Cummington Vacations from $620

Book a Hotel + Flight or Car together to unlock savings

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

$620

per person

Nov 9 - Nov 12

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

8.4/10 Very Good! (190 reviews)

The apt was tidy. Enough to sleep 8. Bathrooms were clean and updated. Parking can be difficult to find. It's about an hour from Salem.

Reviewed on Oct 4, 2026

Raffles Boston

Back Bay

Save 100% on your flight

$1,210

per person

Dec 16 - Dec 20

found 1 hour ago

Roundtrip non-stop flight included

Atlanta (ATL) to Boston (BOS)

9.6/10 Exceptional! (332 reviews)

The Langham, Boston

Downtown Boston

Save 100% on your flight

$770

per person

Dec 29 - Jan 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.8/10 Exceptional! (1,005 reviews)

The staff were incredibly helpful & nice. The hotel was beautiful & great location

Reviewed on Oct 4, 2026

Boston Harbor Hotel

North End

Save 100% on your flight

$1,077

per person

Dec 29 - Jan 1

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.8/10 Exceptional! (1,008 reviews)

Great location. A bit pricey for the size room. Easy to get most places by walking .

Reviewed on Oct 4, 2026

The Atlas Hotel Boston Cambridge

Allston

Save 100% on your flight

$756

per person

Nov 12 - Nov 15

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Boston (BOS)

9.4/10 Exceptional! (385 reviews)

Clean , very nice staff. Pricy for sure

Reviewed on Oct 5, 2026

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Cummington Hotel Deals

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$110 nightly

$123 total

Nov 1 - Nov 2

Total with taxes and fees

8.8/10 Excellent! (2,706 reviews)

"Great place to stay with a family but some of the furniture is showing wear and when we got into our room there was a paint can and a paint tarp in our bathroom. An oops by the hotel."

Reviewed on Oct 5, 2026

Hotel UMass

1 Campus Center Way Amherst MA

$144 nightly

$161 total

Oct 25 - Oct 26

Total with taxes and fees

9/10 Wonderful! (1,012 reviews)

"There was quite a line at the breakfast so I didn’t have time to make a waffle."

Reviewed on Oct 5, 2026

Berkshire Mountain Lodge

8 Dan Fox Dr Pittsfield MA

$115 nightly

$128 total

Nov 4 - Nov 5

Total with taxes and fees

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 $620 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.