Cummington Vacations from $595

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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.
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Save 100% on your flight
Price was $920, price is now $595 per person
$595
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (2,387 reviews)
Starbucks and rental car service

Reviewed on Jul 9, 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was $1,715, price is now $994 per person
$994
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,548, price is now $1,520 per person
$1,520
per person
Sep 24 - Sep 27
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $2,290, price is now $1,506 per person
$1,506
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (670 reviews)
I highly recommend this location! The staff went above and beyond the call of duty to ensure we had a wonderful stay. The service throughout the property was truly excellent.

Reviewed on Jul 9, 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was $1,002, price is now $665 per person
$665
per person
Sep 23 - Sep 26
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (177 reviews)
We had a great stay. Very friendly staff!

Reviewed on Jul 9, 2026

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Cummington Hotel Deals

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts

Cummington MA
$129 nightly
The price is $136 total per night from Jul 12 to Jul 13
$136 total
Jul 12 - Jul 13
Total with taxes and fees
10/10 Exceptional! (3 reviews)
"Spiritual, artistic home. Wonderful."

Reviewed on Jun 10, 2026

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
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
$143 nightly
The price is $159 total per night from Jul 12 to Jul 13
$159 total
Jul 12 - Jul 13
Total with taxes and fees
8.8/10 Excellent! (2,429 reviews)
"We absolutely love it there! Colleen at the front desk has been there a very long time she's sweet as can be! everyone is so nice and helpful, and the place is relaxing and clean we stay there quite often!"

Reviewed on Jul 9, 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $169 total per night from Jul 12 to Jul 13
$169 total
Jul 12 - Jul 13
Total with taxes and fees
9.2/10 Wonderful! (1,010 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."

Reviewed on Jul 9, 2026

The Yankee Inn
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 $595 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.