Stockbridge Vacations from $404

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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.
The Putney Inn

The Putney Inn

2.5 out of 5
Price was $508, price is now $404 per person
$404
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
8.4/10 Very Good! (1,005 reviews)
My stay here was perfect for what I was looking for, just a one night stay in the area. The property is dated but the accommodations are clean and the surrounding area is extremely quiet and secluded, but the parking lot is well lit and safe. I would stay here again if I needed a short term accommodation.

Reviewed on Aug 22, 2025

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
Price was $1,358, price is now $1,005 per person
$1,005
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Lebanon (LEB)
9/10 Wonderful! (732 reviews)
Great place to stay and see the beautiful mt ascutney

Reviewed on Aug 24, 2025

North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
Price was $1,622, price is now $1,274 per person
$1,274
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
8.6/10 Excellent! (1,006 reviews)
We stayed at the resort for a week. It was very nice. Pool was very clean, as well as the property. Staff were just fabulous, always willing to help. I look forward to staying there again

Reviewed on Aug 25, 2025

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
Price was $555, price is now $444 per person
$444
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Rutland (RUT)
6.4/10 (1,005 reviews)
Clean and comfortable. Good value for what you get. Would stay again.

Reviewed on Aug 18, 2025

The Vermont Inn

The Vermont Inn

3 out of 5
Price was $1,124, price is now $939 per person
$939
per person
Sep 30 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Rutland (RUT)
9.2/10 Wonderful! (407 reviews)
Was a wonderful little bed and breakfast. Will stay here again.

Reviewed on Jul 23, 2025

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Stockbridge Hotel Deals

White River Inn and Suites

White River Inn and Suites

2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $117 total per night from Sep 14 to Sep 15
$117 total
Sep 14 - Sep 15
Total with taxes and fees
7/10 Good! (1,000 reviews)
"The staff was the best part of this stay. They were friendly and welcoming. The room was very spacious and comfortable for the price."

Reviewed on Aug 13, 2025

White River Inn and Suites
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$439 nightly
The price is $483 total per night from Sep 1 to Sep 2
$483 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (532 reviews)
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."

Reviewed on Jul 30, 2025

Woodstock Inn & Resort
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd, Killington, VT
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $144 total per night from Aug 27 to Aug 28
$144 total
Aug 27 - Aug 28
Total with taxes and fees
9/10 Wonderful! (874 reviews)
We’ll be back.
"Beautiful area, outside of facility looks dated, but that’s not realistic to change. Inside has had a nice update. The staff is very friendly and helpful. We had an inconsiderate and noisy person upstairs over us, just a matter of who is there. We would surely stay here again."

Reviewed on Aug 23, 2025

The Mountain Inn at Killington
See all 2,073 properties in Stockbridge
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.

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Frequently asked questions

How much does a Stockbridge vacation package cost?
Offering great value package deals from $404 on Expedia, you'll be thrilled with how little a vacation to Stockbridge costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Stockbridge?
You can typically find reduced prices and greater availability in March, May and October. Explore our cheap Stockbridge vacation packages and you could get some great off-season deals.
How many days is enough for Stockbridge?
Generally, a handful of days is enough to visit the top attractions during your Stockbridge vacation. However, if you want to have some time to rest or go on day trips, consider extending your trip.
How to find the best Stockbridge package deals?
Landing a cheap Stockbridge package deal is easy with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, apply some filters and see what's available. You can personalize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most economical Stockbridge package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Stockbridge vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Stockbridge vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Stockbridge?
Secure incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Stockbridge escape.
Does Expedia offer Book Now, Pay Later Stockbridge vacation packages?
Your Stockbridge trip should be a relaxing escape from your busy life, not a source of money-related stress. So to allow you extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.