Winchester Vacations from $294

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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 Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $374, price is now $294 per person
$294
per person
Feb 13 - Feb 15
found 1 day ago
Roundtrip flight included
New York (NYC) to Springfield (VSF)
7.6/10 Good! (1,002 reviews)
The staff was by the staff I mean the one person I saw who checked me. The property is very dated There were mattresses in the stairwell in a very interesting clientele that seemed to linger in the hallways and around the building at all hours of the night The room was fine Nothing to write home about. What was disappointing was the $350 a night that this place charged Granted it was during Leaf season which I was unaware of when made the reservation but in general the facility was tired

Reviewed on Dec 30, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $973, price is now $764 per person
$764
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
8.8/10 Excellent! (881 reviews)
Room was clean, a little tired Great view of river and Billings Farm

Reviewed on Jan 5, 2026

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,427, price is now $1,128 per person
$1,128
per person
Mar 17 - Mar 22
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Clean, staff was great.

Reviewed on Dec 23, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,687, price is now $1,376 per person
$1,376
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Springfield (VSF)
9.2/10 Wonderful! (549 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Save 100% on your flight
Price was $2,189, price is now $1,795 per person
$1,795
per person
Feb 12 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Springfield (VSF)
8.8/10 Excellent! (242 reviews)
Ski slopes were accessible and pool was really nice.

Reviewed on Dec 27, 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
$160 nightly
The price is $179 total per night from Jan 11 to Jan 12
$179 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,005 reviews)
Friendly stadd

Reviewed on Dec 25, 2025

The Colonial Hotel
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
1186 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $136 total per night from Jan 11 to Jan 12
$136 total
Jan 11 - Jan 12
Total with taxes and fees
8.4/10 Very Good! (753 reviews)
The room was clean and the staff was wonderful

Reviewed on Jan 2, 2026

Comfort Inn & Suites Brattleboro I-91
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
1043 Putney Road Brattleboro VT
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Jan 11 to Jan 12
$93 total
Jan 11 - Jan 12
Total with taxes and fees
7.6/10 Good! (1,003 reviews)
Front Desk boy was super cute, but no breakfast served. Very quiet for being such a busy street.

Reviewed on Dec 21, 2025

The Covered Bridge Inn
See all 455 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 $294 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.