
Cummington Vacations from $296
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.


Raffles Boston
Back Bay
Price was $1,517, price is now $793 per person
$793
per person
Dec 19 - Dec 23
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (160 reviews)
I wish the water was hotter, had to ask to have room cleaned after 1st day as housekeeping did not come. Very responsive though when inquiries made.
Reviewed on Oct 7, 2025


Beacon Hill Hotel
Beacon Hill
Save 100% on your flight
Price was $837, price is now $535 per person
$535
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (246 reviews)
Lean room, nice staff but the elevator broke and it took a while to fix it
Reviewed on Oct 1, 2025

The Charles Hotel
West Cambridge
Save 100% on your flight
Price was $823, price is now $532 per person
$532
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,005 reviews)
Clean, easy check in, quiet, in walking distance of everything we need-our favorite place to stay always!
Reviewed on Oct 11, 2025
Cummington Hotel Deals

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $125 total per night from Oct 30 to Oct 31
$125 total
Oct 30 - Oct 31
Total with taxes and fees
8.6/10 Excellent! (2,049 reviews)
Check-in Needs Improvement
"Why have an on-line pre-check process if you have to wait in a long line when you arrive. Need to have separate line(s) for those who pre-check."
Reviewed on Oct 11, 2025

Hotel Downstreet, an Ascend Collection Hotel
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $145 total per night from Nov 11 to Nov 12
$145 total
Nov 11 - Nov 12
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Super friendly staff, a free coffee bar in the lobby, loads of food and shopping options within walking distance, free on-site parking - what’s not to love! And the room was spotlessly clean and very very comfortable. We love this place!!!"
Reviewed on Oct 9, 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $118 total per night from Nov 3 to Nov 4
$118 total
Nov 3 - Nov 4
Total with taxes and fees
8.8/10 Excellent! (677 reviews)
"Great stay, perfect"
Reviewed on Oct 6, 2025
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.
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 |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Hotels near Swift River
- Plainfield Hotels
- Cabin Rentals in Plainfield
- 5 Star Hotels in Plainfield
- Resorts in Plainfield
- Hotels near Chesterfield Gorge
- Worthington Hotels
- Resorts in Worthington
- 5 Star Hotels in Worthington
- B&B in Worthington
- Cabin Rentals in Worthington
- 4 Star Hotels in Worthington
- Guest Houses in Worthington
- Goshen Hotels
- Cabin Rentals in Goshen
- B&B in Goshen
- Motels in Goshen
- Vacation Homes in Goshen
- Chesterfield Hotels
- 5 Star Hotels in Chesterfield
- 3 Star Hotels in Chesterfield
- 4 Star Hotels in Chesterfield
- Cottages in Chesterfield
- Farmstay in Chesterfield
- Cabin Rentals in Chesterfield
- Hotels near Chapel Brook
- Hotels near Ashfield Lake
- Hotels near Double Edge Theatre
- Ashfield Hotels
- Cabin Rentals in Ashfield
- B&B in Ashfield
- Apartments in Ashfield
- Cottages in Ashfield
- Motels in Ashfield
- Western Massachusetts Hotels
- Resorts & Hotels with Spas in Western Massachusetts
- Luxury Hotels in Western Massachusetts
- Romantic Hotels in Western Massachusetts
- Hotels with an Indoor Pool in Western Massachusetts
- Cabin Rentals in Western Massachusetts
- Pet-friendly Hotels in Western Massachusetts
- Hotels on the Lake in Western Massachusetts
- B&B in Western Massachusetts
- Golf Hotels in Western Massachusetts
- Hotels with a View in Western Massachusetts
- Cheap Hotels in Western Massachusetts
- Hotels with Hot Tubs in Western Massachusetts
- Adults Only Resorts & in Western Massachusetts
- Boutique Hotels in Western Massachusetts
- Hotel Wedding Venues Hotels in Western Massachusetts
- Historic Hotels in Western Massachusetts
- Hotels with Restaurants in Western Massachusetts
- Ski Hotels in Western Massachusetts
- Hotels with a Pool in Western Massachusetts
- Honeymoon Resorts & in Western Massachusetts
- Winery Hotels in Western Massachusetts
- RV Parks in Western Massachusetts
- 4 Star Hotels in Western Massachusetts
- Hotels with Suites in Western Massachusetts
- Condo Rentals in Western Massachusetts
- Apartments in Western Massachusetts
- Hotels with Waterslides in Western Massachusetts
- 5 Star Hotels in Western Massachusetts
- Extended Stay Hotels in Western Massachusetts
- Motels in Western Massachusetts
- Hotels with Fireplaces in Western Massachusetts
- Waterpark Hotels in Western Massachusetts
- Cottages in Western Massachusetts
- Resorts in Western Massachusetts
- Hotels with an Outdoor Pool in Western Massachusetts
- Car rentals near Plainfield
- Car rentals near Worthington
- Car rentals near Goshen
- Car rentals near Chesterfield
- Car rentals near Ashfield Lake
- Car rentals near Ashfield
- Car rentals near Western Massachusetts
- Dollar Rent A Car Rental Cars in Western Massachusetts
- Localiza Rental Cars in Western Massachusetts
- Enterprise Rental Cars in Western Massachusetts
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.