Name: Vacation Village in the Berkshires
Price range: CA $157
Rating: 8.8

Your Chatham Vacation

The adventure-packed city of Chatham is calling. Delve into everything from its highlights to its hidden gems with a Chatham vacation package that's customized to you. Any trip to Chatham needs a well-planned itinerary. Fill yours with attractions like Martin Van Buren National Historic Site, Art Omi International Arts Center - Fields Sculpture Park and The Mac-Haydn Theatre. Browse Expedia's wide range of travel options and start organizing your ideal vacation to Chatham today.

Top Chatham Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Weathervane Motel

CA $1,069

per person

Aug 24 - Aug 28

found 9 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Albany (ALB)

6.8/10 (772 reviews)

EXTREMELY helpful manager! Great shower, great bathroom.

Reviewed on Jun 2, 2026

The White House Inn

CA $1,496

per person

Aug 24 - Aug 28

found 9 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Albany (ALB)

9.2/10 Wonderful! (317 reviews)

Beautiful, quiet and peaceful location. Gorgeous property

Reviewed on Jun 16, 2026

The Equinox Golf Resort & Spa

Manchester Village Historic District

CA $1,208

per person

Aug 24 - Aug 28

found 9 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Albany (ALB)

7.4/10 Good! (634 reviews)

Stayed as a bridesmaid and wedding guest in the hotel recently. The rooms were dated and we found mold on the shower ceiling tiles. The main building is kept in better condition but rooms could definitely use some TLC. Staff was super friendly though!

Reviewed on Jun 14, 2026

Four Winds Country Motel

CA $1,241

per person

Aug 24 - Aug 28

found 9 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Albany (ALB)

8.4/10 Very Good! (546 reviews)

We had a very enjoyable stay, and the breakfast had many items which appealed to us. We will stay at this hotel again.

Reviewed on Jun 8, 2026

Toll Road Inn

CA $1,235

per person

Aug 24 - Aug 28

found 9 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Albany (ALB)

9/10 Wonderful! (518 reviews)

Nice place, cute little brook out back, nice pool, close to town! A really great spot, will definitely be back.

Reviewed on Jun 15, 2026

Ready to book your vacation to Chatham?

Choose your dates

Chatham Hotel Deals

Country Inn & Suites by Radisson, Downtown Albany New York

300 Broadway Albany NY

Fully refundable

CA $159

CA $182 total

Jul 12 - Jul 13

includes taxes & fees

8/10 Very Good! (713 reviews)

"Clean room, very comfortable bed. Breakfast was a bit of a disappointment as stuff was either stale or overcooked. Resorted to toasted bagels, which was fine! Useful location for getting on/off the motorway. Also decent for walking into town to bars/pubs etc."

Reviewed on Jun 17, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

CA $171

CA $223 total

Jun 25 - Jun 26

includes taxes & fees

9/10 Wonderful! (987 reviews)

"The value for the price was outstanding! This place is really nice. \"

Reviewed on Jun 17, 2026

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

Fully refundableReserve now, pay when you stay

CA $157

CA $191 total

Jun 25 - Jun 26

includes taxes & fees

8.8/10 Excellent! (2,398 reviews)

"Nice staff and property but they don’t seem to see the Hotels.com notes so room was different and there was no upgrade."

Reviewed on Jun 17, 2026

See all 1,617 properties in Chatham

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.