Winchester Holidays

Photo by Donny Campos

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Top hotels in Winchester

The Colonial Hotel

The Colonial Hotel

3 out of 5
625 Betty Spring Road, Gardner, MA
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,001 reviews)
"This is a greag property with plenty of historic charm. The staff are all friendly and helpful. This was my second stay here and I'll definitely be back."

Reviewed on 17 Aug 2025

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The Colonial Hotel
Keene Elm City Hotel, Ascend Hotel Collection

Keene Elm City Hotel, Ascend Hotel Collection

2.5 out of 5
175 Key Rd, Keene, NH
Fully refundableReserve now, pay when you stay
The price is €116 per night from 31 Aug to 1 Sept
€116
31 Aug - 1 Sept
includes taxes & fees
8.4/10 Very Good! (881 reviews)
"Had a great time at this location"

Reviewed on 19 Aug 2025

Keene Elm City Hotel, Ascend Hotel Collection
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 €131 per night from 25 Aug to 26 Aug
€131
25 Aug - 26 Aug
includes taxes & fees
6.6/10 (1,003 reviews)
"Appears to house a lot of homeless."

Reviewed on 22 Aug 2025

Colonial Motel And Spa
See all 410 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 holiday 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 holiday to Winchester costs.
What are the cheapest months to go to Winchester?
To score cheap Winchester holiday packages, organise 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 holiday 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 personalise 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 travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Winchester holiday as a package?
You can enjoy significant savings on your next Winchester break by booking a customised holiday 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 holiday package to Winchester?
If you've got your Winchester holiday 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 travelling 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 accommodation 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 holiday. Put together a draft itinerary and allocate enough time to cover everything you want to do.
  4. Combine your airfare and accommodation: Once you've nailed down your dates and duration, book the ideal Winchester holiday package for you.

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