Deals on vacations and trips to Stockbridge

Save when you book Stockbridge package deals

Choose two or more items and save on your trip:

Stockbridge flight + hotel vacation packages

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

The Shire Woodstock

3 out of 5
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Hanover Inn Dartmouth

Hanover Inn Dartmouth

4 out of 5
per person
Jul 21 - Jul 25
found 20 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Lebanon (LEB)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A terrace, a lobby fireplace, and a computer station are also on offer.
The Quechee Inn at Marshland Farm

The Quechee Inn at Marshland Farm

3 out of 5
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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.
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) 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 Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
per person
Jul 11 - Jul 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Rutland (RUT)
This motel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A terrace, a garden, and a lobby fireplace are also on offer.

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
$116 nightly
The price is $128 total per night
$128 total
Jun 8 - Jun 9
Total includes 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 hot tub and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
$132 nightly
The price is $145 total per night
$145 total
Jun 17 - Jun 18
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$469 nightly
The price is $516 total per night
$516 total
Jun 8 - Jun 9
Total includes 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

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd, Killington, VT
Free Cancellation
Reserve now, pay when you stay
$129 nightly
The price is $142 total per night
$142 total
Jun 5 - Jun 6
Total includes 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
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
$143 nightly
The price is $157 total per night
$157 total
Jun 17 - Jun 18
Total includes 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
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
$84 nightly
The price is $93 total per night
$93 total
Jun 11 - Jun 12
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. A terrace, a picnic area, and laundry facilities are also on offer.
Breakfast included
Pet friendly
Don't see what you're looking for?
See all available properties in Stockbridge
View all properties
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

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

Belcher Library

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

Belcher Library

Frequently asked questions

How much are vacation packages to Stockbridge?
With vacation packages available for only $882, 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 95 mi from Stockbridge.
Which airport is best for Stockbridge?
Burlington Intl. Airport (BTV) is one of the best airports for Stockbridge. You’ll find it 50 mi northwest of the bustling downtown area. Other options open to you are Lebanon Municipal Airport (LEB) (25 mi away from central Stockbridge) and Rutland Southern Vermont Regional Airport (RUT) (20 mi 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