Shaftsbury Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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Top hotels in Shaftsbury
The Williams Inn
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
S$365
14 Sept - 15 Sept
includes taxes & fees
Hotel Vervana, Trademark Collection by Wyndham
141 West Main Street Bennington VT
Fully refundableReserve now, pay when you stay
S$152
13 Sept - 14 Sept
includes taxes & fees
8.2/10 Very good! (1,000 reviews)
"Location and price"
Reviewed on 25 Aug, 2026
Kimpton Taconic Hotel by IHG
3835 Main St. Manchester VT
Fully refundable
S$359
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (863 reviews)
"Very nice hotel off main road in and out of Manchester. Great outdoor porches to sit and relax. Free beverage coupons at social hour with free popcorn and pretzels. Staff friendly. Rooms very nice, spacious and beds very comfortable. Room temps were great. Free coffee in lobby area, free easy parking. ..."
Reviewed on 26 Aug, 2026
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.
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 studying the exhibits at Robert Frost Stone House Museum in South Shaftsbury. Discover the mountain views and cafes 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 exploring the galleries in Shaftsbury Historical Society Museum during your travels in Shaftsbury. Discover the mountain views and cafes in this relaxing area.
Frequently asked questions
How much does a Shaftsbury holiday package cost?
You can grab a holiday package to this popular destination on Expedia. However, how much your holiday to Shaftsbury costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Shaftsbury?
To score cheap Shaftsbury holiday packages, organise your getaway outside of busy periods such as public holidays. You'll generally find lower prices and better availability for hotels and flights.
How many days is enough for Shaftsbury?
For your Shaftsbury holiday, a few days will be enough to tour the top spots. Make sure to stop by Robert Frost Stone House Museum — it's one of the major attractions in this destination. If you're looking for more adventure, consider basing yourself here and heading off on some day trips from Shaftsbury.
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 travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Shaftsbury holiday as a package?
Expedia holiday 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 customised Shaftsbury holiday by choosing your preferred airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Shaftsbury?
- Choose your dates: What you plan to do in Shaftsbury and your favourite season can help you decide when to get away.
- Calculate your budget: Make sure you have enough money to pay for everything from transportation and meals to flights and experiences. Your accommodation will likely be the biggest expense during your trip to Shaftsbury.
- Decide your trip length: Consider how long you'd like to spend exploring Shaftsbury. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
- Bundle your airfare and accommodation: After you've nailed down your dates and duration, book the right Shaftsbury holiday package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
