Hinsdale Vacations from $780

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The Latest Hinsdale vacation packages

Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $891, price is now $780 per person
$780
per person
Oct 2 - Oct 5
found 11 hours ago
Roundtrip flight included
Chicago (ORD) to Springfield (VSF)
10/10 Exceptional! (114 reviews)
Holy and Kyle were awesome! Such wonderful breakfasts each day we were there, delicious! So close to everything we wanted to see. We look forward to coming back for our next Vermont getaway!

Reviewed on Jun 19, 2026

Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was $1,457, price is now $1,238 per person
$1,238
per person
Oct 1 - Oct 6
found 8 hours ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
9.2/10 Wonderful! (120 reviews)
We truly enjoyed the Stone Hearth Inn. We stayed after an event about a half hour away. The Inn was cozy, decorated tastefully with cozy white coaches and antiques and wide plank flooring. The room was air conditioned , the bed was comfy and had everything we needed in the bathroom. We enjoyed speaking with the owner at breakfast and hearing her story. Just a few minutes from town and a great place. We enjoyed the breakfast but, unfortunately , weren’t staying long enough to try lunch or dinner at the eatery (run by CIA graduate). Next time! Thank you!

Reviewed on Jun 22, 2026

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $1,163, price is now $1,015 per person
$1,015
per person
Oct 1 - Oct 6
found 8 hours ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
8.6/10 Excellent! (862 reviews)
Great family friendly location!

Reviewed on Jul 11, 2026

Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was $1,257, price is now $1,097 per person
$1,097
per person
Oct 1 - Oct 6
found 8 hours ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
7.8/10 Good! (23 reviews)
The bar tender in the lounge on Saturday 10/18 was not friendly. Seemed like he didn’t like his job. He was the only one working and there were not many customers at the bar. Dining room had no one in it. He just was not attentive to me party of 3 who just wanted to order a drink. Fitness center at the Season was very nice but hours were not very accommodating

Reviewed on Oct 20, 2025

Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $1,363, price is now $1,196 per person
$1,196
per person
Oct 1 - Oct 6
found 8 hours ago
Roundtrip flight included
Houston (HOU) to Springfield (VSF)
8.8/10 Excellent! (26 reviews)
The place was not cleaned well. The water was off we had to call the front desk. The Diswasher was fully of dishes. There was only one roll of toilet paper in the bathroom. No paper towel in the kitchen, not even one to start. The wall in the kitchen was dirty

Reviewed on Dec 1, 2025

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Stay near popular Hinsdale attractions

Hinsdale Public Library

The Hinsdale Public Library serves as a community hub with diverse resources and engaging programs. Browse their curated collection or join a workshop to experience authentic small-town New Hampshire culture.
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Hinsdale Hotel Deals

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

Hinsdale NH
$173 nightly
The price is $188 total per night from Jul 19 to Jul 20
$188 total
Jul 19 - Jul 20
Total with taxes and fees
10/10 Exceptional! (15 reviews)
"Very enjoyable getaway weekend!!"

Reviewed on Jul 12, 2026

RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $146 total per night from Jul 19 to Jul 20
$146 total
Jul 19 - Jul 20
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
"We had a great stay overall. The hotel was clean, well-maintained, and the staff was friendly, welcoming, and courteous throughout our visit. Breakfast was good, but the pancake station became backed up during the busy morning rush. Adding a second pancake machine would help reduce the wait and make ..."

Reviewed on Jul 14, 2026

Keene Elm City Hotel, an Ascend Collection Hotel
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St Keene NH
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $151 total per night from Jul 19 to Jul 20
$151 total
Jul 19 - Jul 20
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
"Nice place. Was a great to have a stop."

Reviewed on Jul 16, 2026

Best Western Plus Keene Hotel
See all 982 properties in Hinsdale
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 Hinsdale Vacation Packages

Hinsdale Essential Information

Language
English
Currency
U.S dollars
Population
1,550

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Frequently asked questions

How much does a Hinsdale vacation package cost?
You can grab a vacation package to this destination from $780 on Expedia. But how much your vacation to Hinsdale costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Hinsdale?
January, October and December are great times to search for cheap Hinsdale vacation packages. Opting to travel in less busy periods means you can usually find reduced prices on accommodations and flights.
How many days is enough for Hinsdale?
Usually, a handful of days is enough to see the major sights during your Hinsdale vacation. But if you'd like to have more time to unwind or take day tours, think about extending your itinerary.
How to find the best Hinsdale package deals?
Begin your search for a Hinsdale package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Hinsdale package deal right away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Hinsdale escape underway.
Is it cheaper to book a Hinsdale vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component separately. And you'll still have the flexibility to create a tailored Hinsdale vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Hinsdale?
If you're considering a spur-of-the-moment Hinsdale adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Hinsdale vacation packages?
If you're anything like us, you love going away but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Hinsdale vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.

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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.