
Cummington Vacations from $1,209
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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.

Fairmont Copley Plaza, Boston
Back Bay
Save 100% on your flight
Price was $1,839, price is now $1,209 per person
$1,209
per person
Jul 28 - Aug 2
found 21 hours ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
9/10 Wonderful! (1,243 reviews)
Gorgeous hotel in a fabulous location. Highly recommend!
Reviewed on May 19, 2026

By the Sea Guests Bed & Breakfast & Suites
Save 100% on your flight
Price was $3,391, price is now $1,943 per person
$1,943
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!
Reviewed on Sep 20, 2025

Nantucket Inn
Save 100% on your flight
Price was $3,306, price is now $2,013 per person
$2,013
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9/10 Wonderful! (684 reviews)
The shuttle goes downtown so often and the staff is amazing
Reviewed on May 22, 2026

Beachside Village Resort
Save 100% on your flight
Price was $2,123, price is now $1,388 per person
$1,388
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (104 reviews)
Beautiful ocean view. Cozy studio with everything you need. Full kitchen, super comfortable beds, room darkening curtains. We rented there due to the location to both ferries. We could ride our bikes to either pier and also downtown. Will return!
Reviewed on May 18, 2026

Chatham Tides
Save 100% on your flight
Price was $2,661, price is now $1,755 per person
$1,755
per person
Aug 6 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (691 reviews)
Beautiful place with a great view and a very peaceful atmosphere. The hotel is old and rustic, but that’s also part of its charm. If you’re looking for an authentic seaside style experience, it’s warm and cozy and fits the vibe perfectly.
However, the beach right in front of the hotel is probably the dirtiest in the area. There were many dead marine animal and seaweeds remains along the shore and which made it unpleasant to walk on or fully enjoy. For nicer beaches, expect about a 20-minute drive.
As for the hotel itself, I still enjoyed my stay overall. That said, the plumbing is very noisy — you can hear every time neighboring rooms use water — and there is almost no sound insulation between rooms.
Reviewed on May 21, 2026
Cummington Hotel Deals

Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from May 25 to May 26
$126 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (944 reviews)
"The rooms were so spacious, with a great kitchen full of dishware to use. The Staff were so kind, helpful and knowledgeable."
Reviewed on May 21, 2026

Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $124 total per night from May 25 to May 26
$124 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (952 reviews)
"all very good for our 1 night stay!!"
Reviewed on May 20, 2026

Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $123 total per night from May 25 to May 26
$123 total
May 25 - May 26
Total with taxes and fees
8.8/10 Excellent! (2,362 reviews)
"Nice staff, nice room and facilities. Having stayed there several times happily and will be back again in June. Thanks."
Reviewed on May 22, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.



















