Winchester Vacations from $491

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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.
Deerfield Valley Inn

Deerfield Valley Inn

2 out of 5
Price was $589, price is now $491 per person
$491
per person
Aug 7 - Aug 13
found 12 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Springfield (VSF)
9.4/10 Exceptional! (118 reviews)
Way overpriced . I’ve stayed in other hotels in the area that included breakfast with hot tubs that are 50% less than this place. The place to put your shoes in the room had mud all over it. Maybe clean it before your next guest.

Reviewed on Mar 2, 2026

Chalet 239

Chalet 239

2 out of 5
Price was $692, price is now $505 per person
$505
per person
Aug 7 - Aug 13
found 12 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Springfield (VSF)
9.4/10 Exceptional! (125 reviews)
Staff very helpful. Everything was very clean

Reviewed on May 17, 2026

Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
Price was $757, price is now $584 per person
$584
per person
Aug 7 - Aug 13
found 12 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Springfield (VSF)
8.6/10 Excellent! (268 reviews)
Rooms were very clean, great coffee in the room. The resort(the actual area in general )is in “mud month”. Very few restaurants and stores were open. Not the fault of the resort. Refrigerator needed to be requested. The views were spectacular and the lobby was beautiful

Reviewed on May 2, 2026

Mount Snow Lodging by Vail Resorts

Mount Snow Lodging by Vail Resorts

3 out of 5
Price was $846, price is now $669 per person
$669
per person
Aug 7 - Aug 13
found 12 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Springfield (VSF)
7.8/10 Good! (23 reviews)
The room hotel was very nice. The parking lot was very icy and snowy and the indoor hot tub had a lot of chlorine odor coming from it so we couldn't use that because we had a baby and it was too much smelling like chlorine. Great location though to go skiing

Reviewed on Apr 9, 2025

Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,210, price is now $1,009 per person
$1,009
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Springfield (VSF)
10/10 Exceptional! (113 reviews)
Convenient location with food, brewery, & park nearby. Close to Burlington yet away from the crowds. Breakfast buffet was varied and very good. Common areas have a chill vibe. Host was welcoming. Place was super clean. Bed was comfortable. Would like to visit again with more time to explore the area.

Reviewed on May 9, 2026

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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 May 27 to May 28
$179 total
May 27 - May 28
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
"One suggestion would be to have coffee and tea available in the lobby. Other than that it was a nice stay."

Reviewed on May 25, 2026

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
$122 nightly
The price is $134 total per night from Jun 7 to Jun 8
$134 total
Jun 7 - Jun 8
Total with taxes and fees
8.2/10 Very Good! (983 reviews)
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Reviewed on May 26, 2026

Hampton Inn Brattleboro
Latchis Hotel

Latchis Hotel

2.5 out of 5
50 Main Street Brattleboro VT
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $126 total per night from May 27 to May 28
$126 total
May 27 - May 28
Total with taxes and fees
8.6/10 Excellent! (885 reviews)
"The staff was great very helpful!!! Very understanding and had patience with me. Thanks Peace&patience JRC"

Reviewed on May 25, 2026

Latchis Hotel
See all 466 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 $491 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.