South Shaftsbury Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in South 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 €146 per night from 24 Aug to 25 Aug
€146
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (1,007 reviews)
"Great stay. Well balanced, clean, friendly."

Reviewed on 20 Aug 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 €173 per night from 1 Sept to 2 Sept
€173
1 Sept - 2 Sept
includes taxes & fees
7.2/10 Good! (514 reviews)
"Classic colonial inn. Beautiful property in a nice area with good amenities. Golf course is nice. Scenic and challenging design."

Reviewed on 20 Aug 2025

The Equinox Golf Resort & Spa
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
The price is €224 per night from 7 Sept to 8 Sept
€224
7 Sept - 8 Sept
includes taxes & fees
9.6/10 Exceptional! (486 reviews)
"Clean"

Reviewed on 18 Aug 2025

The Williams Inn
See all 1,393 properties in South 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 South Shaftsbury holiday package cost?
You'll find cheap prices on Expedia for your South Shaftsbury escape. However, a range of factors like the season, choice of hotel and length of stay will influence how much your holiday to South Shaftsbury costs.
What are the cheapest months to go to South Shaftsbury?
You can generally find lower prices and better availability in January, February and March. Explore our cheap South Shaftsbury holiday packages and you could score some great off-season discounts.
How many days is enough for South Shaftsbury?
The ideal duration of your South Shaftsbury holiday depends on what you'd like to see. Typically, a handful of days to a week will give you enough time to go to all the major attractions and explore some hidden treasures along the way.
How to find the best South Shaftsbury package deals?
Use Expedia's filter tool to help you find some great South Shaftsbury package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for South Shaftsbury package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book a South Shaftsbury holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still have the freedom to create a customised South Shaftsbury holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to South Shaftsbury?
If you're considering a spontaneous South Shaftsbury getaway, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can score terrific deals on your hotels and flights by booking ahead.
How to plan a trip to South Shaftsbury?

  1. Choose when to get away: Check your calendar and get packing. Your preferred season and the activities on offer will also help you decide when to escape to South Shaftsbury.
  2. Budget wisely: In addition to the price of your stay, you should consider other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that may come up during your trip to South Shaftsbury.
  3. Decide your trip length: Think about how much time you'd like to spend discovering South Shaftsbury. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your airfare and accommodation: After you've nailed down your dates and duration, book the ideal South 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.