Cummington Vacations from $988

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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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was $1,711, price is now $988 per person
$988
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,009 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

Nantucket Inn

Nantucket Inn

3.5 out of 5
Save 100% on your flight
Price was $2,324, price is now $1,355 per person
$1,355
per person
Sep 3 - Sep 7
found 16 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (711 reviews)
It would be nice to include bottled water in the room. Expected a little more for paying $1k/nt. Staff were courteous. The shuttle is helpful and convenient to airport.

Reviewed on Jun 19, 2026

The Coach House

The Coach House

3 out of 5
Save 100% on your flight
Price was $1,826, price is now $1,087 per person
$1,087
per person
Sep 5 - Sep 8
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (182 reviews)
Everything was perfect

Reviewed on Jun 12, 2026

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was $2,119, price is now $1,286 per person
$1,286
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,001 reviews)
had a delicious muffin and coffee. Parking was safe and convenient.

Reviewed on Jun 22, 2026

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $3,636, price is now $2,270 per person
$2,270
per person
Aug 29 - Sep 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (428 reviews)
The valet was fast and professional, the room was clean, the staff are very helpful. I would definitely stay again!

Reviewed on May 25, 2026

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Cummington Hotel Deals

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

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 29 to Jun 30
$136 total
Jun 29 - Jun 30
Total with taxes and fees
10/10 Exceptional! (3 reviews)
"Spiritual, artistic home. Wonderful."

Reviewed on Jun 10, 2026

Artistic, Pet-Friendly Getaway in the Foothills of the Berkshire Mountains of Massachusetts
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd Holyoke MA
Fully refundable
$132 nightly
The price is $147 total per night from Jun 30 to Jul 1
$147 total
Jun 30 - Jul 1
Total with taxes and fees
9.2/10 Wonderful! (2,136 reviews)
"Excellent staff. Location is not all that convenient to Amherst or Holyoke. Property and decor were pleasant but need a refresh."

Reviewed on Jun 26, 2026

D. Hotel Suites & Spa
Hotel UMass

Hotel UMass

2.5 out of 5
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! (1,001 reviews)
"Really convenient"

Reviewed on Jun 24, 2026

Hotel UMass
See all 897 properties in Cummington
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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Frequently asked questions

How much does a Cummington vacation package cost?
You'll find cheap prices from $988 on Expedia for your Cummington escape. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Cummington costs.
What are the cheapest months to go to Cummington?
You're likely to find lower rates and better availability in January, October and December. Browse our cheap Cummington vacation packages and you could score some great off-season deals.
How many days is enough for Cummington?
Generally, a handful of days is enough to see the top attractions during your Cummington vacation. But if you prefer to have time to chill out or take day trips, consider extending your itinerary.
How to find the best Cummington package deals?
Finding a cheap Cummington package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Cummington package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Cummington vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Cummington vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Cummington?
Score incredible bargains by booking your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Cummington getaway.
Does Expedia offer Book Now, Pay Later Cummington vacation packages?
Set off on your ideal getaway to Cummington with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next payday — we've joined forces with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snap up travel deals before they disappear.

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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.