Cummington Vacation Packages

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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.

Top Cummington Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,062, price is now CA $590 per person
CA $590
per person
Nov 1 - Nov 3
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was CA $1,563, price is now CA $1,038 per person
CA $1,038
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
Phil’s property is immaculate and the rooms are very clean and will all required amenities. Phil’s hospitality is also top notch and it will be my place to stay in my future cape cod visits!!

Reviewed on Aug. 20, 2025

Cambria Hotel & Suites Plymouth

Cambria Hotel & Suites Plymouth

3 out of 5
Price was CA $994, price is now CA $679 per person
CA $679
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (18 reviews)
We’d love to come back here.

Reviewed on Aug. 22, 2025

Parker Beach Lodge

Parker Beach Lodge

3 out of 5
Bass River
Price was CA $1,051, price is now CA $725 per person
CA $725
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
8.4/10 Very Good! (319 reviews)
Great stay at an amazing locations. No issues we had a blast. They were so welcoming and inviting and the room was clean and comfortable.

Reviewed on Aug. 23, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was CA $1,545, price is now CA $1,078 per person
CA $1,078
per person
Oct 24 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8/10 Very Good! (585 reviews)
The location was great and we were able to get to all the sites easily. Also, liked having two beds and two bathrooms for the price. However, everything was very cheap in there. The sheets were nubbie because they were cheap and worn. The toliet paper was so awful we had to buy our own. The beds had little support. The place was clean though. So if you don't care much about the bed, sheets, and toliet paper it is a good pick. If you do maybe pick somewhere else.

Reviewed on Aug. 17, 2025

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Cummington Hotel Deals

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
The price is CA $147 per night from Sep 11 to Sep 12
CA $147
CA $180 total
Sep 11 - Sep 12
includes taxes & fees
8.6/10 Excellent! (1,961 reviews)
"The property was nice and had activities like a volley ball net and basketball court however no balls were provided. All together the property was very nice but had potential to be nicer. Also daytime front desk staff were not very helpful and actually cranky sounding. Not so pleasant to deal ..."

Reviewed on Aug. 20, 2025

Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Sep 7 to Sep 8
CA $106
CA $149 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (583 reviews)
Satisfied customer
"as good as the last time we stayed there."

Reviewed on Aug. 21, 2025

Berkshire Mountain Lodge
D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
1 Country Club Rd, Holyoke, MA
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Sep 1 to Sep 2
CA $170
CA $197 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,218 reviews)
"Consistently excellent stay"

Reviewed on Aug. 22, 2025

D. Hotel Suites & Spa
See all 906 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Cummington vacation package cost?
You can snap up a vacation package to this popular destination from CA $590 on Expedia. But how much your vacation to Cummington costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Cummington?
If you're hoping to book a cheap Cummington vacation package, consider visiting in January, February and November. You'll generally find lower rates on hotels and flights during these quieter months — perfect for a budget-friendly break.
How many days is enough for Cummington?
The ideal length of your Cummington vacation depends on what you'd like to do. Usually, a handful of days to a week will give you enough time to visit all the top sights and explore some hidden spots along the way.
How to find the best Cummington package deals?
Landing a cheap Cummington package deal is a cinch with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most economical Cummington package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Cummington vacation as a package?
An Expedia vacation package could land you significant savings when compared to booking accommodations and flights separately. Better still, you can tailor your Cummington trip to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Cummington?
Secure incredible discounts by reserving your flights early with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for an impromptu Cummington break.
How to plan a trip to Cummington?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Cummington.
  2. Plan your budget wisely: As well as the cost of your stay, you'll need to consider other expenses. These include transportation, flights and food. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Cummington.
  3. Decide how many days away: Start by making a list of all the attractions and activities you want to experience in Cummington. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Cummington vacation package that brings all your bookings together.

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