Deals on vacations and trips to Stockbridge

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Price found within the past 48 hours. Click for updated prices.
Follansbee Inn

Follansbee Inn

3 out of 5
North Sutton
Price was $646, price is now $570 per person
$570
per person
Nov 14 - Nov 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Lebanon (LEB)
A bar/lounge and a garden are featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like full breakfast and WiFi in public areas. A lobby fireplace, a library, and a picnic area are also on offer.
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $707, price is now $601 per person
$601
per person
Oct 21 - Oct 26
found 13 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
This hotel features an indoor pool and a sauna. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Castle Hill Resort And Spa

Castle Hill Resort And Spa

3.5 out of 5
Price was $848, price is now $733 per person
$733
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury hotel. Enjoy the indoor pool and perks like free self parking and free WiFi. You'll appreciate the gym, bar/lounge, and concierge services.
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
Price was $783, price is now $683 per person
$683
per person
Oct 23 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Greenbrier Inn

Greenbrier Inn

2 out of 5
Price was $883, price is now $780 per person
$780
per person
Oct 21 - Oct 26
found 13 hours ago
Roundtrip flight included
Nashville (BNA) to Rutland (RUT)
This hotel features free WiFi in public areas, concierge services, and free self parking. Free continental breakfast is served. A garden, a lobby fireplace, and a library are also on offer.

Top Stockbridge hotels deals

Align Inn Vermont

Align Inn Vermont

2.5 out of 5
5817 Woodstock Rd Quechee VT
$221 nightly
The price is $243 total per night
$243 total
Oct 18 - Oct 19
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
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 18 - Oct 19
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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$859 nightly
The price is $945 total per night
$945 total
Sep 22 - Sep 23
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
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
$204 nightly
The price is $225 total per night
$225 total
Sep 27 - Sep 28
Total with taxes and fees
This hotel features a 24-hour gym and a hot tub. Traveling on business? Take advantage of the 2 conference rooms, along with free WiFi in public areas. Self parking, a terrace, and a lobby fireplace are also offered.
Hot Tub
Pet friendly
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
$325 nightly
The price is $358 total per night
$358 total
Sep 22 - Sep 23
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
Emrose Luxury Cabins

Emrose Luxury Cabins

2 out of 5
1246 Franklin Street Brandon VT
$185 nightly
The price is $203 total per night
$203 total
Sep 22 - Sep 23
Total with taxes and fees
This hotel's 8 hot tubs and 24-hour gym are among the featured amenities. Families will appreciate the arcade/game room and picnic area. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi.
Pool
Hot Tub
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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.

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.
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Frequently asked questions

How much are vacation packages to Stockbridge?
With vacation packages available for only $570, 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.