Winchester Vacations from $351

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Your Winchester Vacation

When a city stay is calling, answer it with a vacation package to Winchester. With all your travel needs organized before you leave, all you need to do here is focus on having a ball. If a sightseeing tour is on the to-do list during your trip to Winchester, look around leading attractions like Thomas Aquinas College, Pisgah State Park and Birch Point. Stop dreaming and start adventuring. Explore the broad range of options on Expedia today and put your Winchester vacation plans into motion!

The Latest Winchester 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 $443, price is now $351 per person
$351
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
17.6/10 Exceptional! (881 reviews)
Large, clean room with nice view. Unique.

Reviewed on Nov 9, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $765, price is now $671 per person
$671
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
17.2/10 Exceptional! (834 reviews)
Room was very clean and comfortable. Loved having the fireplace. Indoor parking garage was a plus with easy access to our room. We enjoyed dinner and breakfast at the restaurant. The outdoor space was fabulous with many activities.

Reviewed on Nov 14, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $817, price is now $764 per person
$764
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
18.4/10 Exceptional! (549 reviews)
Clean room, Awesome staff and always a good vibe.

Reviewed on Nov 17, 2025

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $538, price is now $517 per person
$517
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Springfield (VSF)
20/10 Exceptional! (105 reviews)
Highly recommend staying here. I will stay here again if I’m ever planning to return to Vermont. The customer service is top notch and we really enjoyed the locally sourced homemade breakfast too. Everything was a dreamy bed and breakfast.

Reviewed on Nov 2, 2025

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Winchester Hotel Deals

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road Gardner MA
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $177 total per night from Dec 1 to Dec 2
$177 total
Dec 1 - Dec 2
Total with taxes and fees
8.8/10 Excellent! (1,002 reviews)
Very nice hotel.

Reviewed on Nov 13, 2025

The Colonial Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $158 total per night from Nov 30 to Dec 1
$158 total
Nov 30 - Dec 1
Total with taxes and fees
8.2/10 Very Good! (919 reviews)
A used bar of soap was left in the shower with hairs on it.

Reviewed on Nov 13, 2025

Hampton Inn Brattleboro
Hampton Inn & Suites Greenfield

Hampton Inn & Suites Greenfield

2.5 out of 5
184 Shelburne Rd Greenfield MA
Fully refundableReserve now, pay when you stay
$183 nightly
The price is $205 total per night from Nov 30 to Dec 1
$205 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (873 reviews)
Check in was great!

Reviewed on Nov 13, 2025

Hampton Inn & Suites Greenfield
See all 440 properties in Winchester
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 Winchester Vacation Packages

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
1,750
Top Sights
Colonial Theatre, Pisgah State Park and Cheshire Childrens Museum

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $351 on Expedia for your Winchester escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
If you're looking to snag a cheap Winchester vacation package, consider traveling in October, November and December. You'll usually find better rates on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Winchester?
Usually, a handful of days is enough to go to the top sights during your Winchester vacation. But if you prefer to have some time to unwind or go on day trips, think about extending your trip.
How to find the best Winchester package deals?
Finding a cheap Winchester package deal is easy with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, apply a few filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Winchester package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Winchester vacation as a package?
You can enjoy significant savings on your next Winchester break by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Winchester?
If you've got your Winchester vacation dates finalized, book early to bag some unbeatable deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
If you're 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've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Winchester break over 3, 6 or 12 months. There are also no late payment fees or hidden costs, 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.