
Book Exclusive Chester Vacation Packages
Chester flight + hotel packages
Price found within the past 48 hours. Click for updated prices.

Mountaineer Inn
per person
May 4 - May 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Springfield (VSF)
Stay at this motel in West Dover. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mount Snow and Heavy Metal Ski Lift are located nearby.


Mount Snow Lodging
per person
May 4 - May 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Springfield (VSF)
Stay at this 3-star ski hotel in West Dover. Enjoy free WiFi, free parking, and ski-in/ski-out access. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.

Mount Snow Grand Summit Resort
per person
May 4 - May 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Springfield (VSF)
Stay at this 3-star spa resort in West Dover. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Mount Snow and Ego Alley Ski Lift are located nearby.
Top Chester hotels deals

Fullerton Inn
40 The Common, Chester, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $185 per night
CA $185
CA $201 total
includes taxes & fees
27 Mar - 28 Mar
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions DaVallia Art & Accents and Bonnie's Bundles Dolls are located nearby.
Breakfast included
Parking included

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Stay at this cabin in Chester. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Kitchen
Pet-friendly

Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is CA $428 per night
CA $428
CA $534 total
includes taxes & fees
23 Mar - 24 Mar
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Woodstock Town Hall Theatre and Red Wagon Toy Company are located nearby.
Pool
Hot tub

Holiday Inn Club Vacations Mount Ascutney Resort by IHG
485 Hotel Road, Brownsville, VT
Free cancellation
The price is CA $170 per night
CA $170
CA $205 total
includes taxes & fees
30 Mar - 31 Mar
Stay at this 3-star resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our reviews. Popular attractions Mount Ascutney and Mt Ascutney State Park are located nearby.
Pool
Restaurant

Colonial Motel And Spa
889 Putney Rd, Brattleboro, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $156 per night
CA $156
CA $172 total
includes taxes & fees
31 Mar - 1 Apr
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and United States Navy Seabee Bridge are located nearby.
Pool
Hot tub

Hampton Inn and Suites Manchester
4519 Main St, Manchester Center, VT
Free cancellation
Reserve now, pay when you stay
The price is CA $194 per night
CA $194
CA $213 total
includes taxes & fees
22 Apr - 23 Apr
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Manchester Designer Outlets and American Museum of Fly Fishing are located nearby.
Pool
Hot tub
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.
Popular places to visit
Bonnie's Bundles Dolls
Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views, or seek out its ski slopes.
DaVallia Art & Accents
Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.
Chester Vacations
Got your plane ticket booked and your luggage zipped up? Read on for a few basic Chester tips before you jet off.
This town lies 15 miles (24 kilometers) southwest of Claremont. It is also 30 miles (48 kilometers) northwest of Keene.
It shouldn't be too hard to make new acquaintances in this part of Central Vermont- Killington. It has a population of 3,000 locals.
Places to visit in Chester
Few things are as exciting as gazing out at a blanket of powder snow and knowing you've got the whole day in front of you to have fun on the slopes. Grab your beanie and put on your skis — Okemo Mountain Resort awaits! After more ideas? Whether you're an ace on the snow or a newbie, it's time to get out your snowboard and barrel down the slopes. Magic Mountain Ski Resort promises heaps of fun for every skill level! And, there's still more going on in the surrounding area. Whether you're a master on the snow or a rookie, it's time to dust off your snowboard and tackle the slopes. Grafton Ponds Outdoor Center guarantees plenty of fun for all skill levels!Where do you fly into for Chester?
Get ready for some incredible new experiences! The middle of Chester is only 25 miles (40 kilometers) southeast of Rutland Southern Vermont Regional Airport (RUT).Frequently asked questions
Photos of local treasures
Browse Chester vacation photos for more inspiration
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