Book Exclusive Stockbridge Vacation Packages
Stockbridge flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Mountaineer Inn
per person
Jun. 16 - Jun. 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.
Lake Bomoseen Lodge
per person
Jun. 16 - Jun. 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this 3.5-star beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Prospect Bay Country Club and Lake Bomoseen are located nearby.
Farm Road Estate
per person
Jun. 16 - Jun. 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
Stay at this 3-star golf hotel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
The Upper Pass Lodge at Magic Mountain
per person
Jun. 16 - Jun. 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
Stay at this motel in Londonderry. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Magic Mountain Ski Resort and Lowell Lake State Park are located nearby.
Top Stockbridge hotels deals
Comfort Inn Rutland - Killington
19 Allen St, Rutland, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $161 per night
CA $161
CA $177 total
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Vermont State Fairgrounds and Green Mountain Shopping Plaza are located nearby.
Pool
Hot tub
Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd, Killington, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $170 per night
CA $170
CA $186 total
includes taxes & fees
Apr 28 - Apr 29
Stay at this 3.5-star ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
Hot tub
Pet-friendly
Align Inn Vermont
5817 Woodstock Rd, Quechee, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $157 per night
CA $157
CA $173 total
includes taxes & fees
May 12 - May 13
Book a stay at this business-friendly hotel in Quechee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Quechee Gorge Bridge and Quechee Gorge Village are located nearby.
Pool
Breakfast included
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is CA $429 per night
CA $429
CA $533 total
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Woodstock Town Hall Theatre and Red Wagon Toy Company are located nearby.
Pool
Hot tub
The Mountain Inn at Killington
47 Old Mill Rd, Killington, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $189 per night
CA $189
CA $219 total
includes taxes & fees
Apr 25 - Apr 26
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort are located nearby.
Pool
Breakfast included
My Place Hotel-Randolph VT
2440 Vermont 66, Randolph Center, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $168 per night
CA $168
CA $183 total
includes taxes & fees
May 1 - May 2
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.
Pet-friendly
Parking included
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.
Les Newell Wildlife Management Area
You can take time to visit Les Newell Wildlife Management Area during your travels to Stockbridge.
Stockbridge Vacations
Collect new memories, have epic adventures and follow the path less traveled — it's all possible in Stockbridge. But first, let us fill you in on a few basics about your next vacation destination!
If you journey 17 miles (27 kilometers) northeast of Rutland, or 25 miles (40 kilometers) west of Lebanon, you'll find yourself in Stockbridge.
Places to visit in Stockbridge
Getting out on the green is a great way to enjoy the fresh air and have a blast. Challenge yourself with a round at White River Golf Club. Need some more ideas? Whether you decide to speed across it, horse around in it or explore beneath it, few things are as joyful as a day spent around water. Add some wonderful aquatic excitement to your vacation at Vermont River Tubing.Where do you fly into for Stockbridge?
Put on your headphones and watch a couple of in-flight movies. Before you know it, you'll touch down at Rutland Southern Vermont Regional Airport (RUT). It's about 20 miles (32 kilometers) from downtown Stockbridge.Frequently asked questions
Photos of local treasures
Browse Stockbridge vacation photos for more inspiration