South Woodstock Vacation Packages 2025/2026 from $548

South Woodstock flight + hotel vacation packages

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

Sinclair Inn Bed and Breakfast

$548

per person

Jan 22 - Jan 25

found 1 day ago

Roundtrip non-stop flight included

Miami (MIA) to Springfield (VSF)

This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast and free WiFi. A garden and a picnic area are also provided.

Killington Mountain Lodge, Tapestry Collection by Hilton

Save 100% on your flight

$1,145

per person

Dec 28 - Jan 1

found 1 day ago

Roundtrip flight included

Miami (MIA) to Rutland (RUT)

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.

The Shire Woodstock

$860

per person

Dec 28 - Jan 1

found 1 day ago

Roundtrip flight included

Miami (MIA) to Springfield (VSF)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.

North Star Lodge and Resort

$804

per person

Dec 28 - Jan 1

found 1 day ago

Roundtrip flight included

Miami (MIA) to Rutland (RUT)

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Families will appreciate the arcade/game room and onsite laundry facilities. Enjoy the gym and perks like free self parking and free WiFi.

Top South Woodstock hotels deals

Kedron Valley Inn

4778 South Road, South Woodstock, VT

$259 nightly

$285 total

Nov 10 - Nov 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

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd, Killington, VT

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$143 total

Nov 16 - Nov 17

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

Comfort Inn Rutland - Killington

19 Allen St, Rutland, VT

Free Cancellation

Reserve now, pay when you stay

$110 nightly

$121 total

Nov 13 - Nov 14

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and free perks like continental breakfast and free self parking.

Pool

Hot Tub

Woodstock Inn & Resort

Fourteen The Green, Woodstock, VT

$369 nightly

$406 total

Nov 30 - Dec 1

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

White River Inn and Suites

91 Ballardvale Drive, White River Junction, VT

Free Cancellation

Reserve now, pay when you stay

$121 nightly

$133 total

Nov 10 - Nov 11

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

The Shire Woodstock

46 Pleasant St., Woodstock, VT

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$152 total

Nov 11 - Nov 12

Total with taxes and fees

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.

Pet friendly

Parking 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 $548, 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.