
Stockbridge Vacations from $706
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Your Stockbridge Vacation
Art, food, entertainment and more … It's all waiting for you with a Stockbridge vacation package. And with the ability to easily customize your city getaway, you know it'll be one that's hard to forget. Any trip to Stockbridge has to include a little sightseeing. White River Golf Club is a popular place to begin exploring. Your perfect Stockbridge vacation is clicks away. Search hotels, flights and more on Expedia for an adventure that's tailored just for you.
The Latest Stockbridge vacation packages
Price found within the past 48 hours. Click for updated prices.

Deerfield Valley Inn
Price was $914, price is now $706 per person
$706
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
9.4/10 Exceptional! (123 reviews)
Very friendly and courteous owner, great location 5 mins away from Mount Snow.
Reviewed on Jul 10, 2026

Vikings Villages Resort
Save 100% on your flight
Price was $1,442, price is now $994 per person
$994
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
10/10 Exceptional! (200 reviews)
We had an amazing stay at Viking Village resort! It is an absolute hidden gem and truly felt like a fairytale escape.
The cozy wooden houses are free-standing, which gives you excellent privacy, making them perfect for either a family trip or a solo getaway. I was so pleasantly surprised to find a fully equipped kitchen inside.
The entire area is incredibly quiet with absolutely no outside noise—just total peace. On the premises, they have a great fireplace setup and the most amazing, cute goats!
My only regret is that we only stayed for one night. We are already hoping to come back for a longer stay next time. It is absolutely worth the drive!
Reviewed on Jul 6, 2026

Latchis Hotel
Save 100% on your flight
Price was $1,172, price is now $842 per person
$842
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Springfield (VSF)
8.6/10 Excellent! (915 reviews)
The air conditioning in the room could not be controlled and required us to sleep with blankets, not pleasant for a warm summer evening.
Reviewed on Jul 15, 2026

Mount Snow Lodging by Vail Resorts
Save 100% on your flight
Price was $1,264, price is now $967 per person
$967
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
7.8/10 Good! (23 reviews)
The bar tender in the lounge on Saturday 10/18 was not friendly. Seemed like he didn’t like his job. He was the only one working and there were not many customers at the bar. Dining room had no one in it. He just was not attentive to me party of 3 who just wanted to order a drink. Fitness center at the Season was very nice but hours were not very accommodating
Reviewed on Oct 20, 2025

Grand Summit Resort, A Vail Resorts Property
Price was $1,059, price is now $822 per person
$822
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
8.6/10 Excellent! (284 reviews)
The room was clean and the facility was fine. Considering it was off season I understand the need to work on the pool and hot tub but it was still disappointing. The deli was outrageously expensive. A coffee was $6 (gas station variety) and a breakfast sandwich $16. Considering the hotel was basically empty I was put in the last room on the second floor, making everything a walk. Staff was fine, a bit indifferent. I was also charged for parking which I understand during peak season but there's literally 10 people staying at this hotel. The additional parking charge just seemed really unnecessary.
Reviewed on Jul 15, 2026
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Stockbridge Hotel Deals

Align Inn Vermont
5817 Woodstock Rd Quechee VT
$135 nightly
The price is $149 total per night from Jul 21 to Jul 22
$149 total
Jul 21 - Jul 22
Total with taxes and fees
9.4/10 Exceptional! (1,250 reviews)
"Cute and quaint but they lied about there being a spa and boutique. They are definitely planning it, but when I stayed 7/6-7/8 they were advertising it as open and it was not. If I wasn’t expecting a spa, this place would have been fine. However, I booked it as a mini wellness retreat, and that was ..."
Reviewed on Jul 15, 2026

Woodstock Inn & Resort
Fourteen The Green Woodstock VT
$504 nightly
The price is $555 total per night from Jul 20 to Jul 21
$555 total
Jul 20 - Jul 21
Total with taxes and fees
9.4/10 Exceptional! (590 reviews)
"As always - best hotel in Vermont."
Reviewed on Jul 12, 2026

Killington Mountain Lodge, Tapestry Collection by Hilton
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $152 total per night from Jul 23 to Jul 24
$152 total
Jul 23 - Jul 24
Total with taxes and fees
7.4/10 Good! (1,001 reviews)
"The property is absolutely gorgeous. Front desk was great. The room I got had a skylite, which is nice but the sun was right in the pillows of the bed, so in the afternoon, if you wanted to take a rest from your days activities, you couldn’t due to the sun being in the pillows, and no way to block ..."
Reviewed on Jul 15, 2026
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.
Find the Best Stockbridge Vacation Packages
Stockbridge Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Lebanon Municipal Airport (LEB) |
Max Temp Winter | 25ºF |
Max Temp Summer | 75ºF |
Top Sights | Lakota Lake, White River Golf Club and Little Pico Mountain |
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