Cummington Vacations from $742

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Luxury Apartments by Hyatus at Boston Everett

Luxury Apartments by Hyatus at Boston Everett

5 out of 5
Save 100% on your flight
Price was $1,160, price is now $742 per person
$742
per person
Jul 31 - Aug 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (5 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

Four Seasons Hotel Boston

Four Seasons Hotel Boston

5 out of 5
Bay Village
Save 100% on your flight
Price was $2,422, price is now $1,478 per person
$1,478
per person
Sep 19 - Sep 22
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (474 reviews)
perfecto

Reviewed on Jun 8, 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Save 100% on your flight
Price was $1,882, price is now $1,176 per person
$1,176
per person
Sep 17 - Sep 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (158 reviews)
The staff is very helpful and courteous! Loved the complimentary water at check-in, checkout, and also in the fitness room. The fitness room is exceptional. Free weights, weight machines, Pelotons, quality treadmills, etc.

Reviewed on Jun 30, 2026

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was $1,342, price is now $861 per person
$861
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (256 reviews)
Quaint, lovely place to stay

Reviewed on Jun 24, 2026

The Coach House

The Coach House

3 out of 5
Save 100% on your flight
Price was $1,303, price is now $842 per person
$842
per person
Sep 5 - Sep 7
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (182 reviews)
This was my first time staying at a boutique hotel and it was a great choice. Not only was the price great, but the room was a good size and I enjoyed the snacks and toiletries. It was also very quiet— I slept very well. The Coach House is about a 20 minute walk (5-10 minute Uber) into the town square. The weather was great so I enjoyed the walks. Water was hot and pressure good.

Reviewed on Jun 15, 2026

Don't see what you're looking for?
See all available trips from Columbus to Cummington
View all trips

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
$129 nightly
The price is $136 total per night from Jul 2 to Jul 3
$136 total
Jul 2 - Jul 3
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
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
$143 nightly
The price is $159 total per night from Jul 6 to Jul 7
$159 total
Jul 6 - Jul 7
Total with taxes and fees
8.8/10 Excellent! (2,412 reviews)
"Staff was super friendly, splash pad was being renovated so that wasn’t available m.. we had fun but hate that check in is so late and check out so early!"

Reviewed on Jun 30, 2026

Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
$155 nightly
The price is $173 total per night from Jul 8 to Jul 9
$173 total
Jul 8 - Jul 9
Total with taxes and fees
9.2/10 Wonderful! (1,011 reviews)
"The friendly atmosphere coming from the staff."

Reviewed on Jun 30, 2026

The Yankee Inn
See all 900 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Cummington vacation package cost?
You'll find cheap prices from $742 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.