Cummington Vacations from $527
Book a Hotel + Flight or Car together to unlock savings
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 Lodge and Suites
Dorchester
$527
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Luxury Apartments by Hyatus at Boston Everett
$1,398
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (6 reviews)
We were in Boston for the Mammoth March in Hingham and needed a base for some sight seeing in Boston for the week.
We did not have a rental car but the parking garage was easily accessible and secure.
We were able to get ubers very easily from the location.
The Chelsea train station was only a 5 min walk away and the trains were reliable and efficient.
The support staff replied to all our messages in the chat option quickly and were very helpful.
The kitchen was well stocked and set up. The apartment was clean and all the linens and towels were freshly laundred.
Would recommend this place without hesitation.
Reviewed on Jun 15, 2026
The Inn at Hastings Park, Relais & Chateaux - Boston
$1,716
per person
Oct 15 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Boston (BOS)
9.6/10 Exceptional! (262 reviews)
This Inn is a beautiful old building with a long history. It is located within easy walking distance of downtown Lexington with all its history. The Inn had wonderful rooms, a great staff and a top rate restaurant all in one place. Highly recommend!
Reviewed on Jul 13, 2026
Don't see what you're looking for?
See all available trips from Pretty Prairie to Cummington
View all tripsCummington Hotel Deals
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Fully refundableReserve now, pay when you stay
$128 nightly
$143 total
Aug 31 - Sep 1
Total with taxes and fees
D. Hotel Suites & Spa
1 Country Club Rd Holyoke MA
Fully refundable
$142 nightly
$158 total
Aug 17 - Aug 18
Total with taxes and fees
The Yankee Inn
461 Pittsfield Rd Lenox MA
$137 nightly
$153 total
Aug 9 - Aug 10
Total with taxes and fees
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 |
More vacations you might like
Frequently asked questions
How much does a Cummington vacation package cost?
You'll find cheap prices from $527 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.
Explore a world of travel with Expedia
- Amherst Hotels
- Lodges in Cummington
- Resorts & Hotels with Spas in Western Massachusetts
- Hotels near Berkshire East Ski Resort
- Hotels with Hot Tubs in Western Massachusetts
- B&B in Plainfield
- Hotels near Tanglewood Music Center
- Pittsfield Hotels
- West Springfield Hotels
- B&B in Western Massachusetts
- Cummington Hotels
- Greenfield Hotels
- Luxury Hotels in Western Massachusetts
- Motels in Plainfield
- B&B in Worthington
- Lee Hotels
- Shelburne Falls Hotels
- 4 Star Hotels in Plainfield
- Charlemont Hotels
- Chesterfield Hotels
- Castles in Worthington
- Cabin Rentals in Ashfield
- Hotels near University of Massachusetts Amherst
- Golf Hotels in Western Massachusetts
- B&B in Cummington
- Historic Hotels in Cummington
- Rv Parks in Chesterfield
- Pet-Friendly Hotels in Western Massachusetts
- Plainfield Hotels
- Hotels with an Indoor Pool in Western Massachusetts
- Hotels & Resorts for Couples in Goshen
- Hotel Wedding Venues Hotels in Western Massachusetts
- Springfield Hotels
- Worcester Hotels
- Cabin Rentals in Goshen
- Vacation Homes in Worthington
- Deerfield Hotels
- Romantic Hotels in Western Massachusetts
- Motels in Cummington
- Northampton Hotels
- Holyoke Hotels
- North Adams Hotels
- Hadley Hotels
- Inns in Worthington
- Hotels near Swift River
- Ashfield Hotels
- Worthington Hotels
- Cabin Rentals in Western Massachusetts
- Lenox Hotels
- Cabin Rentals in Cummington
- Williamstown Hotels
- Goshen Hotels
- Shelburne Falls Vacations
- Visit Cummington
- Visit Western Massachusetts
- Deerfield Vacations
- Wahconah Falls State Park
- Adams Vacations
- Crane Museum of Papermaking
- Visit Chesterfield
- Berkshire East Ski Resort
- Northampton Vacations
- Cheshire Vacations
- Kushi Institute
- Hinsdale Vacations
- Conway Town Park
- Susan B. Anthony Birthplace Museum
- Arms Cemetery
- Deerfield Academy
- Visit Shelburne Falls
- Glendale Falls
- Goshen Vacations
- Smith College Botanic Garden
- Chesterfield Gorge
- Visit Worthington
- Great Wolf Lodge Waterpark
- Bald Mountain Pottery
- Drury Vacations
- Bardwell's Ferry Bridge
- Salmon Falls
- Bridge of Flowers
- Zoar Outdoor/Deerfield Valley Canopy Tours
- Historic Deerfield Village
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.