Holiday Rentals in Old Chatham

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Holiday Rentals in Old Chatham

Our top choices for Old Chatham holiday rentals

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

9.6 out of 10, Exceptional, (90)
"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, (1974)
"Beautiful location!"
The price is €112
includes taxes & fees
7 Sept - 8 Sept
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (969)
"Quiet, clean, accessible. "
The price is €153
includes taxes & fees
2 Sept - 3 Sept
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (117)
"Great stay!"
The price is €125
includes taxes & fees
10 Sept - 11 Sept
Micosta Leisure Inn

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 €94
includes taxes & fees
2 Sept - 3 Sept
Huttopia Berkshires

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (126)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
The Ponds at Foxhollow

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 €168
includes taxes & fees
29 Aug - 30 Aug
Taborton Harvest Boulder Pines Cabin in the woods

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

cozy retreat with modern amenties

2.0 star property
The price is €266
includes taxes & fees
28 Aug - 29 Aug
cozy retreat with modern amenties

Spacious 5-bedroom house in charming Lee with WiFi

The price is €703
includes taxes & fees
3 Sept - 4 Sept
Spacious 5-bedroom house in charming Lee with WiFi

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (28)
"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

The Rizzy Apartment

7.2 out of 10, Good, (7)
"Great time "
The price is €190
includes taxes & fees
8 Sept - 9 Sept
The Rizzy Apartment

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is €980
includes taxes & fees
22 Sept - 23 Sept
Hancock Village Inn at Jiminy Peak

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 €166
includes taxes & fees
29 Aug - 30 Aug
Taborton Harvest Timber Trails Unique cabin experience

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

9.8 out of 10, Exceptional, (146)
"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

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is €431
includes taxes & fees
28 Aug - 29 Aug
Comfortable Berkshires retreat on mtn resort, SISO

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

10.0 out of 10, Exceptional, (166)
"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

Chic Madison Parkview

9.6 out of 10, Exceptional, (25)
"the apartment was in a great location, easy check-in, very simple check-in"
The price is €164
includes taxes & fees
21 Sept - 22 Sept
Chic Madison Parkview

Rose Cottage

9.6 out of 10, Exceptional, (5)
"It's so peaceful there. It was lovely."
Rose Cottage

River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool

9.4 out of 10, Exceptional, (16)
"The house is so historic and very beautiful/interesting. We had a great time. "
River House by AvantStay | Historic & Secluded Estate on the Hudson River w/Pool
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, apart-hotels, 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 €94 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?

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 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.