Cummington Vacations from $496

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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

Boston Lodge and Suites

4 out of 5
Dorchester
Save 100% on your flight
Price was $1,016, price is now $496 per person
$496
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Austin (AUS) to Boston (BOS)
8.4/10 Very Good! (194 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

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,757, price is now $1,072 per person
$1,072
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Austin (AUS) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $1,149, price is now $784 per person
$784
per person
Jan 15 - Jan 18
found 4 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Hartford (BDL)
9.8/10 Exceptional! (1,003 reviews)
best overnight stay ever, loved every thing about this property

Reviewed on Nov 5, 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was $1,733, price is now $1,199 per person
$1,199
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Austin (AUS) to Boston (BOS)
9.4/10 Exceptional! (744 reviews)
Beautiful hotel and the staff was wonderful. They gave us a corner room with a great view of the city. The room was spacious with a comfortable seating area.

Reviewed on Nov 7, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was $1,828, price is now $1,272 per person
$1,272
per person
Dec 23 - Dec 26
found 1 day ago
Roundtrip flight included
Austin (AUS) to Boston (BOS)
9.4/10 Exceptional! (465 reviews)
Overall Excellent! clean room, very nice staff

Reviewed on Nov 4, 2026

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Cummington Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $136 total per night from Dec 8 to Dec 9
$136 total
Dec 8 - Dec 9
Total with taxes and fees
Vacation Village in the Berkshires
Hotel UMass

Hotel UMass

2.5 out of 5
1 Campus Center Way Amherst MA
Fully refundable
$97 nightly
The price is $108 total per night from Dec 3 to Dec 4
$108 total
Dec 3 - Dec 4
Total with taxes and fees
9/10 Wonderful! (1,003 reviews)
"The room was lovely, modern and very clean and the parking is conveniently located. Basic continental breakfast just adequate to get the day started. Student dining hall is definitely the best option if you want a full hot more complete meal but overall the stay at Hotel UMass was great."

Reviewed on Nov 7, 2026

Hotel UMass
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundable
$118 nightly
The price is $132 total per night from Dec 9 to Dec 10
$132 total
Dec 9 - Dec 10
Total with taxes and fees
9.2/10 Wonderful! (2,090 reviews)
"very comfortable, would stay again"

Reviewed on Nov 6, 2026

D. Hotel Suites & Spa
See all 885 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 $496 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.