Search Deals onStockbridge Vacation Packages
Stockbridge Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Green Trails Inn
Price was $417, price is now $360 per person
$360
per person
Nov 20 - Nov 22
found 7 hours ago
Roundtrip flight included
New York (NYC) to Lebanon (LEB)
Stay at this inn in Brookfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Brookfield Free Public Library and Allis State Park are located nearby.
One of the nicest BNB’s we’ve stayed at. Josh and staff were so accommodating and nice. Breakfast was great. We will totally be back at some point. Thanks again Josh!
Reviewed on Aug 19, 2026
My Place Hotel-Randolph VT
Price was $1,418, price is now $1,122 per person
$1,122
per person
Oct 3 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture and Montague Golf Club are located nearby.
Very pleasant experience from checking in to when we left. Very helpful front desk staff and hotel was very clean.
Reviewed on Aug 30, 2026
The Shire Woodstock
Price was $1,322, price is now $1,048 per person
$1,048
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Lake Bomoseen Lodge
Price was $717, price is now $570 per person
$570
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this 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.
Stone Hearth Inn and Eatery
Price was $1,268, price is now $1,058 per person
$1,058
per person
Sep 30 - Oct 4
found 4 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located nearby.
We had a lovely stay at Stone Hearth Inn! Very quaint place and comfortable, clean accommodations. Beautiful grounds around the property with outside seating to enjoy the fresh air. The dinner we had at the attached “Eatery” was awesome!!! So was the amazingly delicious included breakfast. Vickie was so welcoming and kind.
We can’t say enough good things! Highly recommend
Reviewed on Aug 30, 2026
Latchis Hotel
Price was $1,096, price is now $923 per person
$923
per person
Oct 9 - Oct 12
found 4 hours ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
Mountain Green Resort
Price was $1,154, price is now $983 per person
$983
per person
Nov 5 - Nov 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Rutland (RUT)
Book a stay at this business-friendly apartment in Killington. Enjoy free WiFi, free parking, and in-room washers/dryers. Popular attractions Killington Resort and Black Dog Sports are located nearby.
I can show pictures of the unit that was very different than described. I paid extra for a Mountain View for 3 nights - and it was not Mountain View. We were in a different building at the bottom of the hill a 8 min freeezing cold and icy walk to the pool area.
Reviewed on Jan 28, 2026
Bentley House Bed and Breakfast
Price was $651, price is now $556 per person
$556
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip flight included
New York (NYC) to Rutland (RUT)
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park are located nearby.
very clean, very friendly, good breakfast, very nice Victorian style house
Reviewed on Aug 25, 2026
Stockbridge Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Stockbridge Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
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