Cummington Vacations from $761

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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

$761

per person

Dec 3 - Dec 7

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Boston (BOS)

8.4/10 Very Good! (190 reviews)

The accommodation was great and spacious enough for a large group. There were five of us, and it was perfect for our needs. The apartment was clean, and everything we needed was provided, including towels, soap, dishwasher detergent, and more. We turned on the oven to make dinner, but we were unable to turn it off because the buttons weren’t working. We called for assistance and received a response very quickly, which made us feel supported and taken care of. Overall, we had a great stay! The apartment was lovely, and the location was excellent, especially for getting to Boston by public transportation.

Reviewed on Oct 17, 2026

Raffles Boston

Back Bay

Save 100% on your flight

$1,714

per person

Dec 5 - Dec 11

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Boston (BOS)

9.6/10 Exceptional! (332 reviews)

A stunning hotel with super helpful staff. Would highly recommend the Raffles, from start to finish it was excellent and we’ll definitely be back.

Reviewed on Oct 14, 2026

Boston Harbor Hotel

North End

Save 100% on your flight

$1,116

per person

Dec 26 - Dec 29

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

9.8/10 Exceptional! (1,008 reviews)

Amazing staff and property

Reviewed on Oct 18, 2026

Four Seasons Hotel Boston

Bay Village

Save 100% on your flight

$1,390

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Boston (BOS)

9.4/10 Exceptional! (487 reviews)

Your staff is Five star! Hotel needs updating badly. My far the worst Four Seasons we have stayed in. On the day of check-in, our flight was delayed and we got in at 2:30 in the morning had room service and it was an edible. Your staff indicated they would remove the charges, but I see we were still charged for them as well.

Reviewed on Oct 6, 2026

Battery Wharf Hotel, Boston Waterfront

North End

$804

per person

Dec 4 - Dec 7

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Boston (BOS)

9/10 Wonderful! (2,041 reviews)

Loved it!

Reviewed on Oct 19, 2026

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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

$126 nightly

$140 total

Nov 18 - Nov 19

Total with taxes and fees

8.8/10 Excellent! (2,763 reviews)

"⭐⭐⭐⭐☆ (4/5 Stars) My group and I recently stayed at Vacation Village in the Berkshires. The property is beautiful, well maintained, and located in a lovely area. We especially enjoyed the pool and jacuzzi, which were excellent amenities and a highlight of our stay. Unfortunately, I cannot give a ..."

Reviewed on Oct 19, 2026

Hotel UMass

1 Campus Center Way Amherst MA

9/10 Wonderful! (1,009 reviews)

"There is no protein option for breakfast. Milk might be the only choice. I personally don’t like to have carbs and anything sweet in the morning. If you are from Asia, American style breakfast might be a concern. Other than that, overall I enjoy my stay here. Perfect location to enjoy the foliage ..."

Reviewed on Oct 18, 2026

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D. Hotel Suites & Spa

1 Country Club Rd Holyoke MA

Fully refundable

$125 nightly

$139 total

Oct 29 - Oct 30

Total with taxes and fees

9.2/10 Wonderful! (2,086 reviews)

"Facilities were good. The rooms are dated"

Reviewed on Oct 18, 2026

See all 896 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 $761 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.