Search Villas in Chatham

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr
No exact matches found, but these alternatives could be just right

Recommended hotels in Chatham

Property grounds
Sugar Shack - 300 square feet of pure sweetness.

Sugar Shack - 300 square feet of pure sweetness.

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 HK$1,671
HK$2,805 total
includes taxes & fees
12 Jan - 13 Jan 2026
Sugar Shack - 300 square feet of pure sweetness.
Exterior
HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town

HunnyHAUS: Deluxe TINY*private spa*walk to town
Chatham
10.0 out of 10, Exceptional, (9)
"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 HK$1,751
HK$3,211 total
includes taxes & fees
13 Jan - 14 Jan 2026
HunnyHAUS: Deluxe TINY*private spa*walk to town
Exterior
BLUSH: Boutique TINY home*private spa*walk to town

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, (6)
"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$1,556
HK$2,659 total
includes taxes & fees
6 Jan - 7 Jan 2026
BLUSH: Boutique TINY home*private spa*walk to town
Exterior
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1002)
"Very friendly and good Breakfast."
United States
Jesse
The price is HK$589
HK$658 total
includes taxes & fees
2 Jan - 3 Jan 2026
Best Western Plus Berkshire Hills Inn & Suites
Exterior
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very good, (1000)
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is HK$686
HK$766 total
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
"Rooms were very clean and spacious."
United States
Morgan
The price is HK$1,049
HK$1,172 total
includes taxes & fees
6 Jan - 7 Jan 2026
Element Lenox Berkshires
Exterior
Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG
2.5 star property
West Coxsackie
8.4 out of 10, Very good, (985)
"Perfect spot for an overnight stay when coming to the area"
United States
Lisa
The price is HK$645
HK$697 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
View from property
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (117)
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
The price is HK$852
HK$1,256 total
includes taxes & fees
15 Jan - 16 Jan 2026
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is HK$786
HK$878 total
includes taxes & fees
7 Jan - 8 Jan 2026
The Yankee, Trademark Collection by Wyndham
Front of property
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
2.0 star property
Hudson
8.0 out of 10, Very good, (12)
"lovely place!"
United States
Samyuktha
The price is HK$1,516
HK$2,065 total
includes taxes & fees
20 Jan - 21 Jan 2026
Pocketbook Hotel and Bath
Exterior
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1000)
"My go to place for my ski weekends"
United States
Ryan
The price is HK$588
HK$657 total
includes taxes & fees
13 Jan - 14 Jan 2026
Quality Inn Great Barrington
Exterior
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (811)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
Monument Mountain Motel
View from property
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is HK$1,882
HK$2,363 total
includes taxes & fees
7 Jan - 8 Jan 2026
Prospect Berkshires
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (439)
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is HK$835
HK$917 total
includes taxes & fees
6 Jan - 7 Jan 2026
Shaker Mill Inn
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1001)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is HK$807
HK$902 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (799)
"Spacious room and loved pool and hot tub!"
United States
Deanna
The price is HK$767
HK$1,031 total
includes taxes & fees
11 Jan - 12 Jan 2026
Berkshire Mountain Lodge
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (714)
"We stay here every year and it never disappoints "
United States
Elizabeth
The price is HK$762
HK$851 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1001)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is HK$404
HK$443 total
includes taxes & fees
5 Jan - 6 Jan 2026
Pleasant Valley Motel West Stockbridge
Exterior
Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1001)
"Very comfortable beds! "
United States
Gerald
The price is HK$864
HK$966 total
includes taxes & fees
25 Jan - 26 Jan 2026
Hampton Inn & Suites Berkshires-Lenox
Exterior
The Red Lion Inn

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1003)
"Old time charm and hot tub under the stars"
United States
Lori
The price is HK$1,082
HK$1,556 total
includes taxes & fees
20 Jan - 21 Jan 2026
The Red Lion Inn
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chatham Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great place to stay!! Very clean and very professional team"
Maricel 3-night trip
Posted 2 days ago
Vacation Village in the Berkshires

Find out more about Chatham

Chatham Villas information

Number of reviews
11,891
Accommodation
3 Villas
Lowest Price
HK$443
Highest Price
HK$3,211

Frequently asked questions

Why book your villa in Chatham with Expedia?
Booking a villa in Chatham is as simple as entering your travel dates and selecting a place that suits your style. Seeking something budget friendly or upmarket, or a property that also features a kitchen? Use Expedia's search filters to narrow your results and find your ideal pad.
How can I find cheap villas in Chatham?
Expedia can help you search for cheap villas in Chatham. Use our handy filter tool to choose budget, star rating and amenities to refine your search and find the perfect stay in a few quick keystrokes.
What is there to do near my villa in Chatham?
If you're ready to see the sights of Chatham, pay a visit to The Mac-Haydn Theatre. It's a favourite with tourists and locals alike.

Explore a world of travel with Expedia