Cummington Vacations from $411

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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.
Inn at Middletown

Inn at Middletown

3.5 out of 5
Washington Street Historic District
Save 100% on your flight
Price was $661, price is now $411 per person
$411
per person
Jan 8 - Jan 11
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Hartford (BDL)
9/10 Wonderful! (526 reviews)
Great Inn, walkable area surrounding the property with nice views. Parking isn’t great and there wasn’t a valet available. Room was cozy and comfortable and dining at the inn was convenient and upscale.

Reviewed on Nov 15, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,400, price is now $764 per person
$764
per person
Feb 14 - Feb 18
just found
Roundtrip flight included
Los Angeles (LAX) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Clean room, staff is nice and helpful

Reviewed on Nov 29, 2025

Iris Hotel Boston

Iris Hotel Boston

4 out of 5
Coolidge Corner South Side
Save 100% on your flight
Price was $1,189, price is now $667 per person
$667
per person
Feb 12 - Feb 17
found 1 day ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
9.4/10 Exceptional! (460 reviews)
The entire experience at The Iris hotel was excellent form the Valet parking, the room, the bar & the restaurant. I would stay there anytime I'm in Brookline

Reviewed on Nov 22, 2025

Premier Suites - Bay Village

Premier Suites - Bay Village

2 out of 5
Bay Village
Save 100% on your flight
Price was $743, price is now $461 per person
$461
per person
Feb 3 - Feb 10
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Boston (BOS)
6.2/10 (245 reviews)
Great central location, but very over priced for what you get. Felt like I was going to fall through the floor. Super old building and nothing works that well. Internet on tv didn't work. Bath plug/stopper didn't work. Electric hotplate didn't work. Don't bring a large suitcase as the stairs are very narrow and steep and I had to lug it up to the 4th floor.

Reviewed on Nov 10, 2025

The Merchant

The Merchant

3 out of 5
Downtown Salem
Save 100% on your flight
Price was $1,125, price is now $740 per person
$740
per person
Dec 30 - Jan 3
found 16 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (375 reviews)
Incredible hospitality. One of our favorite hotel experiences in a while.

Reviewed on Nov 28, 2025

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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
$101 nightly
The price is $113 total per night from Dec 2 to Dec 3
$113 total
Dec 2 - Dec 3
Total with taxes and fees
8.6/10 Excellent! (2,146 reviews)
Nice place to stay, off season. Price was very reasonable. Room was comfortable, (1st floor, Building 5), entire building was very quiet, hardly anyone on the property. Nice amenities, but we only walked through, did not use (pool, locker rooms, hot tub, fire pit). Room was nicely appointed and comfortable. ...

Reviewed on Nov 22, 2025

Vacation Village in the Berkshires
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundable
$105 nightly
The price is $117 total per night from Dec 2 to Dec 3
$117 total
Dec 2 - Dec 3
Total with taxes and fees
9.2/10 Wonderful! (2,273 reviews)
The hotel was great. The biggest thing keeping this from being excellent was that the thermostat in the room didn't work. The fan was set to auto yet the heater kept heating until it was too hot. We had to turn it off at times and it made sleeping uncomfortably hot.

Reviewed on Nov 29, 2025

D. Hotel Suites & Spa
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $135 total per night from Dec 7 to Dec 8
$135 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (768 reviews)
When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it.

Reviewed on Nov 26, 2025

Berkshire Mountain Lodge
See all 897 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 $411 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.