Chester Holiday Packages

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Chester Accommodation

You'll need to act fast if you want to book accommodation 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

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Chester VT
Stay at this cabin in Chester. Enjoy free Wi-Fi, an in-room coffee maker and in-room fireplaces. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial ...
"I had a great stay! Everything was as shown and described in the listing. My only advice is-if you are staying there during mud season make sure you have a AWD/4WD vehicle-the road to the property can get pretty bad."

Reviewed on 11 Mar 2026

Opens in a new windowLuxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is NZ$934 per night from 28 June to 29 June
NZ$934
28 June - 29 June
includes taxes & fees
Stay at this luxury resort in Woodstock. Enjoy free Wi-Fi, free valet parking and an outdoor pool. Our guests praise the helpful staff in their reviews. Popular ...
"Had a short stay with my family to the Woodstock Inn and would love to return some day. Hospitality at its best in a beautiful town. The grounds and amenities were immaculate and authentic to the area. A memorable stay."

Reviewed on 25 June 2026

Opens in a new windowWoodstock Inn & 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 NZ$288 per night from 30 June to 1 July
NZ$288
30 June - 1 July
includes taxes & fees
Stay at this inn in Chester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms in their reviews. Popular ...
"We had a wonderful weekend. Inn is a little dated but very cute. Room was clean and we sat out on our balcony with wine at night and coffee in the morning. Needed a dusting but comfortable. I would stay there again and recommend it to those traveling. Great location."

Reviewed on 21 June 2026

Opens in a new windowFullerton Inn
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