
Hawley Vacation Packages
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Your Hawley Vacation
When a getaway to the city is calling your name, answer it with a vacation package to Hawley. With all your travel arrangements organized before you go, all you have to do here is focus on having a blast. Every trip to Hawley needs a well-planned itinerary. Fill yours with major attractions such as Berkshire East Ski Resort, Charlemont Federated Church and Hawley Bog Preserve. Whoever you're going away with and whatever you want to spend, your dream Hawley vacation is just clicks away with Expedia.
Top Hawley Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Lakeside Inn
Price was CA $1,094, price is now CA $703 per person
CA $703
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (2,162 reviews)
We stayed for one night. When we arrived the restaurant was just jumping with excitement with families and others singing karaoke. It was a nice welcome. We checked out the pool. It was a little cold but the kids had a quick dip and were happy. The staff was amazing. Such great customer service. From the staff that checked us in, the gentleman that cooked breakfast and the lady that cleaned the rooms. The maintenance man helped us with a little issue faster than my toddler could asking him a million questions which is lightning speed. Checkout was also great! 10/10 would definitely stay here again. Rooms were comfortable, quiet, and clean! Great water pressure for the kids baths and showers.
Reviewed on Aug. 28, 2025


Raffles Boston
Back Bay
Price was CA $2,781, price is now CA $1,651 per person
CA $1,651
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
I could not fault this hotel in any way. After long days out sightseeing and shopping it was great to get back and relax. This was our first time in Boston so we’re not sure which area was best to stay in. However the hotel’s location in Back Bay was excellent.
Reviewed on Aug. 28, 2025


Sesuit Harbor House
Price was CA $1,406, price is now CA $911 per person
CA $911
per person
Oct 23 - Oct 27
found 1 hour ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (168 reviews)
We’ve been to the Cape many times over the past 20 years. The Sesuit Harbor House was conveniently located off Route 6a, but it was very quiet; you couldn’t hear the traffic at all. Phil and his staff are very attentive and friendly; the continental breakfast in a basket every morning (with local treats) was perfect! We will come back and hopefully with more family members. It was 10/10!
Reviewed on Aug. 25, 2025
Hawley Hotel Deals

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Hawley

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $80 per night from Sep 11 to Sep 12
CA $80
CA $105 total
Sep 11 - Sep 12
includes taxes & fees

Berkshire Mountain Lodge
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! (598 reviews)
"The staff was friendly and helpful it was easy to get in and out and convenient to get around."
Reviewed on Aug. 27, 2025
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.
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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.