Deals on vacations and trips to Stockbridge

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Stockbridge flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Upper Pass Lodge at Magic Mountain

The Upper Pass Lodge at Magic Mountain

2.5 out of 5
Price was $478, price is now $375 per person
$375
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip 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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $538, price is now $404 per person
$404
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are also on offer.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Save 100% on your flight
Price was $772, price is now $582 per person
$582
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Lebanon (LEB)
This resort features a restaurant, an indoor pool, and a bar/lounge. There's an outdoor tennis court on site, and a fireplace in the lobby and a picnic area are also provided.
Chalet 239

Chalet 239

2 out of 5
Save 100% on your flight
Price was $625, price is now $475 per person
$475
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
Price was $2,420, price is now $1,858 per person
$1,858
per person
Oct 2 - Oct 6
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.

Top Stockbridge hotels deals

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
$107 nightly
The price is $118 total per night
$118 total
Aug 24 - Aug 25
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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night
$494 total
Sep 1 - Sep 2
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
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
$198 nightly
The price is $218 total per night
$218 total
Aug 27 - Aug 28
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
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd, Quechee, VT
Free Cancellation
Reserve now, pay when you stay
$132 nightly
The price is $145 total per night
$145 total
Aug 24 - Aug 25
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
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Free Cancellation
Reserve now, pay when you stay
$101 nightly
The price is $111 total per night
$111 total
Aug 31 - Sep 1
Total with taxes and fees
A restaurant and an indoor pool are featured at this hotel. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the sauna and free perks like on-the-go breakfast and free self parking.
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
$84 nightly
The price is $93 total per night
$93 total
Aug 31 - Sep 1
Total with 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
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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

Frequently asked questions

How much are vacation packages to Stockbridge?
With vacation packages available for only $375, 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