Deals on vacations and trips to Stockbridge

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Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $748, price is now $662 per person
$662
per person
Feb 3 - Feb 6
found 8 hours ago
Roundtrip flight included
Fort Walton Beach (VPS) 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.
Mountain Green Resort

Mountain Green Resort

4 out of 5
Price was $1,570, price is now $1,243 per person
$1,243
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to Rutland (RUT)
An outdoor pool is featured at this apartment, along with a virtual front desk. Take advantage of the free self parking.
The Suites at Killington Center

The Suites at Killington Center

3.5 out of 5
Price was $1,145, price is now $963 per person
$963
per person
Feb 3 - Feb 6
found 8 hours ago
Roundtrip flight included
Fort Walton Beach (VPS) to Rutland (RUT)
An outdoor pool, free self parking, and laundry facilities are featured at this condo. WiFi in public areas is free. Concierge services and a virtual front desk are also provided.
Hanover Inn Dartmouth

Hanover Inn Dartmouth

4 out of 5
Price was $946, price is now $810 per person
$810
per person
Feb 3 - Feb 6
found 8 hours ago
Roundtrip flight included
Fort Walton Beach (VPS) 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 Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
Price was $1,130, price is now $1,005 per person
$1,005
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
Fort Myers (RSW) to Rutland (RUT)
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.

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
$109 nightly
The price is $120 total per night
$120 total
Jan 4 - Jan 5, 2026
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
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
$144 nightly
The price is $158 total per night
$158 total
Jan 4 - Jan 5, 2026
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
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
$188 nightly
The price is $207 total per night
$207 total
Jan 21 - Jan 22, 2026
Total with 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 Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Get rates
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

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night
$395 total
Jan 19 - Jan 20, 2026
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
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
Free Cancellation
Reserve now, pay when you stay
$120 nightly
The price is $132 total per night
$132 total
Jan 4 - Jan 5, 2026
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
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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 Gaysville.

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 $662, 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