
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 1 day 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

The Inn at Hastings Park, Relais & Chateaux - Boston
Save 100% on your flight
Price was $1,270, price is now $744 per person
$744
per person
Aug 23 - Aug 27
found 9 hours ago
Roundtrip flight included
New York (NYC) to Boston (BOS)
9.6/10 Exceptional! (256 reviews)
Splendid bed and breakfast
Reviewed on Apr 29, 2026

Sea Crest Beach Resort
Save 100% on your flight
Price was $1,130, price is now $676 per person
$676
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
7.8/10 Good! (301 reviews)
We recently stayed at the Sea Crest in Falmouth and overall had a nice experience. The biggest downside was check-in. Our room wasn't ready until much later than expected, and we didn't receive a text that it was available until 6:15 PM. Many guests appeared frustrated, and the staff seemed stressed as they handled numerous complaints about the delayed check-in process.
That said, we were able to use the pools and other amenities while we waited, which helped make the delay more manageable. Our room was clean, a good size, and had very comfortable bedding. The indoor and outdoor pools were well maintained, and we especially enjoyed the heated outdoor pool. We also had a great time listening to a live band on the outdoor deck.
The private beach was clean and had plenty of loungers available for guests. Food and drink prices at the bar and restaurant were a bit inflated, but it was very convenient to have everything right on-site.
Despite the check-in issues, the amenities, beach, pools, and comfortable accommodations made for an enjoyable stay.
Reviewed on Jun 22, 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 1 day 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

Eurostars The Boxer
West End
Save 100% on your flight
Price was $2,032, price is now $1,299 per person
$1,299
per person
Sep 4 - Sep 9
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.8/10 Excellent! (1,524 reviews)
Very nice hotel. Clean, functional and a great place for a romantic trip. Would absolutely stay there again.
Reviewed on Jun 19, 2026
Cummington Hotel Deals

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
Cummington MA
$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

D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundable
$132 nightly
The price is $147 total per night from Jun 29 to Jun 30
$147 total
Jun 29 - Jun 30
Total with taxes and fees
9.2/10 Wonderful! (2,153 reviews)
"Great place"
Reviewed on Jun 21, 2026

Hotel UMass
1 Campus Center Way Amherst MA
Fully refundable
$144 nightly
The price is $161 total per night from Jul 2 to Jul 3
$161 total
Jul 2 - Jul 3
Total with taxes and fees
8.8/10 Excellent! (1,012 reviews)
"Not good, definitely not even close to worth the inflated fee we were charged. How expedia has this rated so good is a mystery. On par with a red roof or such and a hassle finding it and getting in. No real lobby, through an underground parking garage and a maze."
Reviewed on Jun 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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