Cummington Vacations from $631

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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.
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Price was $894, price is now $631 per person
$631
per person
Dec 23 - Dec 30
found 1 hour ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
9.2/10 Wonderful! (2,088 reviews)
Well located hotel w good spa option...room w fireplace and kitchenette was especially nice touch!...adjoining restaurant pricey but nice treat...parking can be an issue

Reviewed on Nov 1, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was $2,094, price is now $921 per person
$921
per person
Dec 15 - Dec 22
found 21 hours ago
Roundtrip flight included
San Juan (SJU) 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 $1,961, price is now $1,136 per person
$1,136
per person
Jan 20 - Jan 24
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Price was $1,060, price is now $669 per person
$669
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
Overall stay was wonderful!

Reviewed on Nov 1, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Price was $2,178, price is now $1,452 per person
$1,452
per person
Jan 25 - Jan 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (491 reviews)

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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
$120 nightly
The price is $134 total per night from Dec 2 to Dec 3
$134 total
Dec 2 - Dec 3
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
$120 nightly
The price is $134 total per night from Dec 1 to Dec 2
$134 total
Dec 1 - Dec 2
Total with taxes and fees
9/10 Wonderful! (1,007 reviews)
"Lovely room, great location, staff excellent"

Reviewed on Nov 1, 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 $131 total per night from Nov 4 to Nov 5
$131 total
Nov 4 - Nov 5
Total with taxes and fees
9.2/10 Wonderful! (2,078 reviews)
"Well located hotel w good spa option...room w fireplace and kitchenette was especially nice touch!...adjoining restaurant pricey but nice treat...parking can be an issue"

Reviewed on Nov 1, 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 $631 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.