Winchester Vacations

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Your Winchester Vacation

Unforgettable adventures await when you lock in a Winchester vacation package. Whether you're a foodie, art enthusiast or just a traveler who loves discovering new places, there's something for everyone in this interesting city. Fill your trip to Winchester with tours of some of its big-hitting attractions. Where to first? Don't miss Pisgah State Park. No matter your travel plans or budget, organizing a tailored Winchester vacation is easy with Expedia.

Winchester Essential Information

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

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 $160 per night from May 29 to May 30
$160
$175 total
includes taxes & fees
May 29 - May 30
8.4/10 Very Good! (832 reviews)
"We had a pleasant stay at The Colonial. It was relatively close to Game On in Fitchburg, where my daughter had a basketball tournament. It is a outdated, but very clean. The only negatives were they provided our room with minuscule size bottles of shampoo and conditioner, so we had to ask for more. ..."

Reviewed on May 12, 2024

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 $98 per night from May 27 to May 28
$98
$108 total
includes taxes & fees
May 27 - May 28
6.8/10 (1,000 reviews)
"Great pool and hot tub facilities with kickers"

Reviewed on May 19, 2024

Colonial Motel And Spa
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
The price is $76 per night from Jun 7 to Jun 8
$76
$85 total
includes taxes & fees
Jun 7 - Jun 8
8.2/10 Very Good! (1,000 reviews)
"The room was quiet and clean. The staff was friendly. I would stay there again."

Reviewed on May 20, 2024

The Covered Bridge Inn
See all 373 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
Our Winchester packages, which start at just , are an easy way to save precious money. Pick your preferred hotels, flights and more to create a personalized getaway.
How do I get a cheap travel package to Winchester?
Bundle your hotels and flights with Expedia to save big on your next big adventure. With more than 550 airlines and 1,000,000 properties globally, your Winchester vacation package can be tailored exactly to suit your travel style. With all that extra money, why not throw in one or more fun activities and tours? It’s an easy way to unlock even more bargains. The vacation you’ve always dreamed of in Winchester is closer than you thought!
What are the top hotels in Winchester?
Stay At A Craft Brewery In Winchester Nh Close To Mountains and Magical Lakefront Home In Forest Lake are among the most well-known hotels in Winchester. Why not look up the rates and amenities at each and then make up your mind?
How far in advance should I book my Winchester vacation?
Your safest bet is to book early. Airlines generally advertise flight tickets nearly 12 months prior to departure, and this is an ideal opportunity to pick up some of the cheapest prices. Just been told you need to take all your vacation days in a few weeks? No problem! Expedia are never short on fantastic bargains to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Winchester travel package include?
Hotels, flights and rental cars — we have them covered. With Expedia, you can create your Winchester travel package just how you like it. All you have to do is decide exactly what you need. Once you’ve made your booking, you can add extras like activities and experiences. The more you bundle, the greater the savings!
What should I know before booking a Winchester travel package?
An Expedia travel package can be customized for your circumstances and is an easy way to stretch your hard-earned dollars. How little or much you include is your call. Rental cars, hotels and flights — mix and match whatever combination works with your plans.
Can I choose my airline with a Winchester Expedia vacation package?
Yes — that’s the beauty of an Expedia package. You get to decide. We have more than 550 partner airlines throughout the world, so you have lots of choice when arranging your Winchester escape.
If I'm not able to travel, can I cancel my Winchester vacation package?
Don’t stress if you’re rethinking your Winchester vacation package — it’s possible to change or amend your booking. And if you’ve booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We get that life can throw the occasional spanner in the works, so look up our Customer Service Portal if that occurs. When you’re ready to make changes, we’re here to help.

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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.