Book Exclusive Stockbridge Vacation Packages

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Stockbridge flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Killington Resort and Fire Tower are located nearby.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
per person
Sep 5 - Sep 7
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this 4-star B&B in Jericho. Enjoy free breakfast, free WiFi, and in-room massages. Our guests praise the breakfast in our reviews. Popular attractions Veterans' Park and Mills Riverside Park are located nearby.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.

Top Stockbridge hotels deals

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $170 per night
CA $170
CA $187 total
Aug 18 - Aug 19
includes taxes & fees
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.
Pool
Hot tub
White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $154 per night
CA $154
CA $169 total
Aug 10 - Aug 11
includes taxes & fees
Book a stay at this business-friendly hotel in White River Junction. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Upper Valley Aquatic Center and Briggs Opera House are located nearby.
Pool
Breakfast included
Super 8 by Wyndham White River Junction

Super 8 by Wyndham White River Junction

2 out of 5
442 North Hartland Rd, I-91 Exit 11 Rt 5 S 1/4 Mile, White River Junction, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $114 per night
CA $114
CA $126 total
Jul 27 - Jul 28
includes taxes & fees
Book a stay at this business-friendly motel in White River Junction. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Upper Valley Aquatic Center and Briggs Opera House are located nearby.
Breakfast included
Pet-friendly
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $611 per night
CA $611
CA $732 total
Aug 17 - Aug 18
includes taxes & fees
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
The price is CA $243 per night
CA $243
CA $267 total
Jul 24 - Jul 25
includes taxes & fees
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Black Dog Sports are located nearby.
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
The price is CA $162 per night
CA $162
CA $178 total
Jul 28 - Jul 29
includes taxes & fees
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Quechee Gorge Village are located nearby.
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.

Popular places to visit

Belcher Library

After visiting Belcher Library, make a plan to see the other sights and activities in Stockbridge.

Belcher Library

Les Newell Wildlife Management Area

You can take time to visit Les Newell Wildlife Management Area during your travels to Stockbridge.

Les Newell Wildlife Management Area

Stockbridge Vacations

Collect new memories, have epic adventures and follow the path less traveled — it's all possible in Stockbridge. But first, let us fill you in on a few basics about your next vacation destination!

If you journey 17 miles (27 kilometers) northeast of Rutland, or 25 miles (40 kilometers) west of Lebanon, you'll find yourself in Stockbridge.

Places to visit in Stockbridge

Getting out on the green is a great way to enjoy the fresh air and have a blast. Challenge yourself with a round at White River Golf Club. Need some more ideas? Whether you decide to speed across it, horse around in it or explore beneath it, few things are as joyful as a day spent around water. Add some wonderful aquatic excitement to your vacation at Vermont River Tubing.

Where do you fly into for Stockbridge?

Put on your headphones and watch a couple of in-flight movies. Before you know it, you'll touch down at Rutland Southern Vermont Regional Airport (RUT). It's about 20 miles (32 kilometers) from downtown Stockbridge.

Frequently asked questions

How much are vacation packages to Stockbridge?
With vacation packages available for only CA $940, you won't need to drain your bank balance to visit Stockbridge. Travelocity is here to help. Bundle your hotels, flights and experiences into a package and receive some excellent discounts. The more you book, the greater the savings.
Where can I get the best vacation package deals for Stockbridge?
For an amazing Stockbridge package deal, you can't go past Travelocity. Select from 400 partner airlines and 1,000,000 properties worldwide to create the ideal escape — it's really that easy.
Why should I book my Stockbridge vacation bundle with Travelocity?
Because you'll never wander alone if you book through us, and we offer round-the-clock support and superb service to boot. Add to that our Price Match Guarantee and tons of experiences and destinations to choose from. We're here to make your vacation as unforgettable as possible.
Will I save money on my Stockbridge car rental if I combine it with my hotel or flight?
Sure can — combine your car, flight and hotel into a Stockbridge vacation package and you can save tons. With so much to see and do in the Stockbridge area, having your own set of wheels will come in handy. Once you've settled into the driver's seat, turn up the tunes and make your way to The Egg, a top sight approximately 153 kilometers from Stockbridge.
Which airport is best for Stockbridge?
Burlington Intl. Airport (BTV) is one of the best airports for Stockbridge. You'll find it 80 kilometers northwest of the bustling downtown area. Other options open to you are Lebanon Municipal Airport (LEB) (40 kilometers away from central Stockbridge) and Rutland Southern Vermont Regional Airport (RUT) (32 kilometers away from central Stockbridge).
Where should I stay when visiting Stockbridge?
The Ski, snow mobile, hiking, fun on slopes & trails! is popular with many travelers. Book now before it's too late.

Photos of local treasures

Browse Stockbridge vacation photos for more inspiration