Spencertown Vacations from $627

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The Latest Spencertown vacation packages

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

Hotel Vienna

3 out of 5
Save 100% on your flight
Price was $822, price is now $627 per person
$627
per person
Sep 3 - Sep 7
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
9.4/10 Exceptional! (808 reviews)
The access to the Windam Path was great. It is a lovely, easy walk by a stream and through meadows.

Reviewed on Jun 19, 2026

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Save 100% on your flight
Price was $1,088, price is now $877 per person
$877
per person
Sep 3 - Sep 7
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
8.8/10 Excellent! (99 reviews)
Beautiful and spacious balcony overlooking the mountains and golf course. We loved the view from our room 521. . Great place to relax before dinner with a glass of wine/cheese. Location is good within walking distance to a most wonderful restaurant named prominence. Highly recommend. The on site restaurant was nice too. Biggest disadvantage was the tv as it does not have any cable and then ending up with no signal at all. Other than that it was a really great place to stay.

Reviewed on Jun 15, 2026

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,008, price is now $874 per person
$874
per person
Sep 4 - Sep 7
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Hudson (HCC)
7.6/10 Good! (29 reviews)
I stayed in the mirror cabin everything was great just prepare to have no microwave and or a burner. So you cannot cook or heat anything up. I was able to make it work by just getting stuff that can be eaten cold and then going out to dinner which was fine. Also because the cabin is mirror please note birds constantly fly into it on purpose. It was one bird that every day i was there from morning to night was hitting the glass and it did get very annoying.

Reviewed on Apr 20, 2026

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Spencertown Hotel Deals

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $139 total per night from Jun 24 to Jun 25
$139 total
Jun 24 - Jun 25
Total with taxes and fees
9.2/10 Wonderful! (1,003 reviews)
"Will definitely stay at this property again!"

Reviewed on Jun 20, 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $173 total per night from Jun 22 to Jun 23
$173 total
Jun 22 - Jun 23
Total with taxes and fees
9/10 Wonderful! (992 reviews)
"Good"

Reviewed on Jun 21, 2026

Berkshire Mountain Lodge
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Fully refundable
$104 nightly
The price is $116 total per night from Jun 24 to Jun 25
$116 total
Jun 24 - Jun 25
Total with taxes and fees
8.6/10 Excellent! (1,009 reviews)
"Good breakfast"

Reviewed on Jun 20, 2026

Quality Inn Great Barrington
See all 1,387 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

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Frequently asked questions

How much does a Spencertown vacation package cost?
You'll find cheap prices from $627 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.