Cummington Vacations from $858

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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 Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,354, price is now $858 per person
$858
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (256 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $2,382, price is now $1,197 per person
$1,197
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again

Reviewed on May 25, 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $4,414, price is now $2,569 per person
$2,569
per person
Aug 4 - Aug 11
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Staff was very nice and helpful.

Reviewed on May 28, 2026

Nantucket Inn

Nantucket Inn

3.5 out of 5
Price was $3,104, price is now $2,020 per person
$2,020
per person
Aug 8 - Aug 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (692 reviews)
The staff went above and beyond... So helpful and courteous! Our room was spacious and immaculate, and the indoor pool and hot tub was an added bonus! Nice small bar attached to the lobby with a little restaurant for breakfast and lunch... we'll be back for sure!

Reviewed on Jun 1, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,505, price is now $999 per person
$999
per person
Aug 18 - Aug 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,007 reviews)
Fantastic Hotel. Loved the location, room was clean, staff was helpful, and loved the amenities.

Reviewed on May 25, 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
Fully refundable
$128 nightly
The price is $135 total per night from Jun 8 to Jun 9
$135 total
Jun 8 - Jun 9
Total with taxes and fees
10/10 Exceptional! (2 reviews)
"It is an Artist’s Retreat. It is very quirky, but once you get used to it, it was great. Dog friendly, brought my boxer, large back space to walk them in. Right on river, absolutely peaceful.My only thing is none of the rooms have two beds, and I was traveling with my brother. Not sleep in’ in a ..."

Reviewed on May 17, 2026

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

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $166 total per night from Jul 5 to Jul 6
$166 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (961 reviews)
"Water pressure in shower overwhelmingly strong"

Reviewed on Jun 2, 2026

Berkshire Mountain Lodge
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
$145 nightly
The price is $162 total per night from Jun 7 to Jun 8
$162 total
Jun 7 - Jun 8
Total with taxes and fees
8.8/10 Excellent! (2,389 reviews)
"Great place just listed again for four more nights"

Reviewed on Jun 3, 2026

Vacation Village in the Berkshires
See all 887 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 $858 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.