Alstead Vacations from $635
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Your Alstead Vacation
Excellent adventures await when you reserve a Alstead vacation package. Whether you're a history buff, foodie or just a traveler who loves experiencing new places, there's something for everyone in this interesting city. Any trip to Alstead needs a well-thought-out itinerary. Fill yours with leading attractions like Walpole Mountain View Winery, Walpole Artisans Cooperative and Walpole Artisans Cooperative. Stop daydreaming and start traveling. Explore the broad range of options on Expedia today and put your Alstead vacation plans into motion!
The Latest Alstead vacation packages
Price found within the past 48 hours. Click for updated prices.
1846 Inn and Tavern
$635
per person
Nov 3 - Nov 5
found 18 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
10/10 Exceptional! (1 review)
We went for a girls trip for one night! Everything was amazing from check in to check out! We felt like we were greeting and taking care of our stay. The food is amazing the atmosphere is fantastic and can’t wait till next year!!!!
Reviewed on Sep 21, 2026
The Shire Woodstock
$1,544
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.8/10 Excellent! (994 reviews)
The location of this hotel is perfect. Lovely surroundings too. Plenty of free parking onsite and a coffee station on every floor. Rooms are spotlessly clean and the bed is just so comfortable.
Reviewed on Sep 30, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
$1,267
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (901 reviews)
My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!
Reviewed on Oct 2, 2026
Okemo Mountain Lodging by Vail Resorts
Clock Tower Base Area
$1,761
per person
Dec 17 - Dec 21
found 17 hours ago
Roundtrip non-stop flight included
Miami (MIA) 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
Stay near popular Alstead attractions
Langdon Town Hall
After visiting Langdon Town Hall, make a plan to see the other sights and activities in Langdon.
Alstead Historical Society
You can spend an afternoon exploring the galleries in Alstead Historical Society in Alstead.
Shedd-Porter Memorial Library
Shedd-Porter Memorial Library is just one of the places to see in Alstead, so why not enjoy the other things to explore during your travels?
Mole Hill Theatre
You can get tickets for a performance at Mole Hill Theatre during your trip to Alstead.
Alstead Hotel Deals
Colonial Motel
889 Putney Rd Brattleboro VT
Fully refundableReserve now, pay when you stay
$84 nightly
$93 total
Nov 1 - Nov 2
Total with taxes and fees
6.6/10 (71 reviews)
"I love these kinds of motor lodges and I want them to keep improving and to succeed."
Reviewed on Oct 1, 2026
Pointe at Castle Hill Resort
2940 State Route 103 Cavendish VT
$155 nightly
$168 total
Oct 21 - Oct 22
Total with taxes and fees
8.8/10 Excellent! (1,001 reviews)
"Very nice place, quiet and easily accessible. Room was large with separate large bedroom with door. Large LR with fireplace, sofa & recliner and fully stocked kitchen."
Reviewed on Oct 2, 2026
Latchis Hotel
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$176 nightly
$194 total
Oct 6 - Oct 7
Total with taxes and fees
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 Alstead Vacation Packages
Alstead Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 2,100 |
Top Sights | Walpole Mountain View Winery, Hooper Golf Club and Pitcher Mountain |
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Frequently asked questions
How much does an Alstead vacation package cost?
You can snap up a vacation package to this destination from $635 on Expedia. However, how much your vacation to Alstead costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Alstead?
January, October and December are great times to look for cheap Alstead vacation packages. Opting to travel in less busy months means you can usually find reduced prices on hotels and flights.
How many days is enough for Alstead?
The ideal length of your Alstead vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to hit all the main sights and explore some hidden treasures along the way.
How to find the best Alstead package deals?
Bagging a cheap Alstead package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most economical Alstead package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book an Alstead vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Alstead vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Alstead?
If you're planning a spur-of-the-moment Alstead adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find awesome deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Alstead vacation packages?
Secure your dream trip to Alstead with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for your next payday — we've joined forces with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans let you split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stay on budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
