Chester

Travel Guide

Where to stay in Chester

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Chester Depot

If you're spending some time in Chester Depot, Bonnie's Bundles Dolls and DaVallia Art & Accents are top sights worth seeing.

Chester Depot
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is €350 per night from 30 Nov to 1 Dec
€350
30 Nov - 1 Dec
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 ...
9.2/10 Wonderful! (549 reviews)
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

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Stay at this hotel in Woodstock. Enjoy free Wi-Fi, free parking and free bicycles on-site. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8.6/10 Excellent! (879 reviews)
Large, clean room with nice view. Unique.

Reviewed on 9 Nov 2025

The Shire Woodstock
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
The price is €184 per night from 1 Dec to 2 Dec
€184
1 Dec - 2 Dec
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 ...
9.2/10 Wonderful! (813 reviews)
No continental breakfast ,no microwave or in room coffeemaker. Only water or iced tea at check in , no coffee

Reviewed on 25 Oct 2025

Kimpton Taconic Hotel by IHG
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.
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 ...
9.8/10 Exceptional! (23 reviews)
Hidden gem!
This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!

Reviewed on 24 Feb 2025

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3 out of 5
3387 East Mountain Road Killington VT
Stay at this ski cabin in Killington. Enjoy free Wi-Fi, free parking and a sauna. Popular attractions Killington Resort and Pico Mountain at Killington Ski Resort ...
9/10 Wonderful! (53 reviews)
Arrived after dark. Didn’t know where to park. Very secluded. Outside light would not stay lit. Upstairs needs attention.

Reviewed on 27 Oct 2025

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

3 out of 5
761 Stratton Access Rd Stratton VT
Stay at this ski aparthotel in Stratton. Enjoy free Wi-Fi, free parking and 10 restaurants. Popular attractions Stratton Mountain Resort and Villager Ski Lift ...
8.4/10 Very Good! (77 reviews)
Nice lodge. Room needs updating

Reviewed on 19 Oct 2025

Long Trail House at Stratton Mountain Resort
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.

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