Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

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
The price is 3.574.603 ₫ per night from 9 Mar to 10 Mar
3.574.603 ₫
3.992.831 ₫ total
includes taxes & fees
9 Mar - 10 Mar
8.6/10 Excellent! (1,003 reviews)
"Really neat Hotel... only a few things need to work on, breakfast everyday, little things to tighten up in rooms (sink drain not working, when redoing caulking have someone take time and make neat.. presentation is everything. Would defiantly stay again..."

Reviewed on 27 Feb 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 2.784.078 ₫ per night from 6 Mar to 7 Mar
2.784.078 ₫
3.062.486 ₫ total
includes taxes & fees
6 Mar - 7 Mar
6.6/10 (1,001 reviews)
Kindness
"Thank you. Man behind counter was very professional."

Reviewed on 23 Feb 2025

Colonial Motel And Spa
Comfort Inn & Suites Brattleboro I-91
Comfort Inn & Suites Brattleboro I-91
2.5 out of 5
1186 Putney Road, Brattleboro, VT
Fully refundableReserve now, pay when you stay
The price is 2.714.153 ₫ per night from 4 Mar to 5 Mar
2.714.153 ₫
2.985.569 ₫ total
includes taxes & fees
4 Mar - 5 Mar
8.6/10 Excellent! (595 reviews)
Nice
"The hotel staff is efficient and friendly. The room we stayed has non-working drain stoppers in sink and bathtub. But it’s ok for us. Overall the room is comfortable, window A/c is quiet and breakfast is free with basics. It’s 1 min walk to a chain restaurant which we also find convenient."

Reviewed on 21 Feb 2025

Comfort Inn & Suites Brattleboro I-91
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.