
Spencertown Vacations from $357
Book a Hotel + Flight or Car together to unlock savings
Photo by Charlie Rhodes
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Spencertown vacation packages
Price found within the past 48 hours. Click for updated prices.


Eastwind Windham
Price was $496, price is now $427 per person
$427
per person
Dec 5 - Dec 7
found 22 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
9.2/10 Wonderful! (62 reviews)
Not sure how there were "exceptional" ratings prior to our visit. We were in main building which is on a major road and noisy but they did provide ear plugs. Some mold in corner of shower and they must have well water because it had a sulphur odor. Parking was fine. Would not return.
Reviewed on Oct 14, 2025

Wylder Hotel Windham
Price was $490, price is now $427 per person
$427
per person
Dec 5 - Dec 7
found 22 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
8.8/10 Excellent! (74 reviews)
The property was very nice. The staff was very friendly and accommodating. Overall our stay was great. My only complaint would be the inconvenience about morning coffee. There is no coffee pot in the rooms and no coffee in the lobby. You have to walk to another building to a bakery to purchase coffee and they don’t open until 7:00. My husband is an early riser and likes his coffee
Reviewed on Oct 13, 2025

The Haüs Windham
Price was $643, price is now $567 per person
$567
per person
Dec 5 - Dec 7
found 22 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
8.6/10 Excellent! (15 reviews)
Hot tub could have been cleaner but all in all. Beautiful and amazing views! Great service with the front desk calls and extra towels provided no problem!
Reviewed on Sep 15, 2025
Don't see what you're looking for?
See all available trips from Columbus to Spencertown
View all tripsSpencertown Hotel Deals

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $108 total per night from Nov 2 to Nov 3
$108 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (723 reviews)
We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful..
Reviewed on Oct 22, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Fully refundable
$103 nightly
The price is $115 total per night from Nov 2 to Nov 3
$115 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (917 reviews)
All was very good at this hotel, our room was modernized and updated. The people at the front desk as well as all the employees were all well trained and pleasant . Pittsfield is in the middle of The Berkshires and so it was a great location to see what we wanted to see.
Reviewed on Oct 22, 2025

Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $105 total per night from Nov 2 to Nov 3
$105 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (776 reviews)
Had a lovely stay at the Berkshires Untold! We checked in late and the staff reached out to confirm our arrival time and accommodated us without issue. The lobby was absolutely gorgeous and this renovated motel was very well done. We didn’t get to enjoy the fire pits outside but they looked cozy. ...
Reviewed on Oct 23, 2025
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.
Find the Best Spencertown Vacation Packages
Spencertown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | The Mac-Haydn Theatre, Shaker Museum and Library and Hudson Chatham Winery |
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















