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.
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

3 out of 5
Price was $651, price is now $584 per person
$584
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
This hotel features a seasonal outdoor pool and a hot tub. Enjoy the free ski shuttle and onsite ski storage. Enjoy the sauna and perks like free self parking and free WiFi.
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $700, price is now $604 per person
$604
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Rutland (RUT)
This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $810, price is now $699 per person
$699
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was $1,077, price is now $939 per person
$939
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. A garden is provided and the front desk is staffed around-the-clock.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $776, price is now $677 per person
$677
per person
Nov 22 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Rutland (RUT)
A private beach and a restaurant are featured at this smoke-free lodge. Enjoy the seasonal outdoor pool and perks like free self parking. There's a bar/lounge on site, and a terrace and barbecue grills are also provided.

Top Stockbridge hotels deals

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Free Cancellation
$112 nightly
The price is $123 total per night
$123 total
Oct 25 - Oct 26
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
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Free Cancellation
Reserve now, pay when you stay
$156 nightly
The price is $172 total per night
$172 total
Oct 19 - Oct 20
Total with taxes and fees
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
Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
$206 nightly
The price is $226 total per night
$226 total
Oct 21 - Oct 22
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.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$479 nightly
The price is $527 total per night
$527 total
Nov 2 - Nov 3
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
Mountain Meadows Lodge

Mountain Meadows Lodge

3.5 out of 5
285 Thundering Brook Road Killington VT
$157 nightly
The price is $172 total per night
$172 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features a hot tub and a sauna. Families will appreciate the arcade/game room and picnic area. Relax with a drink at the bar/lounge and enjoy the free buffet breakfast each morning.
Hot Tub
Breakfast included
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$150 nightly
The price is $165 total per night
$165 total
Nov 3 - Nov 4
Total with taxes and fees
A restaurant and a bar/lounge are featured at this bed & breakfast. 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.
Parking included
Free WiFi
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.

Stay near popular Stockbridge attractions

Les Newell Wildlife Management Area

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

Frequently asked questions

How much are vacation packages to Stockbridge?
With vacation packages available for only $584, 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

A snowy ski slope with skiers, a cabin, and a mountain range in the background.
A sign for the Green Mountain National Forest Observation Site in Texas Falls.
A forest with a moss-covered rock and a stream.