Chester Holiday Packages

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Many travellers see savings of up to . Also, you'll be able to mix and match from more than 550 airlines and 665,000 properties.

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Chester Accommodation

You'll need to act fast if you want to book accommodations in Chester. There are only 5 properties in the surrounding area.

Supposed to have organised somewhere to stay by now? Left it to the last minute? No need to stress — we've got you covered. Try out the Inn Victoria (321 Main St) or the Chester House Inn (266 Main St).

Car Hire in Chester

If you were thinking about renting a set of wheels right at Rutland Southern Vermont Regional Airport, you'll have to think twice. But don't panic! Climb into a cab, make the quick trip to Enterprise (131 S Main Street) and you'll be holding the keys to a rental car soon enough.

Holidays to Chester

Forgot that day in class when you were taught some basic info about Chester? There's no need to have a tanty over your lack of geography skills — we'll let you in on the essentials.

Chester is not far from a couple of significant cities. You can get to this town from Claremont, which is 25 kilometres away to the northeast. Keene is also just 45 kilometres to the southeast.

If you're into knowing bits of trivia about the place you're travelling to, you might be interested to hear that the population of this part of Central Vermont- Killington is around 3 000.

Top Chester hotels

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is AU$621 per night from 15 Dec to 16 Dec
AU$621
15 Dec - 16 Dec
includes taxes & fees
Woodstock Inn & Resort: Luxury resort with free WiFi and free valet parking. Located in the city centre.
I’ve traveled a lot around the world and this hotel has to be in my top 3 ever. Especially beautiful in autumn

Reviewed on 4 Nov 2025

Opens in a new windowWoodstock Inn & Resort
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
The price is AU$313 per night from 17 Nov to 18 Nov
AU$313
17 Nov - 18 Nov
includes taxes & fees
Kimpton Taconic Hotel by IHG: Pet-friendly hotel with outdoor pool and a bar/lounge. Located in a state park.
No continental breakfast ,no microwave or in room coffeemaker. Only water or iced tea at check in , no coffee

Reviewed on 25 Oct 2025

Opens in a new windowKimpton Taconic Hotel by IHG
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
The Shire Woodstock: Pet-friendly hotel with free WiFi and free parking. Located in the mountains.
Great place to stay

Reviewed on 3 Nov 2025

Opens in a new windowThe Shire Woodstock
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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.