Hawley Vacations from $382

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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.
enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Save 100% on your flight
Price was $532, price is now $382 per person
$382
per person
Mar 27 - Mar 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
Front desk staff was amazing. Room could have been cleaner. Comfortable bed. Room could have used a microwave.

Reviewed on Feb 1, 2026

D. Hotel Suites & Spa

D. Hotel Suites & Spa

3 out of 5
Save 100% on your flight
Price was $776, price is now $467 per person
$467
per person
Mar 18 - Mar 24
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Boston (BOS)
9.4/10 Exceptional! (2,242 reviews)
Clean, cozy on a very cold night! Breakfast had a good variety and staff was pleasant. Will definitely go back

Reviewed on Jan 31, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $896, price is now $594 per person
$594
per person
Mar 6 - Mar 8
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) 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

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Save 100% on your flight
Price was $1,005, price is now $670 per person
$670
per person
Mar 14 - Mar 17
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
Room very well appointed and gym was the stand out

Reviewed on Jan 25, 2026

Revere Hotel Boston Common

Revere Hotel Boston Common

4 out of 5
Bay Village
Save 100% on your flight
Price was $666, price is now $450 per person
$450
per person
Apr 6 - Apr 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Boston (BOS)
9/10 Wonderful! (1,891 reviews)
Spotless and perfect balcony

Reviewed on Jan 31, 2026

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Discover the most popular places to visit in Hawley

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
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

Berkshire East Ski Resort

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! (1 review)
Everything about this house is ideal! The rooms are meticulously crafted. Two wood stoves to keep it cozy and books everywhere! The common space is large enough for everyone to gather for food and drinks and spending time together, but there are also sitting nooks throughout that you could have some ...

Reviewed on Nov 21, 2025

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
$126 nightly
The price is $141 total per night from Feb 22 to Feb 23
$141 total
Feb 22 - Feb 23
Total with taxes and fees
8.6/10 Excellent! (2,219 reviews)
Everything was great, the staff, the room, and the amenities. We will be coming back.

Reviewed on Jan 25, 2026

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 Mar 2 to Mar 3
$136 total
Mar 2 - Mar 3
Total with taxes and fees
9/10 Wonderful! (821 reviews)
Friendly informed staff, super clean room, the hot chocolate machine !!!!!

Reviewed on Jan 27, 2026

Berkshire Mountain Lodge
See all 784 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 $382 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.