Old Chatham Holiday Rentals

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Holiday Rentals in Old Chatham

Artists’ Hideaway in Old Chatham

Old Chatham
The price is NZ$839
includes taxes & fees
12 Nov - 13 Nov
Artists’ Hideaway in Old Chatham

Sugar Shack - 300 square feet of pure sweetness.

2.0 star property
Chatham
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 NZ$640
includes taxes & fees
11 Nov - 12 Nov
Sugar Shack - 300 square feet of pure sweetness.

BLUSH: Boutique TINY home*private spa*walk to town

Chatham
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 NZ$642
includes taxes & fees
17 Nov - 18 Nov
BLUSH: Boutique TINY home*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

Chatham
10.0 out of 10, Exceptional, (9)
"We had the best time here. The house is even cuter and cozier in person (which says a lot because the pictures are great!). The hot tub was a great luxury and the house is literally a 3 minute walk to town. So convenient! We also had a fire in the Viking tent one night which was fun. Heidi was super helpful and quick to respond to any queries during our stay. She even left rose petals on the bed and a bottle of Prosecco chilling in the fridge for us upon our arrival. I would stay here again in a...
United States
Megan H.
The price is NZ$734
includes taxes & fees
16 Nov - 17 Nov
HunnyHAUS: Deluxe TINY*private spa*walk to town

Jiminy Peak Mountain Resort

3.0 star property
Hancock
8.2 out of 10, Very good, (984)
"It was a fun place to stay. Rooms were clean and dishes well stocked in the kitchenette. "
United States
Sandhya
The price is NZ$296
includes taxes & fees
10 Nov - 11 Nov
Jiminy Peak Mountain Resort

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2126)
"Clean and great pool and hot tub facilities "
United States
Alyce
The price is NZ$202
includes taxes & fees
12 Nov - 13 Nov
Vacation Village in the Berkshires

Micosta Leisure Inn

3.0 star property
Hudson
9.2 out of 10, Wonderful, (129)
"It's a beautiful little place with a wonderful owner. Rooms are clean and a good price"
United States
Gail
The price is NZ$235
includes taxes & fees
21 Nov - 22 Nov
Micosta Leisure Inn

The Ponds at Foxhollow

3.0 star property
Lenox
8.6 out of 10, Excellent, (132)
"Perfect location "
United States
krystle
The Ponds at Foxhollow

Taborton Harvest Boulder Pines Cabin in the woods

Sand Lake
10.0 out of 10, Exceptional, (13)
"We LOVED our stay! Cabins were spotless and the main building was just great! Waking up to a picture window behind us with all the fall colors in their glory was such a highlight. "
United States
Barb W.
The price is NZ$326
includes taxes & fees
10 Nov - 11 Nov
Taborton Harvest Boulder Pines Cabin in the woods

Charming 1-bedroom apartment with AC, WiFi in welcoming Albany

2.0 star property
Pine Hills
10.0 out of 10, Exceptional, (1)
"Easy to get around this quiet neighborhood."
United States
Mary Ann C.
The price is NZ$383
includes taxes & fees
10 Nov - 11 Nov
Charming 1-bedroom apartment with AC, WiFi in welcoming Albany

cozy retreat with modern amenties

2.0 star property
Delmar
The price is NZ$551
includes taxes & fees
10 Nov - 11 Nov
cozy retreat with modern amenties

Charming Apt in 18th c Berkshire Farmhouse

Lanesborough
9.4 out of 10, Exceptional, (39)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is NZ$369
includes taxes & fees
10 Nov - 11 Nov
Charming Apt in 18th c Berkshire Farmhouse

Near Tanglewood: Historic Summer Retreat

New Lebanon
9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
United States
Patty W.
The price is NZ$656
includes taxes & fees
10 Nov - 11 Nov
Near Tanglewood: Historic Summer Retreat

Chic Madison Parkview

Albany
9.6 out of 10, Exceptional, (27)
"Good location and well kept"
United States
Steve J.
The price is NZ$311
includes taxes & fees
10 Nov - 11 Nov
Chic Madison Parkview

Berkshires Apartment at the Stephentown Hotel

Stephentown
10.0 out of 10, Exceptional, (3)
"Our stay exceeded our expectations! The property is beautiful with a cute patio and modern furnishings/appliances. It had a homey and clean vibe and Dillon was nice enough to provide snacks, oatmeal, coffee, creamer, toothbrushes, etc. Everything we could need! We brought our two dogs and they seemed right at home and love going on walks through the fall leaves. Would definitely recommend for those with dogs, small children, or just traveling on their own!"
United States
Anja H.
The price is NZ$404
includes taxes & fees
11 Nov - 12 Nov
Berkshires Apartment at the Stephentown Hotel

✨Historic Full Amenities 2BR Apt @ Downtown Albany

Pastures
9.0 out of 10, Wonderful, (18)
"Close to everything downtown. Great location when attending events at MVP arena. Off street designated parking is a very nice bonus for this location. Host was very easy to communicate with and very responsive."
United States
Andreus H.
The price is NZ$353
includes taxes & fees
10 Nov - 11 Nov
✨Historic Full Amenities 2BR Apt @ Downtown Albany

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

Hancock
10.0 out of 10, Exceptional, (4)
"This is my favorite unit of all the units I have stayed in! The pirate stuff was so cool and we could see our kids ski from the inside! The owner is so easy to communicate with. We love having the ability to cook and spread out while we are in the unit. We aaaaargh definitely going to stay here again!"
United States
Stephanie K.
The price is NZ$417
includes taxes & fees
12 Nov - 13 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Stylish loft in the heart of downtown Troy with onsite parking

Troy
10.0 out of 10, Exceptional, (7)
"Will stay again when I’m Troy"
United States
mark
The price is NZ$253
includes taxes & fees
16 Nov - 17 Nov
Stylish loft in the heart of downtown Troy with onsite parking

2 bed room Apartment

South End
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 NZ$317
includes taxes & fees
10 Nov - 11 Nov
2 bed room Apartment

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is NZ$429
includes taxes & fees
12 Nov - 13 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
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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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 favorite 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 depends 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 NZ$202 per night. Entering your travel dates in the search wizard you might find 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?

Amazing Estate! 1,500-2,500 OFF NOW w/ Early Booking on 2026 week-long vacation!: 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 5 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.