South Woodstock Vacation Packages 2026 from $539

South Woodstock flight + hotel vacation packages

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

Chalet 239

$539

per person

Jul 26 - Jul 30

found 5 hours ago

Roundtrip non-stop flight included

Tampa (TPA) 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.

The Quechee Inn at Marshland Farm

$602

per person

Jul 26 - Jul 30

found 5 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Rutland (RUT)

A restaurant and a bar/lounge are featured at this hotel. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. A terrace, a garden, and a lobby fireplace are also on offer.

Latchis Hotel

$591

per person

Jul 26 - Jul 30

found 5 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Springfield (VSF)

A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.

Harvest Barn Inn

$650

per person

Jul 26 - Jul 30

found 5 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Rutland (RUT)

This bed & breakfast features free WiFi in public areas, concierge services, and free self parking. Enjoy the free full breakfast each morning. A terrace is also provided.

Bentley House Bed and Breakfast

$575

per person

Jul 26 - Jul 30

found 5 hours ago

Roundtrip non-stop flight included

Tampa (TPA) to Rutland (RUT)

This bed & breakfast doesn't skimp on freebies - guests receive free breakfast, free WiFi, and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A lobby fireplace, a communal living room, and luggage storage are also on offer.

Top South Woodstock hotels deals

Kedron Valley Inn

4778 South Road South Woodstock VT

$267 nightly

$294 total

Jun 4 - Jun 5

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

Fireside Inn & Suites West Lebanon

25 Airport Road West Lebanon NH

Free Cancellation

Reserve now, pay when you stay

$140 nightly

$152 total

May 31 - Jun 1

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

Killington Mountain Lodge, Tapestry Collection by Hilton

2617 Killington Rd Killington VT

Free Cancellation

Reserve now, pay when you stay

$130 nightly

$143 total

May 25 - May 26

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

Comfort Inn Rutland - Killington

19 Allen St Rutland VT

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$139 total

May 31 - Jun 1

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

Align Inn Vermont

5817 Woodstock Rd Quechee VT

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$131 total

May 26 - May 27

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

Woodstock Inn & Resort

Fourteen The Green Woodstock VT

$359 nightly

$395 total

May 25 - May 26

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

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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 $539, 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.