Cummington Vacations from $610

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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.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Save 100% on your flight
Price was $988, price is now $610 per person
$610
per person
Jun 24 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was $4,121, price is now $2,587 per person
$2,587
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (419 reviews)
This is not a blow, your socks off property by any means! Dated and just ok. You’ll get the same thing for far less expense at a Sheraton, Hilton or Hyatt. Staff waa nice. There was nothing bad but certainly nothing spectacular or memorable to rave about.

Reviewed on Apr 29, 2026

Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was $1,260, price is now $798 per person
$798
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.4/10 Very Good! (1,441 reviews)
The area is very good for walking and getting the sense of Boston. The rooms are clean and most importantly the staff is excellent.

Reviewed on May 8, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $2,150, price is now $1,399 per person
$1,399
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Service both at the hotel and restaurants was the one of the best experiences I’ve had

Reviewed on May 2, 2026

Summer House Hotel

Summer House Hotel

2 out of 5
Save 100% on your flight
Price was $1,819, price is now $1,256 per person
$1,256
per person
Jun 24 - Jun 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Boston (BOS)
No reviews
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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
$113 nightly
The price is $126 total per night from May 24 to May 25
$126 total
May 24 - May 25
Total with taxes and fees
9/10 Wonderful! (930 reviews)
These are all 1 bedroom suites. There was plenty of room in kitchen cupboards for our groceries. The kitchen was well supplied with cooking utensils, dishes and glassware. The location is excellent with several grocery stores and restaurants close by. Everything was perfect except for the height ...

Reviewed on May 11, 2026

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $121 total per night from May 14 to May 15
$121 total
May 14 - May 15
Total with taxes and fees
9/10 Wonderful! (937 reviews)
we would have had breakfast there but it is a limited menu. Beautiful hotel staff is very friendly. This is my second visit and plan to return :)

Reviewed on May 11, 2026

Berkshires Untold
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
$110 nightly
The price is $123 total per night from May 12 to May 13
$123 total
May 12 - May 13
Total with taxes and fees
8.8/10 Excellent! (2,355 reviews)
Everything was great!

Reviewed on May 10, 2026

Vacation Village in the Berkshires
See all 909 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 $610 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.