Spencertown Vacations from $443

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The Latest Spencertown vacation packages

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

AutoCamp Catskills

5 out of 5
Price was $615, price is now $443 per person
$443
per person
Jan 16 - Jan 19
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
9/10 Wonderful! (423 reviews)
Clean room & pet friendly hotel

Reviewed on Nov 6, 2025

Deer Mountain Inn

Deer Mountain Inn

2 out of 5
Save 100% on your flight
Price was $1,025, price is now $771 per person
$771
per person
Jan 16 - Jan 19
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
9/10 Wonderful! (4 reviews)
I loved the guest room with the pool table and self attend bar.

Reviewed on Oct 22, 2024

Woodstock Way Hotel

Woodstock Way Hotel

4 out of 5
Save 100% on your flight
Price was $937, price is now $706 per person
$706
per person
Jan 16 - Jan 19
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
9.6/10 Exceptional! (193 reviews)
Room was great, highly recommend staying here!

Reviewed on Nov 3, 2025

Hotel Vienna

Hotel Vienna

2.5 out of 5
Price was $810, price is now $627 per person
$627
per person
Jan 16 - Jan 19
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
9.4/10 Exceptional! (663 reviews)
Room was nice and clean. The staff was beyond friendly and made me feel comfortable and welcomed. Would definitely stay here again!

Reviewed on Nov 8, 2025

Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
Save 100% on your flight
Price was $919, price is now $714 per person
$714
per person
Jan 16 - Jan 19
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Hudson (HCC)
8.8/10 Excellent! (74 reviews)
Really nice restored resort. Rooms were great, staff was friendly. The food is very good.

Reviewed on Nov 3, 2025

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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
$113 nightly
The price is $126 total per night from Nov 10 to Nov 11
$126 total
Nov 10 - Nov 11
Total with taxes and fees
9/10 Wonderful! (745 reviews)
Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you

Reviewed on Nov 2, 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
$98 nightly
The price is $109 total per night from Nov 21 to Nov 22
$109 total
Nov 21 - Nov 22
Total with taxes and fees
7.8/10 Good! (946 reviews)
Great stay! Nice quiet room for 2 little “alert “ to outside noise pups!! Comfy beds and central location for the day trips we had planned.

Reviewed on Nov 8, 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
$93 nightly
The price is $104 total per night from Nov 17 to Nov 18
$104 total
Nov 17 - Nov 18
Total with taxes and fees
9/10 Wonderful! (791 reviews)
Everything was clean and the staff were nice. However? I was told at check-in that rooms weren’t cleaned unless I requested it so I requested it for my 3 night stay but the room was only cleaned once.

Reviewed on Nov 4, 2025

Berkshires Untold
See all 1,348 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 $443 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.