
Cummington Vacations from $531
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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.

By the Sea Guests Bed & Breakfast & Suites
Save 100% on your flight
Price was $861, price is now $531 per person
$531
per person
Aug 28 - Aug 31
found 3 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (188 reviews)
It is truly a bed and breakfast. We stayed in the main house in a cozy upstairs updated bedroom overlooking the ocean. Breakfast was served every morning between 8am and 10am. Allowing us to have our coffee and stroll along the beach before our meal. Staff friendly and helpful. We will return again next year
Reviewed on Jun 18, 2026

Good Hotels Boston
South End
Save 100% on your flight
Price was $1,044, price is now $606 per person
$606
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Chicago (CHI) 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

Beachside Village Resort
Save 100% on your flight
Price was $1,019, price is now $632 per person
$632
per person
Aug 28 - Aug 31
found 3 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.4/10 Exceptional! (111 reviews)
This property was extraordinary. My late check-in was seamless, and my room was spacious and extremely comfortable. The staff (my apologies, I forgot the front desk staff's names) were friendly, helpful, and professional. I had one minor maintenance issue that Joe resolved promptly and courteously. My room was directly across from the water, so I had a great view from my room and balcony. Having a kitchen made me feel right at home. My local friends, etc., were extremely impressed by the property layout, location, and price. Downtown was within walking distance (about a mile), and the beach was nearby. I will definitely plan a return visit here, but it would be hard to top my last stay.
Reviewed on Jun 5, 2026

Boston Harbor Hotel
North End
Save 100% on your flight
Price was $3,219, price is now $2,029 per person
$2,029
per person
Jul 21 - Jul 26
found 2 days ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,003 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent
Reviewed on Jun 15, 2026

Cummington Hotel Deals

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Cummington MA
Fully refundable
$129 nightly
The price is $136 total per night from Jun 24 to Jun 25
$136 total
Jun 24 - Jun 25
Total with taxes and fees
10/10 Exceptional! (3 reviews)
"Spiritual, artistic home. Wonderful."
Reviewed on Jun 10, 2026

Hotel UMass
1 Campus Center Way Amherst MA
Fully refundable
$141 nightly
The price is $157 total per night from Jul 7 to Jul 8
$157 total
Jul 7 - Jul 8
Total with taxes and fees
8.8/10 Excellent! (1,009 reviews)
"Had a great stay."
Reviewed on Jun 21, 2026

D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundable
$128 nightly
The price is $143 total per night from Jun 30 to Jul 1
$143 total
Jun 30 - Jul 1
Total with taxes and fees
9.2/10 Wonderful! (2,149 reviews)
"Great place"
Reviewed on Jun 21, 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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