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.
Hotel Vienna

Hotel Vienna

2.5 out of 5
Price was $408, price is now $357 per person
$357
per person
Dec 5 - Dec 7
found 22 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
9.4/10 Exceptional! (663 reviews)
Close to downtown, quiet, great staff

Reviewed on Oct 25, 2025

Eastwind Windham

Eastwind Windham

2 out of 5
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

Wylder Hotel Windham

3.5 out of 5
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

The Haüs Windham

2 out of 5
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 trips

Spencertown Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
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

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshires Untold

Berkshires Untold

3.5 out of 5
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

Berkshires Untold
See all 1,326 properties in Spencertown
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

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Spencertown vacation package cost?
You'll find cheap prices from $357 on Expedia for your Spencertown getaway. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Spencertown costs.
What are the cheapest months to go to Spencertown?
If you're looking to score a cheap Spencertown vacation package, consider traveling in June, September and October. You're likely to find better rates on hotels and airfares during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Spencertown?
Usually, a handful of days is enough to see the top sights during your Spencertown vacation. But if you want to have some time to chill out or take day trips, consider extending your itinerary.
How to find the best Spencertown package deals?
Use Expedia's filter tool to help you find some tempting Spencertown package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Spencertown package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Spencertown vacation as a package?
You can enjoy significant savings on your next Spencertown getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Spencertown?
If you're considering a spontaneous Spencertown vacation, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find awesome deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Spencertown vacation packages?
Set off on your perfect escape to Spencertown with help from Expedia's Book Now, Pay Later vacations. There's no need to save like crazy or wait until your next paycheck — we've partnered with online lender Affirm to give you more financial flexibility. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stay on budget and snap up cheap deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.