Winchester Holidays

Photo by Donny Campos
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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

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! (1,005 reviews)
"This Hotel is like an Old Family Friend. It’s our go to when we are staying in the area. Friendly staff. Comfortable rooms."

Reviewed on 5 Jul, 2025

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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 S$137 per night from 10 Jul to 11 Jul
S$137
10 Jul - 11 Jul
includes taxes & fees
6.6/10 (1,002 reviews)
"We like the room. Nice and spacious. Er"

Reviewed on 2 Jul, 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 S$178 per night from 20 Jul to 21 Jul
S$178
20 Jul - 21 Jul
includes taxes & fees
8/10 Very Good! (841 reviews)
"Great for the price"

Reviewed on 28 Jun, 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 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.