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$543 per night from 8 Mar to 9 Mar
AU$543
8 Mar - 9 Mar
includes taxes & fees
Woodstock Inn & Resort: Luxury resort with free WiFi and free valet parking. Located near skiing.
Excellent hotel, staff well trained.

Reviewed on 21 Jan 2026

Opens in a new windowWoodstock Inn & Resort
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
The price is AU$234 per night from 1 Mar to 2 Mar
AU$234
1 Mar - 2 Mar
includes taxes & fees
Pointe at Castle Hill Resort: Business-friendly hotel with free WiFi and free parking. Located near ski lifts.
The Pointe was much more than I expected (honestly). The room was large with a couch, reading chair (and ottoman) and small table and 2 chairs. The bathroom had a tub with jets. There was an indoor pool and hot tub-that worked. The one negative, no microwave in the room or common area— but the desk ...

Reviewed on 16 Feb 2026

Opens in a new windowPointe at Castle Hill Resort
Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
The price is AU$199 per night from 1 Mar to 2 Mar
AU$199
1 Mar - 2 Mar
includes taxes & fees
Fullerton Inn: Inn with free breakfast and free WiFi. Located near skiing.
Friendliness, ease of checkin and iut

Reviewed on 14 Feb 2026

Opens in a new windowFullerton Inn
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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.