Winchester Holiday Packages

Save when you book Winchester package deals

Choose two or more items and save on your trip:

Book your Winchester holiday

Wotif can help you save some cash!

We can bundle your flights and hotels into one simple package. Talk about convenience!

With your extra cash, the possibilities are endless in Winchester.

Book now and save up to . And don't forget, we can link you up with more than 550 partner airlines and 665,000 properties — your perfect holiday is only a couple of clicks away.

Wotif has some of the most competitive deals online. Better start packing your bags — now's the perfect time for a new adventure.

Winchester Accommodation

The Centennial House is the only listed property in Winchester. Book now and nab the best room.

Car Hire in Winchester

Enterprise is the nearest car rental outlet to Dillant-Hopkins Airport. Just take a taxi to 535 Main Street, and you'll be driving off into the sunset in no time.

Holidays to Winchester

Don't be that traveller wandering around Winchester not knowing where you're going. Get to know a few details about this exciting destination before you head off.

Winchester is just down the road from some major cities that'll help you get your bearings. Just 17 kilometres to the northwest is Brattleboro. The town isn't too far from Keene either. You only need to travel northeast for 20 kilometres before you reach it.

If you're travelling with the young ones and they're starting to get restless, why not quiz them to see if they know what the population of this part of New Hampshire is? (It's around about 2 000 in case you weren't too sure yourself.)

Top Winchester hotels

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 AU$246 per night from 24 Feb to 25 Feb
AU$246
includes taxes & fees
24 Feb - 25 Feb
The Colonial Hotel: Pet-friendly hotel with free WiFi and free parking. Located near skiing.
"This Hotel was much better then I expected. It’s beautiful, clean, staff is super attentive and friendly. Hotel is big and room as comfortable. My family and I had a great time. Highly recommend. If we ever go back to Massachusetts we will definitely stay at The Colonial Hotel again."

Reviewed on 21 Feb. 2025

The Colonial Hotel
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 AU$184 per night from 3 Mar to 4 Mar
AU$184
includes taxes & fees
3 Mar - 4 Mar
Comfort Inn & Suites Brattleboro I-91: Business-friendly hotel with free breakfast and free WiFi. Located near ski lifts.
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
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 AU$189 per night from 24 Feb to 25 Feb
AU$189
includes taxes & fees
24 Feb - 25 Feb
Colonial Motel And Spa: Pet-friendly motel with free WiFi and free parking. Located near ski runs.
"All ok everything worked well just older decor"

Reviewed on 10 Feb. 2025

Colonial Motel And Spa
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.