South Shaftsbury Vacations

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Find the Best South Shaftsbury Vacation Packages

South Shaftsbury Hotel Deals

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Shaftsbury VT
10/10 Exceptional! (240 reviews)
"It was a great weekend away, enjoying the coziness of the rustic barn house and the quietness of the country feel. Definitely would consider returning again and spending more time visiting the surrounding areas. The host was spot on and very much easy to communicate with which always makes the process ..."

Reviewed on 28 June 2026

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Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is AEDĀ 590 per night from Aug 18 to Aug 19
AEDĀ 590
AEDĀ 659 total
18 Aug - 19 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"This was a beautiful hotel close to the best part of North Adams. The gallery on the lobby floor gives it an upscale vibe but without too high a price tag. It was very convenient for our college visit to Williams College. It was very quiet even directly across from the elevator. The beds were very ..."

Reviewed on 17 July 2026

Hotel Downstreet, an Ascend Collection Hotel
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham VT
The price is AEDĀ 1,825 per night from Aug 19 to Aug 20
AEDĀ 1,825
AEDĀ 3,135 total
19 Aug - 20 Aug
includes taxes & fees
9.8/10 Exceptional! (6 reviews)
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."

Reviewed on 25 May 2026

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
See all 1,506 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.

Stay near popular South Shaftsbury attractions

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 relaxing area.
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Frequently asked questions

How much does a South Shaftsbury vacation package cost?
You'll find cheap prices on Expedia for your South Shaftsbury escape. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to South Shaftsbury costs.
What are the cheapest months to go to South Shaftsbury?
January, February and March are the best times to look for cheap South Shaftsbury vacation packages. Traveling in quieter periods means you can typically find better prices on flights and accommodations.
How to find the best South Shaftsbury package deals?
Finding a cheap South Shaftsbury package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can fine-tune your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most pocket-friendly South Shaftsbury package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a South Shaftsbury vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging hotels and flights separately. Better still, you can personalize your South Shaftsbury escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to South Shaftsbury?
If you've got your South Shaftsbury vacation dates locked in, book as early as you can to bag some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for traveling on a whim.
How to plan a trip to South Shaftsbury?

  1. Pick the best time to travel: Your schedule, favorite season and the type of weather you like can all influence your decision on when to visit South Shaftsbury.
  2. Plan your budget wisely: On top of the price of your accommodations, you should factor in other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that may arise during your trip to South Shaftsbury.
  3. Decide how long to go for: Now that you're more familiar with South Shaftsbury, you can figure out the ideal length of your break. Pull together a draft plan and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a tailored South Shaftsbury vacation package.