Cummington Vacations from $495
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Your Cummington Vacation
Take the stress out of planning your next epic adventure with a Cummington vacation package. Whether you're visiting for its food, history, art or other highlights, there's a never-ending supply of new experiences to be had. If seeing the sights is a priority during your trip to Cummington, make sure you stop by leading attractions like Chesterfield Gorge and Swift River. Browse Expedia's wide range of travel options and start organizing your dream vacation to Cummington now.
The Latest Cummington vacation packages
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
$495
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
The Mansion at Ocean Edge
$847
per person
Nov 11 - Nov 14
found 7 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.2/10 Very Good! (1,002 reviews)
Kyung and his team delivered on a special weekend get away for my wife’s 40th birthday! This is now our next favorite place on the cape and we look forward to many more memories being made @ Ocean Edge!
Thank you all!
The Contino’s
Reviewed on Sep 6, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
$867
per person
Nov 15 - Nov 18
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (265 reviews)
I had a King room with a fireplace, it was a nice size room and very clean. The bathroom was nice and they had a robe hanging for me. Little touches like personalized notes and soft drinks in the refrigerator and snacks to pick up for the room. The staff was very friendly. I'm not a breakfast eater so can't really comment on that although there was a nice continental spread and you could order off the menu. I will say that I was a bit disappointed in the restaurant. Had dinner there the night before and for the price, I felt the food was a little lackluster. The bartender was very nice and he was my server as well. All in all I really enjoyed my stay and if I go back to Lexington I would stay there again.
Reviewed on Sep 4, 2026
Cummington Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$122 nightly
$136 total
Sep 13 - Sep 14
Total with taxes and fees
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
$144 nightly
$160 total
Sep 20 - Sep 21
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Overall, clean property and the location is good"
Reviewed on Sep 9, 2026
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundable
$113 nightly
$126 total
Oct 1 - Oct 2
Total with taxes and fees
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 Cummington Vacation Packages
Cummington Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,000 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Glendale Falls, Skyline Trail and Petticoat Hill |
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Frequently asked questions
How much does a Cummington vacation package cost?
You'll find cheap prices from $495 on Expedia for your Cummington escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Cummington costs.
What are the cheapest months to go to Cummington?
You're likely to find lower rates and better availability in January, October and December. Browse our cheap Cummington vacation packages and you could score some great off-season deals.
How many days is enough for Cummington?
Generally, a handful of days is enough to see the top attractions during your Cummington vacation. But if you prefer to have time to chill out or take day trips, consider extending your itinerary.
How to find the best Cummington package deals?
Finding a cheap Cummington package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Cummington package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Cummington vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Cummington vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Cummington?
Score incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Cummington getaway.
Does Expedia offer Book Now, Pay Later Cummington vacation packages?
Set off on your ideal getaway to Cummington with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snap up travel deals before they disappear.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
