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$244 per night from 6 Apr to 7 Apr
AU$244
includes taxes & fees
6 Apr - 7 Apr
The Colonial Hotel: Pet-friendly hotel with free WiFi and free parking. Located near skiing.
The colonial hotel
"Room was very clean and the bed was really comfortable. Front desk personnel were very attentive and friendly. All of this made for a great overnight stay. I stayed there last December and will definitely stay again in the future!"

Reviewed on 30 Mar. 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$188 per night from 28 Apr to 29 Apr
AU$188
includes taxes & fees
28 Apr - 29 Apr
Hampton Inn Brattleboro: Pet-friendly hotel with free breakfast and free WiFi. Located near skiing.
"Booked hotel 10 weeks before the stay specifically so I could use the pool and hot tub for my health condition. 4 days before arriving (1 day AFTER penalty free cancellation), I noticed they posted on their web site the pool & hot tub would be closed for the next 4 weeks (starting a few week before ..."

Reviewed on 29 Mar. 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$191 per night from 6 Apr to 7 Apr
AU$191
includes taxes & fees
6 Apr - 7 Apr
Colonial Motel And Spa: Pet-friendly motel with free WiFi and free parking. Located in the city centre.
"Very nice clean and convenient accommodations"

Reviewed on 30 Mar. 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.