Shaftsbury Vacations from $471
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Your Shaftsbury Vacation
Our vacation packages to Shaftsbury give you the power to customize your own adventure. Tailor your getaway to suit your interests and needs and make the most of your time in this fantastic city. Fill up your itinerary with visits to Sugar Shack, Lake Shaftsbury State Park and Park McCullough House, some of the attractions you shouldn't miss during your trip to Shaftsbury. Check out Expedia's extensive range of travel options and begin planning your ideal vacation to Shaftsbury today.
The Latest Shaftsbury vacation packages
Price found within the past 48 hours. Click for updated prices.
Lodges At Cresthaven
$471
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.4/10 Exceptional! (628 reviews)
They have pocket doors on the bathrooms with no locks. The slope of the property was so great that my reasonably healthy wife could not access the beach area. The property is beautiful, but in my opinion it is not well suited for older adults.
Reviewed on Aug 27, 2026
The Cornell Inn, Lenox & The Berkshires
$1,202
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
9.2/10 Wonderful! (1,007 reviews)
Lovely people and place. Breakfast was great and so was the room. Highly recommend.
Reviewed on Aug 31, 2026
Stay near popular Shaftsbury attractions
Lake Shaftsbury State Park
10.0/10 (1 review)
Commune with nature and explore the great outdoors at Lake Shaftsbury State Park during your travels in Shaftsbury. Visit the spas or attend a sporting event in this quaint area.
Robert Frost Stone House Museum
9.0/10 (12 reviews)
You can spend time browsing the exhibits at Robert Frost Stone House Museum during your trip to South Shaftsbury. Discover the mountain views and coffeehouses in this trendy area.
Howard Park
10.0/10 (1 review)
Explore the great outdoors at Howard Park, a lovely green space in Shaftsbury. Attend a sporting event or discover the mountain views in this relaxing area.
Maple Hill
Commune with nature and explore the great outdoors at Maple Hill during your travels in Shaftsbury. Wander the parks or discover the area's mountain views.
Shaftsbury Historical Society Museum
You can spend an afternoon browsing the exhibits at Shaftsbury Historical Society Museum during your trip to Shaftsbury. Discover the mountain views and coffeehouses in this relaxing area.
Shaftsbury Hotel Deals
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
Fully refundable
$148 nightly
$165 total
Oct 1 - Oct 2
Total with taxes and fees
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$263 nightly
$293 total
Sep 14 - Sep 15
Total with taxes and fees
9.6/10 Exceptional! (663 reviews)
"Great place. Would love to have a swimming pool for lap swimming"
Reviewed on Aug 31, 2026
Grand Summit Resort, A Vail Resorts Property
89 Grand Summit Way West Dover VT
Fully refundable
$169 nightly
$186 total
Sep 29 - Sep 30
Total with taxes and fees
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 Shaftsbury Vacation Packages
Shaftsbury Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Lake Shaftsbury State Park, Prospect Mountain Cross-Country Ski Center and Woodford State Park |
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Frequently asked questions
How much does a Shaftsbury vacation package cost?
You can grab a vacation package to this popular destination from $471 on Expedia. However, how much your vacation to Shaftsbury costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Shaftsbury?
If you're looking to score a cheap Shaftsbury vacation package, consider planning a trip in March, April and November. You'll generally find better rates on airfares and hotels during these quieter months — perfect for a budget-friendly break.
How many days is enough for Shaftsbury?
With a well-planned itinerary, you can easily tick off the most popular Shaftsbury sights in a handful of days. But if you prefer to discover hidden spots or take day trips, consider booking your Shaftsbury vacation for longer.
How to find the best Shaftsbury package deals?
Landing a cheap Shaftsbury package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget, apply 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 view the most pocket-friendly Shaftsbury package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Shaftsbury vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still get the freedom to create a customized Shaftsbury vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Shaftsbury?
If you're considering a spur-of-the-moment Shaftsbury trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Shaftsbury vacation packages?
Set off on your perfect escape to Shaftsbury with Expedia's Book Now, Pay Later vacations. No need to save up or wait until your next paycheck — we've partnered with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, you can easily stick to your budget and snap up cheap deals before they disappear.
Explore a world of travel with Expedia
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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.
