Hawley Vacations from $343

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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.

The Latest Hawley vacation packages

Price found within the past 48 hours. Click for updated prices.
The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Save 100% on your flight
Price was $490, price is now $343 per person
$343
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.2/10 Wonderful! (1,160 reviews)
Courteous staff, great work out room, nice rooms!

Reviewed on Mar 1, 2026

AutoCamp Cape Cod

AutoCamp Cape Cod

4 out of 5
Save 100% on your flight
Price was $857, price is now $577 per person
$577
per person
May 19 - May 24
found 18 hours ago
Roundtrip flight included
Chicago (ORD) to Boston (BOS)
9.4/10 Exceptional! (305 reviews)
We had a wonderful stay here on Valentine’s Day weekend. It was the first time we stayed at a camp ground and definitely the first time staying in an AirStream. The clubhouse was sooo nice! Staff were great. Good menu options and merch as well. Picked up an AutoCamp beanie! Live music was awesome. My only complaint is we had no hot water! That was tough being that we are in the middle of the winter and it was already freezing outside. Hot showers would have been nice! Other than that we’re planning for a summer weekend here

Reviewed on Feb 17, 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 $1,287, price is now $871 per person
$871
per person
Apr 3 - Apr 7
found 22 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (247 reviews)
Beautiful property! Room was excellent. Great amenities and free continental breakfast brought to our room.

Reviewed on Oct 21, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $1,055, price is now $726 per person
$726
per person
Apr 3 - Apr 5
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

Furnished Apartment near BMC

Furnished Apartment near BMC

3 out of 5
South End
Price was $1,830, price is now $1,272 per person
$1,272
per person
May 16 - May 23
found 1 hour ago
Roundtrip flight included
Miami (MIA) to Boston (BOS)
No reviews
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Discover the most popular places to visit in Hawley

hawley bog nature preserve Massachusetts

Hawley Bog Preserve

Explore the great outdoors at Hawley Bog Preserve, a lovely green space in Hawley. Wander the forest or discover the area's waterfalls.

Hawley Bog Preserve
Bissell covered bridge

Bissell Covered Bridge

Learn about the local history of Charlemont with a stop at Bissell Covered Bridge. Wander the forest or discover the area's waterfalls.

Bissell Covered Bridge

Berkshire East Ski Resort

4.5/5(30 reviews)

Hit the slopes in Charlemont with a visit to Berkshire East Ski Resort. Wander the forest or discover the area's waterfalls.

Berkshire East Ski Resort

Hawley Hotel Deals

Secluded Family Getaway w/ On-Site Creek in Hawley

Secluded Family Getaway w/ On-Site Creek in Hawley

2 out of 5
Hawley Massachusetts
10/10 Exceptional! (2 reviews)
The house was a perfect space for my family for a ski weekend! It was comfortable for adults and our small children. The host was very easy to work with and the house had everything we needed. We will definitely make a return trip!

Reviewed on Jan 25, 2026

Get rates
Secluded Family Getaway w/ On-Site Creek in Hawley
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
$128 nightly
The price is $143 total per night from Mar 31 to Apr 1
$143 total
Mar 31 - Apr 1
Total with taxes and fees
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
$121 nightly
The price is $136 total per night from Apr 2 to Apr 3
$136 total
Apr 2 - Apr 3
Total with taxes and fees
9/10 Wonderful! (866 reviews)
Love it here. We stay a few times a year and are actually local to the hotel. Just a relaxed experience.

Reviewed on Mar 1, 2026

Berkshire Mountain Lodge
See all 770 properties in Hawley
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 Hawley Vacation Packages

Hawley Essential Information

Language
English
Currency
U.S dollars
Population
340
Top Sights
Bissell Covered Bridge, Hawley Bog Preserve and Charlemont Federated Church

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Frequently asked questions

How much does a Hawley vacation package cost?
You'll find cheap prices from $343 on Expedia for your Hawley getaway. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Hawley costs.
What are the cheapest months to go to Hawley?
If you're looking to book a cheap Hawley vacation package, consider traveling in November, December and January. You'll usually find lower prices on airfares and hotels during these quieter months — perfect for a budget-friendly getaway.
How many days is enough for Hawley?
The ideal duration for your Hawley vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you enough time to visit all the top attractions and discover some hidden gems along the way.
How to find the best Hawley package deals?
Finding a cheap Hawley package deal is easy with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most affordable Hawley package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Hawley vacation as a package?
You can enjoy significant savings on your Hawley retreat by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Hawley?
Score amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Hawley escape.
Does Expedia offer Book Now, Pay Later Hawley vacation packages?
If you're anything like us, you love discovering new places but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Hawley break over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.