Walpole Vacations from $915

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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.
Deerfield Valley Inn

Deerfield Valley Inn

$915
per person
Dec 30 - Jan 6
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to Springfield (VSF)
9.4/10 Exceptional! (133 reviews)
Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Base Area
Save 100% on your flight
$1,864
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8.6/10 Excellent! (908 reviews)
This is our second time staying at Jackson gore. The room was perfect. We were looking forward to spending some time in the outdoor hot tubs and was told they were under maintenance which was unfortunate. Also we were booked the weekend after the ending of summer activities (mini golf and mountain coaster) but they had posters hung all over advertising the Halloween glow mini golf and scary mountain coaster event the weekend after we left. We really loved the mini golf last year so that was unfortunate that they didn't choose to continue this on the off week in between. Overall, we will be back again next year! Maybe the week before so we can catch more amenities. We love Ludlow VT and the easy access to everything near by while staying at Jackson Gore.

Reviewed on Oct 19, 2026

Okemo Mountain Lodging  by Vail Resorts

Okemo Mountain Lodging by Vail Resorts

Clock Tower Base Area
Save 100% on your flight
$4,982
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
7.8/10 Good! (28 reviews)
Don’t ever rent at this place for the condo rentals they sent us to the wrong address, I could not get in contact with the so-called property manager for over an hour or more. We had no toilet paper, we had no hairdryer, no paper towels, we didn’t even know where the keys were or shampoo or soap. Basically this was an utter disaster. I tried to work it out with resort management and they offered certain things and I countered and I got at that point what I wanted, but it just continued to spiral downhill and then when I communicate further issues, I had to be on the phone with them, trying to explain to them what the problem was up until 11 PM at night, that night was in the 30s and they left the air conditioner on in the house didn’t warm up until after 1 AM. This was by far the worst experience I’ve ever had with a supposedly high-end resort. I’m telling you do not rent from their condo selection. It’s terrible. It’s expensive and it is just a waste of time.

Reviewed on Oct 15, 2026

Mountain Lodge at Okemo, A Vail Resorts Property

Mountain Lodge at Okemo, A Vail Resorts Property

Clock Tower Base Area
$1,688
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8/10 Very Good! (225 reviews)
Great location! But…. Two recommendations. Property should have been maintained better (we found cockroaches inside coffee machines). There was no instruction to collect the keys from a different location. Kinda embarrassing.

Reviewed on Oct 17, 2026

The Shire Woodstock

The Shire Woodstock

$1,150
per person
Jan 4 - Jan 9
found 15 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.8/10 Excellent! (997 reviews)
Perfect location walk into town

Reviewed on Oct 18, 2026

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Stay near popular Walpole attractions

North Walpole Village Park

This peaceful community park offers green spaces and Connecticut River views for picnics and casual strolls. Enjoy the tranquil setting during spring through fall when foliage creates a picturesque backdrop.
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Drewsville Village Green

This historic village green showcases 19th-century New England architecture, including the 1836 stone church. Stroll through this tranquil setting to appreciate the preserved buildings.
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Hooper Golf Club

This classic 9-hole Stiles and Van Kleek course ranks among the world's finest, challenging players with undulating fairways. Experience strategic golf amid serene New England landscapes.
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Walpole Farmers Market

This vibrant growers' market showcases Walpole's agricultural bounty on the historic Town Common. Browse fresh produce, artisanal foods, and local crafts while connecting directly with the farmers who grew your dinner.
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Hooper Golf Course

Ranked #13 worldwide by GOLF Magazine, this classic 9-hole course features rolling hills and strategic play by Stiles and Van Kleek. Enjoy a round followed by local craft beers at the historic Watkins Tavern clubhouse.
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Bridge Memorial Library

This historic library, established in 1891 by the Bridge Family, has served Walpole's community for over a century. Browse its diverse collection in a building that honors both heritage and modern needs.
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Walpole Artisans Cooperative

This cooperative gallery showcases handcrafted treasures from over 20 local artisans. Meet the makers as you browse unique woodwork, glass art, jewelry, and fiber arts in this welcoming creative space.
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Walpole Hotel Deals

Colonial Motel

Colonial Motel

889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$99 nightly
$109 total
Nov 1 - Nov 2
Total with taxes and fees
6.2/10 (101 reviews)
"Unknown to us, the property is under new management and is currently under construction and still organizing. Although the property itself was nice, rooms had a lot of room, but smelly. Hallways smelled like Skunk, because entry doors do not shut tight, for the animal to enter with no problem. Used ..."

Reviewed on Oct 19, 2026

Colonial Motel
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

2940 State Route 103 Cavendish VT
$147 nightly
$160 total
Nov 19 - Nov 20
Total with taxes and fees
Pointe at Castle Hill Resort
Latchis Hotel

Latchis Hotel

50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$136 nightly
$150 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (1,011 reviews)
"Had a wonderful stay. Great room with a beautiful view of the mountains. And we absolutely loved that every room had a record player with historic records to play and enjoy - what a cool feature!"

Reviewed on Oct 18, 2026

Latchis Hotel
See all 655 properties in Walpole
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 Walpole Vacation Packages

Walpole Essential Information

Language
English
Currency
U.S dollars
Population
610
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Walpole Mountain View Winery, Hooper Golf Club and Walpole Artisans Cooperative

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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 $915 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.