Shaftsbury Vacations from $545

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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.
The Dewey

The Dewey

3.5 out of 5
Price was $716, price is now $545 per person
$545
per person
Apr 8 - Apr 11
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.6/10 Excellent! (329 reviews)
Great spot. Lots of history.

Reviewed on Sep 12, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was $1,063, price is now $718 per person
$718
per person
Apr 8 - Apr 11
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.4/10 Exceptional! (13 reviews)
Wow, just wow! My high school friend and I met up at Prospect Berkshires for a girls weekend. We had an incredible time relaxing by using all the amenities. The staff are so helpful and profession.

Reviewed on Nov 29, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Manchester Village Historic District
Save 100% on your flight
Price was $2,412, price is now $1,774 per person
$1,774
per person
Feb 13 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Albany (ALB)
7.4/10 Good! (567 reviews)
Was surprised at the dirty floors in common area and in my room one of the curtain sheers was ripped, other curtains were hanging off hokks, caulking at sink looked old, cracked, carpets in staircase dirty. I fear this beautiful hotel is in a downward spiral. One front desk person directed me to closed restaurants...

Reviewed on Jan 9, 2026

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

3.5 out of 5
Price was $830, price is now $627 per person
$627
per person
Apr 8 - Apr 11
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9/10 Wonderful! (1,002 reviews)
The staff was very welcoming and attentive. Room was clean.

Reviewed on Jan 3, 2026

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Price was $810, price is now $617 per person
$617
per person
Apr 8 - Apr 11
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
9.8/10 Exceptional! (38 reviews)
It was a very pleasant hybrid of a classic BnB with the privacy of an air BnB. Host was on point and communicative. We loved hanging out downstairs in the living room(s). Breakfast was fabulous

Reviewed on Jan 14, 2026

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Discover the most popular places to visit in Shaftsbury

Lake Shaftsbury State Park

5/5(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.

Lake Shaftsbury State Park

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 trendy area.

Shaftsbury Historical Society 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

Shaftsbury Hotel Deals

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
$125 nightly
The price is $140 total per night from Feb 2 to Feb 3
$140 total
Feb 2 - Feb 3
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
friendly accommodating staff

Reviewed on Jan 1, 2026

Hotel Downstreet, an Ascend Collection Hotel
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street Williamstown MA
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $208 total per night from Jan 25 to Jan 26
$208 total
Jan 25 - Jan 26
Total with taxes and fees
9.6/10 Exceptional! (560 reviews)
General ambience is lovely.

Reviewed on Jan 8, 2026

The Williams Inn
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
$249 nightly
The price is $273 total per night from Jan 26 to Jan 27
$273 total
Jan 26 - Jan 27
Total with taxes and fees
7.2/10 Good! (585 reviews)
Was surprised at the dirty floors in common area and in my room one of the curtain sheers was ripped, other curtains were hanging off hokks, caulking at sink looked old, cracked, carpets in staircase dirty. I fear this beautiful hotel is in a downward spiral. One front desk person directed me to ...

Reviewed on Jan 9, 2026

The Equinox Golf Resort & Spa
See all 2,124 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.

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 $545 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.

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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.