Spencertown Holidays

Photo by Charlie Rhodes

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Top hotels in Spencertown

The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is S$230 per night from 6 Jul to 7 Jul
S$230
6 Jul - 7 Jul
includes taxes & fees
9.2/10 Wonderful! (1,011 reviews)
"The friendly atmosphere coming from the staff."

Reviewed on 30 Jun, 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
The price is S$238 per night from 9 Jul to 10 Jul
S$238
9 Jul - 10 Jul
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Rooms were clean, parking easy, staff very helpful"

Reviewed on 1 Jul, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is S$270 per night from 15 Jul to 16 Jul
S$270
15 Jul - 16 Jul
includes taxes & fees
9/10 Wonderful! (994 reviews)
"I usually stay here and yes staff are nice and rooms are decent but I’ve seen a decline in amenities. Maybe the expense of things - bathrobe in room, water and snacks were what I was used to seeing .in the room."

Reviewed on 25 Jun, 2026

Berkshires Untold
See all 1,400 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.

Explore a world of travel with Expedia

* 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.