
Cummington Vacations from $319
Book a Hotel + Flight or Car together to unlock savings
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.


Boston Harbor Hotel
North End
Save 100% on your flight
Price was $1,333, price is now $786 per person
$786
per person
Nov 3 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Great location. Beautiful building and setting. Staff are helpful and friendly!
Reviewed on Aug 24, 2025

DoubleTree by Hilton Boston North Shore
Save 100% on your flight
Price was $882, price is now $569 per person
$569
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8/10 Very Good! (2,072 reviews)
Good value for the price and our family of 5. I would prefer rooms with no carpet. It was fine, but questionable as I smelled chorine. Overall, it was fine. The front desk was helpful and the service was very good.
Reviewed on Aug 21, 2025

Fairfield Inn & Suites by Marriott Plymouth
Save 100% on your flight
Price was $603, price is now $390 per person
$390
per person
Nov 12 - Nov 17
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
8.8/10 Excellent! (474 reviews)
Clean and comfortable. Very easy to park.
Reviewed on Aug 5, 2025

Fairmont Copley Plaza, Boston
Back Bay
Save 100% on your flight
Price was $2,029, price is now $1,328 per person
$1,328
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.8/10 Excellent! (1,040 reviews)
A classic hotel - well situated- everything was very relaxed . They could benefit from having another bar or sports bar
Reviewed on Aug 25, 2025
Cummington Hotel Deals

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $145 total per night from Sep 1 to Sep 2
$145 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (1,970 reviews)
"The staff at Vacation Village are simply amazing! Super nice and very helpful. Very clean, lots of amenities, and spacious rooms! Will definitely stay again!"
Reviewed on Aug 24, 2025

Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (586 reviews)
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."
Reviewed on Aug 23, 2025

D. Hotel Suites & Spa
1 Country Club Rd, Holyoke, MA
$150 nightly
The price is $168 total per night from Sep 1 to Sep 2
$168 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (2,219 reviews)
"Clean hotel, large room, comfortable bed, great breakfast"
Reviewed on Aug 24, 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.
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
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.