Old Chatham Vacation Rentals

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Vacation Rentals in Old Chatham

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

9.6 out of 10, Exceptional, (88)
"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, (1967)
"Beautiful location!"
The price is CA $147
CA $180 total
includes taxes & fees
Sep 11 - Sep 12
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (967)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is CA $220
CA $246 total
includes taxes & fees
Sep 1 - Sep 2
Jiminy Peak Mountain Resort

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (117)
"Great stay!"
The price is CA $180
CA $201 total
includes taxes & fees
Sep 1 - Sep 2
Micosta Leisure Inn

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect place for a relaxing getaway! We loved everything! "
The price is CA $135
CA $151 total
includes taxes & fees
Sep 1 - Sep 2
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 CA $180
CA $262 total
includes taxes & fees
Aug 25 - Aug 26
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 CA $301
CA $429 total
includes taxes & fees
Aug 24 - Aug 25
cozy retreat with modern amenties

Spacious 5-bedroom house in charming Lee with WiFi

The price is CA $588
CA $1,103 total
includes taxes & fees
Sep 2 - Sep 3
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 CA $149
CA $221 total
includes taxes & fees
Aug 25 - Aug 26
The Rizzy Apartment

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is CA $758
CA $1,447 total
includes taxes & fees
Aug 25 - Aug 26
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 CA $180
CA $261 total
includes taxes & fees
Aug 25 - Aug 26
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 CA $223
CA $670 total
includes taxes & fees
Aug 26 - Aug 27
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 CA $137
CA $257 total
includes taxes & fees
Sep 11 - Sep 12
Chic Madison Parkview

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

★ 2 BEDROOM / 1 BATH TRENDY Apt ★ Downtown Albany

8.8 out of 10, Excellent, (28)
"Great place to stay for our quick trip to Albany for a graduation. Nice clean accommodations and the bed was comfortable which is always a plus!"
The price is CA $174
CA $339 total
includes taxes & fees
Aug 24 - Aug 25
★ 2 BEDROOM / 1 BATH TRENDY Apt ★ Downtown Albany
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

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?

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS: 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 5 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.