Spencertown Holidays

Photo by Charlie Rhodes

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Spencertown

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street, South Lee, MA
The price is S$202 per night from 6 Aug to 7 Aug
S$202
6 Aug - 7 Aug
includes taxes & fees
9/10 Wonderful! (681 reviews)
"I liked the size of the rooms and how comfortable everything in the room was. It was stocked with everything we needed. I did not like the lack of accessibility for people with disabilities. There are elevators, but they are blocked, and there is limited disability parking. I was on the third floor ..."

Reviewed on 24 Jul, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
The price is S$186 per night from 17 Aug to 18 Aug
S$186
17 Aug - 18 Aug
includes taxes & fees
7.8/10 Good! (837 reviews)
"Convenient for our trip"

Reviewed on 27 Jul, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is S$257 per night from 24 Aug to 25 Aug
S$257
24 Aug - 25 Aug
includes taxes & fees
9/10 Wonderful! (649 reviews)
"It's a clean, nice place. And easy to get to the surrounding towns."

Reviewed on 28 Jul, 2025

Berkshires Untold
See all 1,339 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.

Frequently asked questions

How much does a Spencertown holiday package cost?
You'll find cheap prices 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 holiday to Spencertown costs.
What are the cheapest months to go to Spencertown?
To score cheap Spencertown holiday packages, plan your trip outside of peak periods such as public holidays. You'll generally find better availability and lower prices when it's less busy.
How many days is enough for Spencertown?
With a well-planned itinerary, you can easily tick off the top Spencertown sights in a few days. But if you prefer to discover hidden spots or go on day tours, think about booking your Spencertown holiday for longer.
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 holiday package as soon as possible.
Is it cheaper to book a Spencertown holiday as a package?
You can enjoy significant savings on your next Spencertown getaway by booking a customised holiday 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 holiday package to Spencertown?
If you're considering a spontaneous Spencertown holiday, 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.
How to plan a trip to Spencertown?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to travel to Spencertown.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and meals to activities and flights. Your hotel will probably be the largest expense during your trip to Spencertown.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Spencertown. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a tailored Spencertown holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.