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

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is NZ$639 per night from 22 Feb to 23 Feb
NZ$639
22 Feb - 23 Feb
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 ...
Excellent hotel, staff well trained.

Reviewed on 21 Jan 2026

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
The price is NZ$377 per night from 3 Mar to 4 Mar
NZ$377
3 Mar - 4 Mar
includes taxes & fees
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge) and room service. Our guests praise the helpful staff and the property ...
Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return!

Reviewed on 4 Jan 2026

Opens in a new windowKimpton Taconic Hotel by IHG
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
The price is NZ$256 per night from 1 Mar to 2 Mar
NZ$256
1 Mar - 2 Mar
includes taxes & fees
Stay at this spa hotel in Cavendish. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the helpful staff and the clean rooms in their ...
Friendly staff, clean rooms.

Reviewed on 28 Jan 2026

Opens in a new windowPointe at Castle Hill Resort
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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.