Shaftsbury Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Hannie

Top hotels in Shaftsbury

Hotel Downstreet, Ascend Hotel Collection
Hotel Downstreet, Ascend Hotel Collection
3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is 3.756.304 ₫ per night from 27 Jul to 28 Jul
3.756.304 ₫
4.195.792 ₫ total
27 Jul - 28 Jul
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Staff super friendly, most comfortable beds imo I’ve slept in. I sleep better there then at my house."

Reviewed on 18 Jun 2025

Hotel Downstreet, Ascend Hotel Collection
The Equinox Golf Resort & Spa
The Equinox Golf Resort & Spa
4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is 3.707.601 ₫ per night from 8 Jul to 9 Jul
3.707.601 ₫
5.507.107 ₫ total
8 Jul - 9 Jul
includes taxes & fees
7.2/10 Good! (485 reviews)
"I had a wonderful time and did Rhumba for the first time in the pool! Lovely walk to the pond also!"

Reviewed on 23 Jun 2025

The Equinox Golf Resort & Spa
The Williams Inn
The Williams Inn
4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is 6.464.033 ₫ per night from 9 Jul to 10 Jul
6.464.033 ₫
7.220.325 ₫ total
9 Jul - 10 Jul
includes taxes & fees
9.6/10 Exceptional! (457 reviews)
"great!"

Reviewed on 20 Jun 2025

The Williams Inn
See all 1,995 properties in Shaftsbury
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.

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?

  1. Choose your dates: What you plan to do in Shaftsbury and your favourite season can help you decide when to get away.
  2. 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.
  3. 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.
  4. Bundle your airfare and accommodation: After you've nailed down your dates and duration, book the right Shaftsbury holiday package for you.

Popular places to visit

Lake Shaftsbury State Park

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.

Lake Shaftsbury State Park

Robert Frost Stone House Museum

You can spend time studying the exhibits at Robert Frost Stone House Museum in South Shaftsbury. Discover the mountain views and cafes in this relaxing area.

Robert Frost Stone House Museum

Howard Park

Explore the great outdoors at Howard Park, a lovely green space in Shaftsbury. Attend a sporting event or discover the mountain views in this trendy area.

Howard Park