Walpole Vacations from $537

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Your Walpole Vacation

Excellent adventures await when you book a Walpole vacation package. Whether you're a history buff, art enthusiast or just a traveler who loves to experience new places, there's something for everyone in this lively city. A trip to Walpole is an ideal opportunity to see the sights. Check out big-name attractions such as Hooper Golf Club, Walpole Mountain View Winery and Walpole Artisans Cooperative. Expedia will help you escape the everyday. Tailor your vacation to Walpole to suit your style of travel, whatever that may look like.

The Latest Walpole vacation packages

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

The Shire Woodstock

3 out of 5
Price was $656, price is now $537 per person
$537
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
Another perfect stay at the Shire! Staff wonderful and the room and view perfect!

Reviewed on Dec 11, 2025

Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $1,963, price is now $1,577 per person
$1,577
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.

Reviewed on Jun 26, 2025

Windham Hill Inn

Windham Hill Inn

4 out of 5
Price was $926, price is now $764 per person
$764
per person
Feb 19 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (37 reviews)
The Inn is situated near the top of a mountain and surrounded by other hilltops. There are trails that help you to reconnect with nature. Our room was lovely and comfortable. There is a attention to detail in the decor of this establishment which is both delightful and humorous.

Reviewed on Jul 11, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,120, price is now $931 per person
$931
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town

Reviewed on Nov 26, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,148, price is now $955 per person
$955
per person
Jan 24 - Jan 27
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good.

Reviewed on Nov 30, 2025

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Discover the most popular places to visit in Walpole

Walpole Farmers Market

You can find the perfect gifts to bring home at Walpole Farmers Market during your visit to Walpole. You can seek out the ski slopes while in the area.

Walpole Farmers Market

Pete's Stand Vegetables

Enjoy an outing to Pete's Stand Vegetables during your stay in Walpole. You can enjoy the coffeehouses while in the area.

Pete's Stand Vegetables

Find the Best Walpole Vacation Packages

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Frequently asked questions

How much does a Walpole vacation package cost?
You can grab a vacation package to this destination from $537 on Expedia. However, how much your vacation to Walpole costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Walpole?
January, October and December are great times to look for cheap Walpole vacation packages. Traveling in less busy months means you can usually find better prices on flights and hotels.
How many days is enough for Walpole?
With a well-organized travel plan, you can easily tick off the top Walpole attractions in a few days. But if you want to discover hidden gems or take day trips, consider booking your Walpole vacation for longer.
Is it worth booking a vacation package to Walpole?
Walpole has everything you need for an unforgettable getaway. Begin your Walpole vacation on a high note by checking out popular attractions like Hooper Golf Club.
How to find the best Walpole package deals?
Start your search for a Walpole package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the perfect Walpole package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Walpole adventure off to a flying start.
Is it cheaper to book a Walpole vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still have the freedom to create a personalized Walpole vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Walpole?
If you're planning an impromptu Walpole trip, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Walpole vacation packages?
Your Walpole getaway is meant to be a relaxing escape from your busy life, not a reason for money-related stress. So to give you a bit more flexibility, we've joined up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.