Cummington Vacations from $735

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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 Harbor Hotel

North End

Save 100% on your flight

$735

per person

Dec 5 - Dec 7

found 1 day ago

Roundtrip non-stop flight included

Burbank (BUR) to Boston (BOS)

9.8/10 Exceptional! (1,005 reviews)

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

$1,323

per person

Nov 6 - Nov 9

found 18 hours ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

9.4/10 Exceptional! (484 reviews)

Room was very noisy in the morning and I could not sleep. Work is being done in the building and I was not informed of when arriving from west coast to stay for one night. Staff was very friendly and apologetic.

Reviewed on Sep 25, 2026

Luxury Apartments by Hyatus at Boston Everett

Save 100% on your flight

$10,096

per person

Nov 27 - Dec 1

found 12 hours ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

9.2/10 Wonderful! (9 reviews)

The Groton Inn

$790

per person

Nov 27 - Dec 1

found 12 hours ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

9.6/10 Exceptional! (547 reviews)

Raffles Boston

Back Bay

Save 100% on your flight

$1,359

per person

Nov 23 - Nov 27

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Boston (BOS)

9.6/10 Exceptional! (329 reviews)

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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 28 - Sep 29

Total with taxes and fees

8.8/10 Excellent! (2,678 reviews)

"It was a well appointed suite with kitchen, dining area, living room with a fireplace and the bedroom and a nice quiet corner of the property. I did sit out on the balcony and watch the sun go down and I had the best night sleep. I’ve had in a long time I would definitely go back. I didn’t use any ..."

Reviewed on Sep 26, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

Fully refundableReserve now, pay when you stay

$109 nightly

$121 total

Oct 1 - Oct 2

Total with taxes and fees

D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Fully refundable

$142 nightly

$158 total

Sep 28 - Sep 29

Total with taxes and fees

9.2/10 Wonderful! (2,097 reviews)

"If you choose to stay here, know that you need to eat in town or bring your own food! Restaurant food was cold and just not tasteful at all. And to make matters worse, breakfast was awful. Don't eat anything at the restaurant or breakfast..."

Reviewed on Sep 27, 2026

See all 894 properties in Cummington

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 $735 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.

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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.