Cummington Vacations from $951

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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.
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Save 100% on your flight
Price was $1,603, price is now $951 per person
$951
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (2,370 reviews)
Great location for visiting Cambridge and just a short walk across the bridge to Fenway Park.

Reviewed on Jun 26, 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 1 day 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 $1,920, price is now $1,156 per person
$1,156
per person
Aug 29 - Sep 4
found 20 hours 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

The Godfrey Hotel Boston

The Godfrey Hotel Boston

4 out of 5
Downtown Boston
Save 100% on your flight
Price was $2,027, price is now $1,245 per person
$1,245
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (5,092 reviews)
Great place and location, all the staff were amazing.

Reviewed on Jun 27, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was $2,055, price is now $1,276 per person
$1,276
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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

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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
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$154 nightly
The price is $172 total per night from Jun 30 to Jul 1
$172 total
Jun 30 - Jul 1
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"No real breakfast"

Reviewed on Jun 21, 2026

Hotel Downstreet, an Ascend Collection Hotel
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $158 total per night from Jul 5 to Jul 6
$158 total
Jul 5 - Jul 6
Total with taxes and fees
8.8/10 Excellent! (2,409 reviews)
"The room was great. Had everything I needed and was very comfortable."

Reviewed on Jun 24, 2026

Vacation Village in the Berkshires
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 $951 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.