Williamstown Vacations from $523

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Your Williamstown Vacation

Our vacation packages to Williamstown give you the power to create your own adventure. Tailor your journey to suit your interests and needs and make the most of your time in this fabulous city. Every trip to Williamstown needs a well-crafted itinerary. Fill yours with major attractions like Williams College, Massachusetts Museum of Contemporary Art and Mount Greylock. Your dream Williamstown vacation is just clicks away. Search airfares, hotels and more on Expedia for an adventure that's tailored just for you.

The Latest Williamstown vacation packages

Price found within the past 48 hours. Click for updated prices.
Gedney Farm

Gedney Farm

3.5 out of 5
Save 100% on your flight
Price was $759, price is now $523 per person
$523
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.4/10 Exceptional! (132 reviews)
My wife and I chose Gedney Farms at the last minute to enjoy a quick escape from the city. The staff was friendly and welcoming. The checkin and checkout experience was seamless. The room had a truly rustic charm, and clean and orderly. In the morning we took a nice walk on the grounds. For a quick and relaxing getaway, Gedney Farms is a great choice.

Reviewed on Nov 2, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,723, price is now $1,026 per person
$1,026
per person
Dec 28 - Jan 2
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.8/10 Exceptional! (13 reviews)
Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay....

Reviewed on Oct 20, 2025

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $1,303, price is now $824 per person
$824
per person
Dec 28 - Jan 2
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.4/10 Exceptional! (110 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Save 100% on your flight
Price was $1,141, price is now $769 per person
$769
per person
Dec 28 - Jan 2
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
17.6/10 Exceptional! (3 reviews)
The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open

Reviewed on Nov 12, 2025

Church Des Artistes Guest House

Church Des Artistes Guest House

3 out of 5
Roundout
Save 100% on your flight
Price was $5,233, price is now $3,586 per person
$3,586
per person
Dec 28 - Jan 2
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
18.8/10 Exceptional! (18 reviews)
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Discover the most popular places to visit in Williamstown

Williams College

Take a campus tour or just explore the area of Williams College, during your travels in Williamstown. In the area, take in the fascinating museums and mountain views.

Williams College

The Clark Art Institute

You can spend an afternoon exploring the galleries in The Clark Art Institute during your trip to Williamstown. In the area, take in the fascinating museums and mountain views.

The Clark Art Institute

Williamstown Theatre Festival

You can enjoy a show at Williamstown Theatre Festival on your trip to Williamstown. Discover the mountain views in this family-friendly area, or enjoy its ski slopes.

Williamstown Theatre Festival

Williamstown 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
$94 nightly
The price is $105 total per night from Nov 23 to Nov 24
$105 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (2,135 reviews)
My room was amazing nice view of the mountains the staff were very friendly they have a beautiful indoor pool amazing hot tub and cute movie theater along with a game room and other activities

Reviewed on Nov 17, 2025

Vacation Village in the Berkshires
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $208 total per night from Nov 23 to Nov 24
$208 total
Nov 23 - Nov 24
Total with taxes and fees
9.6/10 Exceptional! (540 reviews)
Clean,heating was noisy,bed was to soft,shower head dripped. Very friendly and helpful staff.good breakfast!

Reviewed on Nov 14, 2025

The Williams Inn
Huttopia Berkshires

Huttopia Berkshires

1 out of 5
312 Kittle Rd Williamstown MA
$189 nightly
The price is $211 total per night from Dec 14 to Dec 15
$211 total
Dec 14 - Dec 15
Total with taxes and fees
10/10 Exceptional! (7 reviews)
Healthy food too!

Reviewed on Oct 20, 2025

Huttopia Berkshires
See all 1,247 properties in Williamstown
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 Williamstown Vacation Packages

Williamstown Essential Information

Language
English
Currency
U.S dollars
Population
4,300
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Jiminy Peak Mountain Resort, Natural Bridge State Park and Williamstown Theatre Festival

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Frequently asked questions

How much does a Williamstown vacation package cost?
You'll find cheap prices from $523 on Expedia for your Williamstown break. However, factors like the season, length of stay and your choice of hotel will determine how much your vacation to Williamstown costs.
What are the cheapest months to go to Williamstown?
You're likely to find lower rates and greater availability in January, October and December. Check out our cheap Williamstown vacation packages and you could score some great off-season discounts.
How many days is enough for Williamstown?
With a well-organized itinerary, you can easily visit the top Williamstown sights in a handful of days. But if you prefer to explore off the beaten track or go on day trips, think about booking your Williamstown vacation for longer.
Is it worth booking a vacation package to Williamstown?
Williamstown is a good vacation destination with attractions like The Clark Art Institute among the many things to keep you busy. Whether you're heading away with the family or planning a trip with friends, a Williamstown vacation promises fun for everyone.
How to find the best Williamstown package deals?
Bagging a cheap Williamstown package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most economical Williamstown package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Williamstown vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and hotels individually. Better still, you can customize your Williamstown escape to fit your exact style. 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 Williamstown?
Score fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Williamstown escape.
How to plan a trip to Williamstown?

  1. Choose your travel dates: What you plan to do in Williamstown and your favorite season will help you decide when to go.
  2. Set a budget: Consider costs like flights, food and transportation when working out how much to set aside for your trip to Williamstown. Then, pick a hotel that works with your budget, whether that's an economical stay or a more luxurious retreat.
  3. Organize your Williamstown getaway with Expedia's trip planning tool: Look for and book stays and experiences all in one place. You can also collaborate with family and friends to plan an unforgettable trip to Williamstown together.
  4. Decide your trip length: Consider how long you want to spend discovering Williamstown. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  5. Bundle your accommodations and airfare: After you've settled on your trip dates and duration, lock in the ideal Williamstown vacation package for you.
  6. Add on excursions and experiences: Take a look at our dedicated travel guide to find some awesome things to do in Williamstown. Book tickets or make reservations in advance to save time and avoid the hassle of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Williamstown vacation packages?
Secure your dream trip to Williamstown with Expedia's Book Now, Pay Later vacations. No need to save like crazy or wait until your next paycheck — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can split the cost across 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to budget for your trip and snap up cheap deals while they last.

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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.