South Woodstock Vacation Packages 2026 from $786

South Woodstock flight + hotel vacation packages

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

My Place Hotel-Randolph VT

$786

per person

Oct 20 - Oct 22

found 23 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Rutland (RUT)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A grocery/convenience store, a computer station, and laundry facilities are also on offer.

The Shire Woodstock

$1,103

per person

Oct 20 - Oct 22

found 23 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) 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.

Lake Bomoseen Lodge

$814

per person

Oct 20 - Oct 22

found 23 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Rutland (RUT)

A private beach and a restaurant are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking. There's a bar/lounge on site, and a terrace and barbecue grills are also provided.

The Mountain Top Inn & Resort

$942

per person

Oct 20 - Oct 22

found 23 hours ago

Roundtrip non-stop flight included

Cleveland (CLE) to Rutland (RUT)

This resort features a private beach, ski-in/ski-out access, and a restaurant. Enjoy a day at the beach kayaking, or relax with sun loungers. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls.

Top South Woodstock hotels deals

Kedron Valley Inn

4778 South Road South Woodstock VT

$410 nightly

$451 total

Sep 15 - Sep 16

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

Align Inn Vermont

5817 Woodstock Rd Quechee VT

$105 nightly

$116 total

Sep 13 - Sep 14

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

Fireside Inn & Suites West Lebanon

25 Airport Road West Lebanon NH

Free Cancellation

Reserve now, pay when you stay

$173 nightly

$187 total

Sep 13 - Sep 14

Total with taxes and fees

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

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

Sep 13 - Sep 14

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

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$589 nightly

$648 total

Sep 14 - Sep 15

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

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$165 nightly

$181 total

Sep 13 - Sep 14

Total with taxes and fees

This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Self parking, a terrace, and a lobby fireplace are also offered.

Hot Tub

Pet friendly

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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 $786, 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.