Winchester Holiday Packages

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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$252 per night from 17 Jan to 18 Jan
AU$252
includes taxes & fees
17 Jan - 18 Jan
The Colonial Hotel: Pet-friendly hotel with free WiFi and free parking. Located near skiing.
"Great stay and service."

Reviewed on 8 Jan. 2025

The Colonial Hotel
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 AU$179 per night from 28 Jan to 29 Jan
AU$179
includes taxes & fees
28 Jan - 29 Jan
Hampton Inn Brattleboro: Pet-friendly hotel with free breakfast and free WiFi. Located near skiing.
"The hotel was clean and staff were helpful. The breakfast was better than average and they have 24 hours hot coffee and tea. The pool and hot tub were closed which was a disappointment. A pipe burst in our bathroom in the middle of the night, but the staff were quick to get us a new room and were ..."

Reviewed on 4 Jan. 2025

Hampton Inn Brattleboro
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$174 per night from 12 Jan to 13 Jan
AU$174
includes taxes & fees
12 Jan - 13 Jan
Colonial Motel And Spa: Pet-friendly motel with free WiFi and free parking. Located near skiing.
Great for a couple of guys for an overnight snowbo
"I I would happily stay there again."

Reviewed on 9 Jan. 2025

Colonial Motel And Spa
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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.