Cummington Vacations from $880

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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
Save 100% on your flight
Price was $1,393, price is now $880 per person
$880
per person
Jul 21 - Jul 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again

Reviewed on May 25, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was $2,417, price is now $1,290 per person
$1,290
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (256 reviews)
Splendid bed and breakfast

Reviewed on Apr 29, 2026

Briar Barn Inn

Briar Barn Inn

3.5 out of 5
Save 100% on your flight
Price was $1,543, price is now $1,013 per person
$1,013
per person
Jul 14 - Jul 21
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (792 reviews)
Every aspect of the rooms and service had an extra level of thought behind them. The Nespresso machines were a nice surprise. The lobby had ice all the time so make iced coffees; they were great for on-the-go mornings. The toiletries and diffusers all used very pleasant essential oils that were calming and not intrusive.

Reviewed on May 25, 2026

Furnished Apartment Near Longwood

Furnished Apartment Near Longwood

3 out of 5
North Brookline
Save 100% on your flight
Price was $1,413, price is now $931 per person
$931
per person
Jul 31 - Aug 5
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
7.4/10 Good! (3 reviews)
Easy to check in, students friendly apartment, convenient location, easy to call Uber or Lyft, and within 20 min. drive to the famous universities.

Reviewed on Apr 1, 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was $1,571, price is now $1,051 per person
$1,051
per person
Aug 4 - Aug 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,241 reviews)
Gorgeous hotel in a fabulous location. Highly recommend!

Reviewed on May 19, 2026

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Cummington Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $143 total per night from Jun 25 to Jun 26
$143 total
Jun 25 - Jun 26
Total with taxes and fees
9/10 Wonderful! (950 reviews)
"Clean room. Very well equipped. It is a hidden gem, close to everything. Great experience"

Reviewed on May 26, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
$119 nightly
The price is $133 total per night from May 27 to May 28
$133 total
May 27 - May 28
Total with taxes and fees
9/10 Wonderful! (959 reviews)
"Great location, clean and spacious room, lobby area was very relaxing! We enjoyed the coffee available at the front as well."

Reviewed on May 24, 2026

Berkshires Untold
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$128 nightly
The price is $143 total per night from May 27 to May 28
$143 total
May 27 - May 28
Total with taxes and fees
8.8/10 Excellent! (2,369 reviews)
"Been coming every Memorial Day. Great value for families"

Reviewed on May 25, 2026

Vacation Village in the Berkshires
See all 916 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 $880 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.