Spencertown Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

Photo by Charlie Rhodes

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 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

Top hotels in Spencertown

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is ฿4,043 per night from 27 Aug to 28 Aug
฿4,043
฿5,267 total
27 Aug - 28 Aug
includes taxes & fees
Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is ฿5,298 per night from 30 Jul to 31 Jul
฿5,298
฿5,917 total
30 Jul - 31 Jul
includes taxes & fees
9.2/10 Wonderful! (1,028 reviews)
"I would stay here again for sure. Nice clean room, generous breakfast, pool and hot tub, what’s not to like? Very convenient to Bousquet ski area. Restaurants nearby. Easy drive into either Lenox or Pittsfield."

Reviewed on 28 Jul 2026

The Yankee Inn
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
The price is ฿5,061 per night from 25 Aug to 26 Aug
฿5,061
฿5,654 total
25 Aug - 26 Aug
includes taxes & fees
9/10 Wonderful! (1,022 reviews)
"I enjoyed how homey the property was in the evenings. The fire pits, outdoor lighting, and music were all so welcoming."

Reviewed on 28 Jul 2026

Berkshires Untold
See all 1,397 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.