Walpole Vacations from $983
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Walpole Vacation Packages
- Jackson Gore Village, A Vail Resorts Property
Sep 8 - Sep 14Jackson Gore Village, A Vail Resorts Property + Flight
Jackson Gore Base Area6 nights3.0 star property8.6/10 - Excellent (876 reviews)"Staff, room, and amenities were awesome. Would stay here again in a heartbeat. A few hot tubs to chose from for adults and pool for kids."Reviewed July 26, 2026Roundtrip • Chicago (CHI) - Springfield (VSF)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,171$983found 1 day agoper traveler - The Shire Woodstock
Oct 19 - Oct 25The Shire Woodstock + Flight
Woodstock5 nights3.0 star property8.8/10 - Excellent (969 reviews)"It would be great to have a coffee maker in the room"Reviewed July 31, 2026Roundtrip • Denver (DEN) - Springfield (VSF)DEN - LEB • 1 stop LEB - DEN • 1 stop$2,515$1,918found 1 day agoper traveler - Winterplace at Okemo, A Vail Resorts Property
Sep 8 - Sep 14Winterplace at Okemo, A Vail Resorts Property + Flight
Clock Tower Base Area6 nights4.0 star property8.8/10 - Excellent (27 reviews)"Enjoyable and beautiful place. Ann"Reviewed July 20, 2026Roundtrip • Chicago (CHI) - Springfield (VSF)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,508$1,265found 1 day agoper traveler - Solitude Village at Okemo by Vail Resorts
Sep 8 - Sep 14Solitude Village at Okemo by Vail Resorts + Flight
Clock Tower Base Area6 nights4.0 star property7.8/10 - Good (35 reviews)Roundtrip • Chicago (CHI) - Springfield (VSF)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,278$1,091found 1 day agoper traveler - Okemo Mountain Lodging by Vail Resorts
Sep 8 - Sep 14Okemo Mountain Lodging by Vail Resorts + Flight
Clock Tower Base Area6 nights3.5 star property7.8/10 - 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 June 26, 2025Roundtrip • Chicago (CHI) - Springfield (VSF)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,180$1,016found 1 day agoper traveler
Discover the most popular places to visit in Walpole
Walpole Hotel Deals
Keene Elm City Hotel, an Ascend Collection Hotel
Keene Elm City Hotel, an Ascend Collection Hotel
Frequently Asked Questions
How much does a Walpole vacation package cost?
You can grab a vacation package to this destination from $983 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.