Chatham Vacation Rentals

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Check prices for these dates

In two weeks
Jan 23 - Jan 25
In two months
Mar 6 - Mar 8
In three months
Apr 3 - Apr 5
In four months
May 1 - May 3

Our top choices for Chatham vacation rentals

Dining
Sugar Shack - 300 square feet of pure sweetness.

Mobile Home in Chatham

Sugar Shack - 300 square feet of pure sweetness.
2.0 star property
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 ￥33,946
￥56,974 total
includes taxes & fees
Jan 12 - Jan 13
Sugar Shack - 300 square feet of pure sweetness.
Fridge, microwave, oven, stovetop
HunnyHAUS: Deluxe TINY*private spa*walk to town

Mobile Home in Chatham

HunnyHAUS: Deluxe TINY*private spa*walk to town
10.0 out of 10, Exceptional, (9 reviews)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is ￥35,525
￥65,164 total
includes taxes & fees
Jan 13 - Jan 14
HunnyHAUS: Deluxe TINY*private spa*walk to town
Terrace/patio
BLUSH: Boutique TINY home*private spa*walk to town

Mobile Home in Chatham

BLUSH: Boutique TINY home*private spa*walk to town
10.0 out of 10, Exceptional, (6 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 ￥33,946
￥56,974 total
includes taxes & fees
Jan 12 - Jan 13
BLUSH: Boutique TINY home*private spa*walk to town
Property grounds
Renovated house. Built in 1890s. No neighbors in sight.

Vacation Home in Chatham

Renovated house. Built in 1890s. No neighbors in sight.
2.0 star property
The price is ￥22,105
￥41,203 total
includes taxes & fees
Jan 25 - Jan 26
Renovated house. Built in 1890s. No neighbors in sight.
Exterior
Huttopia Berkshires

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7 reviews)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is ￥30,196
￥33,729 total
includes taxes & fees
Jan 13 - Jan 14
Huttopia Berkshires
View from property
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Cabin in Catskill

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
9.6 out of 10, Exceptional, (125 reviews)
"I loved every single part of the stay "
United States
Srijana
The price is ￥20,368
￥28,820 total
includes taxes & fees
Jan 14 - Jan 15
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby
Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,204 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is ￥16,416
￥20,068 total
includes taxes & fees
Jan 12 - Jan 13
Vacation Village in the Berkshires
Exterior
Micosta Leisure Inn

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.4 out of 10, Exceptional, (135 reviews)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
Micosta Leisure Inn
Interior
Charming loft cottage in tranquil Germantown with WiFi, AC

Cottage in Germantown

Charming loft cottage in tranquil Germantown with WiFi, AC
10.0 out of 10, Exceptional, (9 reviews)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
The price is ￥17,210
￥33,599 total
includes taxes & fees
Jan 12 - Jan 13
Charming loft cottage in tranquil Germantown with WiFi, AC
Outdoor dining
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cottage in Nassau

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (2 reviews)
"Cozy home on the lake."
United States
Terry O.
The price is ￥24,868
￥58,625 total
includes taxes & fees
Jan 12 - Jan 13
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (989 reviews)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ￥34,578
￥38,624 total
includes taxes & fees
Jan 12 - Jan 13
Jiminy Peak Mountain Resort
Pool
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is ￥21,631
￥43,562 total
includes taxes & fees
Jan 13 - Jan 14
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Fridge, microwave, oven, stovetop
Taborton Harvest Timber Trails Unique cabin experience

Cabin in Sand Lake

Taborton Harvest Timber Trails Unique cabin experience
10.0 out of 10, Exceptional, (1 review)
"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."
United States
Georgia M.
The price is ￥19,736
￥28,917 total
includes taxes & fees
Jan 12 - Jan 13
Taborton Harvest Timber Trails Unique cabin experience
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 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 ￥23,873
￥40,598 total
includes taxes & fees
Jan 25 - Jan 26
Home in Great Barrington
Property grounds
All comforts of home

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (52 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is ￥15,489
￥20,883 total
includes taxes & fees
Jan 12 - Jan 13
All comforts of home
Exterior
Near Tanglewood: Historic Summer Retreat

Vacation Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (24 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is ￥18,899
￥55,651 total
includes taxes & fees
Jan 20 - Jan 21
Near Tanglewood: Historic Summer Retreat
House (3 Bedrooms) | Interior
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
The price is ￥30,946
￥87,412 total
includes taxes & fees
Jan 13 - Jan 14
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Property grounds
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Apartment in Hancock

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (5 reviews)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is ￥21,631
￥43,385 total
includes taxes & fees
Jan 12 - Jan 13
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Property grounds
2 Bed Berkshire Getaway @ Stephentown Hotel

Apartment in Stephentown

2 Bed Berkshire Getaway @ Stephentown Hotel
10.0 out of 10, Exceptional, (5 reviews)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
The price is ￥27,875
￥51,094 total
includes taxes & fees
Jan 12 - Jan 13
2 Bed Berkshire Getaway @ Stephentown Hotel
Exterior
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Cabin in Catskill

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
9.8 out of 10, Exceptional, (35 reviews)
"Cozy and a great front porch to enjoy morning coffee and the evenings."
United States
Crystal B.
The price is ￥23,447
￥51,754 total
includes taxes & fees
Jan 15 - Jan 16
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill
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 Chatham Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"I loved every single part of the stay "
Srijana 1-night trip
Posted 3 days ago
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Find out more about Chatham

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

  • View our selection of featured holiday rentals in Chatham
  • Use the map to find apartments and other holiday homes in the Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

Frequently asked questions

Are there vacation rentals in Chatham?

Yes, we have vacation rentals close to top points of interest in Chatham, or you can go with a secluded option if you want a relaxing place to stay. Chatham is known for its theaters and restaurants.

What are some of the best vacation home rentals that Chatham has to offer?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This vacation home rental near Chatham offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Chatham?

With 13 Expedia vacation rentals, you're sure to find just the right place for your Chatham stay.

What can I see and do in Chatham?

While exploring the area, visit family-friendly sights like Bousquet Ski Area, or get outside and enjoy nature at Kinderhook Lake. The Mac-Haydn Theatre and Martin Van Buren National Historic Site are a couple of places you'll find in the larger area.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or more in Chatham. Vacation rentals feature amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family getaway.