 Oct - 25 Oct
Charming 3-bedroom Cabin for nature lovers
All comforts of home
9.8 out of 10, Exceptional, (49)
"Comfortable, quiet"
United States
Paul M.
The price is AU$206
includes taxes & fees
26 Oct - 27 Oct
All comforts of 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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Top Old Chatham Hotel Reviews

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$174 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.