Winchester Vacations

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    Save up to ₩234,741 when you book a flight and hotel together*
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Find the Best Winchester Vacation Packages

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
The price is ₩198,514 per night from Aug 17 to Aug 18
₩198,514
₩221,751 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Stayed here years ago. The rooms haven't changed much. The rooms are pretty standard, but the lobby, staff and food are all better than most hotels. Maybe a little old school, but I love the look of the hotel. The bed was really comfortable. The event banquet food has always been wonderful. They ..."

Reviewed on Aug 12, 2025

The Colonial Hotel
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is ₩193,067 per night from Aug 17 to Aug 18
₩193,067
₩212,374 total
Aug 17 - Aug 18
includes taxes & fees
6.6/10 (1,003 reviews)
"The room I was given was quite impressive in size. Plenty accommodating for me and my dog. The a/c worked well, fridge was plenty cold, bed was comfortable and clean, the grounds surrounding the buildings is very nice for traveling with a dog. The front desk help was gracious and accommodating. That ..."

Reviewed on Aug 9, 2025

Colonial Motel And Spa
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is ₩167,624 per night from Sep 4 to Sep 5
₩167,624
₩184,386 total
Sep 4 - Sep 5
includes taxes & fees
8/10 Very Good! (864 reviews)
Nice hotel option in Southern Vermont
"Great hotel to stay when traveling in Vermont. Convenient - right off of I-91, centrally located to a number of restaurants and food options. Pet-friendly hotel, we brought our furry friend and he was comfortable. Amenities were nice and clean including the pool and fitness area. Friendly staff who ..."

Reviewed on Aug 12, 2025

Hampton Inn Brattleboro
See all 414 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.

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices 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?
To score cheap Winchester vacation packages, organize your getaway outside of peak periods like public holidays and major events. You'll generally find lower prices and better availability for flights and hotels.
How many days is enough for Winchester?
The ideal length of your Winchester vacation depends on what you'd like to do and see. Generally, a few days to a week will give you plenty of time to tick off all the major sights and explore some hidden spots along the way.
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.
How to plan a trip to Winchester?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Winchester.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to flights and experiences. Your accommodations will probably be the biggest expense during your trip to Winchester.
  3. Decide how long to go for: Now that you're up to speed on Winchester, you can work out the perfect length of your vacation. Put together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your airfare and accommodations: Once you've nailed down your dates and duration, book the ideal Winchester vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.