East Chatham Holiday Rentals

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Our top choices for East Chatham holiday rentals

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
Luxury Barn Retreat — All-Season Escape Awaits!

Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.
Chatham
10.0 out of 10, Exceptional, (3 reviews)
"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 HK$1,447
HK$2,514 total
includes taxes & fees
2 Mar - 3 Mar
Sugar Shack - 300 square feet of pure sweetness.

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (9 reviews)
"Healthy food too!"
United States
GEORGINA
The price is HK$1,317
HK$1,471 total
includes taxes & fees
16 Mar - 17 Mar
Huttopia Berkshires

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

BLUSH: Boutique TINY home*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (7 reviews)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is HK$1,479
HK$2,515 total
includes taxes & fees
10 Mar - 11 Mar
BLUSH: Boutique TINY home*private spa*walk to town

Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods
Sand Lake
10.0 out of 10, Exceptional, (13 reviews)
"Loved this cabin! The communal building is very clean & bathrooms are spotless. There is a farm stand near the entrance where you can buy firewood and fresh eggs. Trails are literally connected to the property for easy nature walks. We plan on coming back!"
United States
Abby L.
The price is HK$978
HK$1,433 total
includes taxes & fees
2 Mar - 3 Mar
Taborton Harvest Boulder Pines Cabin in the woods

Pet-Friendly Hudson Escape w/ Hot Tub

Pet-Friendly Hudson Escape w/ Hot Tub
Stottville
The price is HK$1,252
HK$2,358 total
includes taxes & fees
2 Mar - 3 Mar
Pet-Friendly Hudson Escape w/ Hot Tub

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (29 reviews)
"Good for a quick overnight - host was very accommodating when we needed an early check-in."
United States
Katie B.
The price is HK$831
HK$1,106 total
includes taxes & fees
2 Mar - 3 Mar
All the comforts of home

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (137 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
The price is HK$1,017
HK$1,139 total
includes taxes & fees
2 Mar - 3 Mar
Micosta Leisure Inn

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

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is HK$821
HK$1,818 total
includes taxes & fees
2 Mar - 3 Mar
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (54 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$767
HK$1,035 total
includes taxes & fees
2 Mar - 3 Mar
All comforts of home

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is HK$1,408
HK$2,403 total
includes taxes & fees
2 Mar - 3 Mar
3-bedroom house in beautiful Berkshires, close to amenities!

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (27 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is HK$1,260
HK$2,107 total
includes taxes & fees
3 Mar - 4 Mar
Home in Great Barrington

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is HK$821
HK$1,818 total
includes taxes & fees
2 Mar - 3 Mar
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is HK$821
HK$1,818 total
includes taxes & fees
2 Mar - 3 Mar
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.0 out of 10, Good, (4 reviews)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is HK$1,244
HK$1,568 total
includes taxes & fees
2 Mar - 3 Mar
The Brooks Motel: Exceptional Suite

Treat yourself at the stunning June Farms Wellness Huts!

Treat yourself at the stunning June Farms Wellness Huts!
West Sand Lake
10.0 out of 10, Exceptional, (8 reviews)
"The wellness hut was an amazing getaway. Beautiful interior and design. Loved the little outdoor sauna. Loved the front porch/deck. Would definitely return for another stay."
United States
SteveS
The price is HK$1,943
HK$3,503 total
includes taxes & fees
2 Mar - 3 Mar
Treat yourself at the stunning June Farms Wellness Huts!

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale
9.8 out of 10, Exceptional, (36 reviews)
"Amazing, peaceful, immaculately clean property. "
United States
Cec C.
The price is HK$2,011
HK$4,195 total
includes taxes & fees
30 Mar - 31 Mar
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,273 reviews)
"Excellent location and terrific space and amenities."
United States
Michelle
The price is HK$813
HK$994 total
includes taxes & fees
31 Mar - 1 Apr
Vacation Village in the Berkshires

★SPACIOUS 1BR Apt w/ Character 10ft Ceilings W/D!★

★SPACIOUS 1BR Apt w/ Character 10ft Ceilings W/D!★
Mansion
9.8 out of 10, Exceptional, (6 reviews)
"A charming one bedroom near the cathedral and New York State museum. We enjoyed our stay!"
United States
Michael C.
The price is HK$838
HK$1,708 total
includes taxes & fees
6 Mar - 7 Mar
★SPACIOUS 1BR Apt w/ Character 10ft Ceilings W/D!★

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Nassau
10.0 out of 10, Exceptional, (2 reviews)
"Cozy home on the lake."
United States
Terry O.
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
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 East Chatham Hotel Reviews

Find out more about East Chatham

Search for holiday rentals in East Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in East Chatham using one of the methods below:

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Frequently asked questions

Can I find a holiday rental in East Chatham?

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

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

Pool & Secluded Historic Estate on the Hudson | River House by AvantStay: This holiday home rental outside of East Chatham is located on a river, and has an arcade/games room, a BBQ and air conditioning to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in East Chatham?

Expedia has 8 holiday rentals for your stay in East Chatham.

What can I see and do in East Chatham?

Meizinger Lake and Hand Hollow Conservation Area are a couple of lovely local spots to get outside and enjoy nature. Hand Hollow State Forest and Queechy Lake are a couple of places you'll find in the wider area.

What are holiday rentals like in East Chatham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in East Chatham. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family trip.