South Woodstock Vacation Packages 2026/2026 from $1,058

South Woodstock flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Chalet 239

$1,058

per person

Feb 9 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Richmond (RIC) to Springfield (VSF)

The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.

Jackson Gore Village

Jackson Gore Base Area

Save 100% on your flight

$2,515

per person

Feb 9 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Richmond (RIC) to Springfield (VSF)

Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.

Stone Hearth Inn and Eatery

Save 100% on your flight

$1,333

per person

Feb 9 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Richmond (RIC) to Springfield (VSF)

This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free buffet breakfast each morning. A garden is also provided.

Mountain Green Resort

Save 100% on your flight

$1,380

per person

Jan 15 - Jan 19

found 9 hours ago

Roundtrip non-stop flight included

New York (JFK) to Rutland (RUT)

An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.

Mount Snow Grand Summit Resort

Save 100% on your flight

$2,160

per person

Feb 9 - Feb 16

found 1 day ago

Roundtrip non-stop flight included

Richmond (RIC) to Springfield (VSF)

Ski-in/ski-out access, a full-service spa, and 2 hot tubs are all featured at this smoke-free resort. Enjoy a meal from the restaurant and freebies like WiFi in public areas and an area shuttle. You'll appreciate the outdoor pool, bar/lounge, and laundry facilities.

Top South Woodstock hotels deals

Kedron Valley Inn

4778 South Road South Woodstock VT

$220 nightly

$242 total

Dec 10 - Dec 11

Total with taxes and fees

A restaurant and a bar/lounge are featured at this inn. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace is also provided.

Pet friendly

Parking included

White River Inn and Suites

91 Ballardvale Drive White River Junction VT

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$133 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. There's an indoor pool on site, and a 24-hour front desk and a terrace are also provided.

Pool

Breakfast included

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$163 nightly

$179 total

Dec 14 - Dec 15

Total with taxes and fees

This hotel features a 24-hour gym and a hot tub. There's a free ski shuttle, and ski passes and ski storage are available on site. WiFi in public areas is free.

Hot Tub

Pet friendly

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$379 nightly

$417 total

Dec 16 - Dec 17

Total with taxes and fees

This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.

Pool

Hot Tub

The Mountain Inn at Killington

47 Old Mill Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$167 nightly

$184 total

Dec 10 - Dec 11

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the free ski shuttle and onsite ski storage. Enjoy the gym and free perks like continental breakfast and free self parking.

Pool

Breakfast included

Align Inn Vermont

5817 Woodstock Rd Quechee VT

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$138 total

Jan 8 - Jan 9, 2026

Total with taxes and fees

This hotel features an indoor pool and a gym. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

Pool

Breakfast included

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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 are vacation packages to South Woodstock?

Starting from as little as $1,058, hotel and flight packages are a fabulous way to stretch your vacation budget. Watch out South Woodstock — here you come!

How long should my South Woodstock vacation be?

There aren't any hard and fast rules for how long you should spend in South Woodstock, but many travelers stay around 3 nights. Got some wiggle room in your departure date? Extend your escape by another night or two. Then you'll have plenty of time to check out the area's off-the-beaten-path gems as well.

Where can I get the best vacation package deals for South Woodstock?

One word — Travelocity. With no less than 400 partner airlines and 1,000,000 properties across the globe, it's easy to put together a South Woodstock package deal that suits your travel style.

Why should I purchase my South Woodstock vacation bundle via Travelocity?

With top-notch service, 24/7 support and some of the most amazing getaways around, you'll never roam alone. And if you find a better price, we'll match it. That's our Price Match Guarantee.

Can I save on my South Woodstock car rental if I combine it with my hotel or flight?

Bundling your flight, car and hotel into a South Woodstock vacation package is a great way to land the best deal. Plus, having your own rental car gives you the freedom to get to all the landmarks you want to explore. Sitting 110 mi away from South Woodstock, Fenway Park is one attraction that should be on your agenda. Fill up the tank and make a day trip of it.

Which airport is best for South Woodstock?

Lebanon Municipal Airport (LEB), 12 mi east of the city center, is where many people start their adventures in South Woodstock. But Rutland Southern Vermont Regional Airport (RUT) (20 mi away from central South Woodstock) could suit you better.

Where should I stay when visiting South Woodstock?

The Kedron Valley Inn is the number one choice of many visitors. Book now before it's too late.