Sharon Vacations from $793

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The Latest Sharon vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Save 100% on your flight
Price was $1,011, price is now $793 per person
$793
per person
Dec 25 - Dec 31
just found
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
7/10 Good! (1,003 reviews)

The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Save 100% on your flight
Price was $3,576, price is now $2,620 per person
$2,620
per person
Dec 25 - Dec 31
just found
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
No reviews

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,205, price is now $922 per person
$922
per person
Dec 25 - Dec 31
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
9/10 Wonderful! (890 reviews)

Mountain Green Resort

Mountain Green Resort

4 out of 5
Save 100% on your flight
Price was $3,732, price is now $2,912 per person
$2,912
per person
Dec 25 - Dec 31
just found
Roundtrip flight included
Boston (BOS) to Rutland (RUT)
4/10 (2 reviews)
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.

Reviewed on Jan 28, 2026

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $2,085, price is now $1,682 per person
$1,682
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.8/10 Excellent! (1,002 reviews)
The manager and owners do not help with any situation. My room was not clean. Pubic hairs in the shower. Hairs all over the floor, spiders, crumbs all over the valet. Baseboards were covered in filth. No one would return my calls, emails or text messages.

Reviewed on Oct 30, 2026

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Stay near popular Sharon attractions

White River Wildlife Management Area

This undisturbed wilderness offers diverse habitats from steep forests to river bottomlands, home to abundant wildlife. Explore maple-hemlock forests while spotting deer, otters, and salmon in their natural environment.
See properties

Sharon Hotel Deals

Fireside Inn & Suites West Lebanon

Fireside Inn & Suites West Lebanon

2.5 out of 5
25 Airport Road West Lebanon NH
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $129 total per night from Nov 23 to Nov 24
$129 total
Nov 23 - Nov 24
Total with taxes and fees
Fireside Inn & Suites West Lebanon
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
$156 nightly
The price is $172 total per night from Nov 5 to Nov 6
$172 total
Nov 5 - Nov 6
Total with taxes and fees
The Mountain Inn at Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
9.4/10 Exceptional! (628 reviews)
"Absolutely beautiful hotel and property, which is a destination just in and of itself. Very comfortable, great dining options, gorgeous spa, and very walkable, if you decide to wander; Woodstock is a town right out of a Hallmark movie, after all."

Reviewed on Oct 28, 2026

Woodstock Inn & Resort
See all 1,776 properties in Sharon
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 Sharon Vacation Packages

Sharon Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Top Sights
Saskadena Six Ski Area, Montshire Museum of Science and Woodstock Town Hall Theatre

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Frequently asked questions

How much does a Sharon vacation package cost?
Offering excellent value package deals from $793 on Expedia, you'll be surprised at how little a vacation to Sharon costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Sharon?
March, May and October are the best times to search for cheap Sharon vacation packages. Choosing to travel in less busy months means you can usually find lower prices on accommodations and flights.
How many days is enough for Sharon?
With a well-organized schedule, you can easily hit the top Sharon sights in a handful of days. But if you prefer to discover hidden gems or go on day trips, consider booking your Sharon vacation for longer.
How to find the best Sharon package deals?
Use Expedia's handy filters to find some fabulous Sharon package deals. When you start your search, simply 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 look for Sharon package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Sharon vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually land a better deal than booking each component separately. And you'll still get the freedom to create a personalized Sharon vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Sharon?
Secure incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Sharon vacation.
Does Expedia offer Book Now, Pay Later Sharon vacation packages?
Your Sharon getaway is meant to be an escape from your busy life, not a source of money-related stress. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

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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.