Stockbridge Holidays from £3,214

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Your Stockbridge Holiday

Art, food, entertainment and more … It's all waiting for you with a Stockbridge holiday package. And with the ability to easily customise 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 holiday is clicks away. Search hotels, flights and more on Expedia for an adventure that's tailored just for you.

The Latest Stockbridge Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock

The Shire Woodstock

3 out of 5
per person
15 Sept - 20 Sept
found 1 day ago
Return flight included
London (LON) to Springfield (VSF)
8.8/10 Excellent! (762 reviews)
Great location!! Very accommodating and clean.

Reviewed on 28 Jun 2025

Spacious Dartmouth College Home on Occum Pond

Spacious Dartmouth College Home on Occum Pond

2 out of 5
per person
15 Sept - 20 Sept
found 1 day ago
Return flight included
London (LON) to Lebanon (LEB)
No reviews
Brookside Hideaway, Brook Road Inn

Brookside Hideaway, Brook Road Inn

3.5 out of 5
per person
15 Sept - 20 Sept
found 1 day ago
Return flight included
London (LON) to Lebanon (LEB)
10/10 Exceptional! (1 review)
Stay At Jimmy's

Stay At Jimmy's

3 out of 5
per person
15 Sept - 20 Sept
found 1 day ago
Return flight included
London (LON) to Springfield (VSF)
10/10 Exceptional! (31 reviews)
Every little detail is taken care of... Every thought for the customers convenience. Q-tips! What hotel supplies Q-tips? We were lucky enough to meet Jimmy... Nice guy, very welcoming. Snacks, beverages... Fresh muffins and coffee. I can't say enough about how wonderful our stay was... Price was very low for what you get. Highly recommend

Reviewed on 27 Jun 2025

Golden Stage Inn B&B

Golden Stage Inn B&B

3.5 out of 5
per person
15 Sept - 20 Sept
found 1 day ago
Return flight included
London (LON) to Rutland (RUT)
10/10 Exceptional! (26 reviews)
Family run B&B close to Okemo. Wonderful hosts.

Reviewed on 22 Jan 2025

Lincoln Inn & Gallery

Lincoln Inn & Gallery

3 out of 5
West Woodstock
per person
15 Sept - 20 Sept
found 1 day ago
Return flight included
London (LON) to Springfield (VSF)
9.6/10 Exceptional! (10 reviews)
Nice view with spacious grounds. I see potential for lovely garden with a little help

Reviewed on 25 Jun 2025

Stockbridge Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Max Temp Winter
-3.89ºC
Max Temp Summer
24ºC
Top Sights
Lakota Lake, Little Pico Mountain and White River Golf Club

Our pick of the best Stockbridge Hotel Deals

Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
2.5 out of 5
19 Allen St, Rutland, VT
Stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in ...
8/10 Very Good! (1,001 reviews)
"I believe I already submitted a review, but this was a great place to stay, convenient, clean, and friendly."

Reviewed on 26 Jun 2025

Comfort Inn Rutland - Killington
White River Inn and Suites
White River Inn and Suites
2.5 out of 5
91 Ballardvale Drive, White River Junction, VT
Stay at this business-friendly hotel in White River Junction. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and ...
7/10 Good! (1,002 reviews)
"It’s obvious they’re in the middle of renovating their building. It was clean. It was quiet and convenient."

Reviewed on 22 Jun 2025

White River Inn and Suites
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free Wi-Fi, free valet parking and an outdoor pool. Our guests praise the helpful staff in their reviews. ...
9.2/10 Wonderful! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."

Reviewed on 20 Jun 2025

Woodstock Inn & Resort
See all 2,085 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Stockbridge travel package cost?
Live it up in Stockbridge from just £3,214. Choose from a great selection of hotels, flights and rental cars to suit your budget. Pick up even more discounts when you add a couple of sightseeing tours to your travel package.
If I'm not able to travel, can I cancel my Stockbridge travel package?
Don't stress if you're rethinking your Stockbridge travel package --- you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We understand life can sometimes throw you a curveball, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.
How do I get a cheap travel package to Stockbridge?
Crafting your own Stockbridge travel package with Expedia is a smart way to save. We offer more than 550 partner airlines and 1,000,000 hotels around the world. With such a wonderful range to select from, you'll have no difficulty putting together your perfect adventure.
Does Expedia offer Book Now, Pay Later Stockbridge holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has devised a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a dream getaway without making a dent in your savings. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's monthly instalment plans. If making small repayments each month works for you, pick this option at checkout.
  • Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan from Klarna.

What are the top hotels in Stockbridge?
Lock in a room at White River Inn and Suites. It's one of the area's most popular properties. Another well-known option in Stockbridge is Hotel Coolidge.
How far in advance should I book my Stockbridge holiday?
Travellers are usually able to browse international fares on Expedia up to a year in advance of departure. Booking at the last minute? With a stroke of luck, it's still possible to purchase an affordable ticket only weeks before your flight.
What does an Expedia Stockbridge travel package include?
Expedia has all you need to lock in Stockbridge escape, but how your package is structured is totally up to you. Select from a combination of rental cars, flights and hotels. Looking for a few activities to keep you on the go? Once you've made your booking, you can add them too. No matter your budget or style, there's a package to match your needs.
What should I know before booking a Stockbridge travel package?
When you book your flights, hotels and car rentals together, you'll be rewarded with amazing discounts. Whether you're organising a beach escape in a villa or would rather stay in a ritzy city hotel, Expedia can make it happen for less.
Can I choose my airline with a Stockbridge Expedia travel package?
Yes --- that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 partner airlines throughout the world, so you have loads of choice when organising your Stockbridge escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.