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Chester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Doveberry Inn

Doveberry Inn

2 out of 5
Price was CA $1,170, price is now CA $1,157 per person
CA $1,157
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Stay at this B&B in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Nitro Express Ski Lift are located nearby.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,452, price is now CA $1,368 per person
CA $1,368
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Stay at this hotel in Brattleboro. Enjoy free WiFi, free parking, and conference space. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Latchis Theatre and Brattleboro Museum & Art Center are located nearby.
1846 Inn and Tavern

1846 Inn and Tavern

3 out of 5
Price was CA $1,387, price is now CA $1,322 per person
CA $1,322
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Stay at this inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was CA $1,225, price is now CA $1,186 per person
CA $1,186
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Colonial Motel

Colonial Motel

3 out of 5
Price was CA $1,179, price is now CA $1,157 per person
CA $1,157
per person
Oct 30 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Book a stay at this business-friendly motel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Brattleboro Bowl and New England Center for Circus Arts are located nearby.

Top Chester hotels deals

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
Free cancellation
Reserve now, pay when you stay
The price is CA $225 per night
CA $225
CA $245 total
Oct 18 - Oct 19
includes taxes & fees
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
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
698 VT-11 Chester VT
Free cancellation
Reserve now, pay when you stay
The price is CA $367 per night
CA $367
CA $400 total
Sep 29 - Sep 30
includes taxes & fees
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located nearby.
Breakfast included
Parking included
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
Get rates
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.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $946 per night
CA $946
CA $1,103 total
Oct 27 - Oct 28
includes taxes & fees
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 Middle Covered Bridge and Woodstock Town Hall Theatre are located nearby.
Pool
Hot tub
The Jackson

The Jackson

4 out of 5
43 Senior Lane Woodstock VT
The price is CA $334 per night
CA $334
CA $367 total
Oct 26 - Oct 27
includes taxes & fees
Stay at this B&B in Woodstock. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast in our reviews. Popular attractions Union Arena Community Center and Five Elm Arches are located nearby.
Parking included
Free WiFi
Grand Summit Resort, A Vail Resorts Property

Grand Summit Resort, A Vail Resorts Property

3 out of 5
89 Grand Summit Way West Dover VT
Free cancellation
The price is CA $212 per night
CA $212
CA $254 total
Oct 28 - Oct 29
includes taxes & fees
Book a stay at this spa resort in West Dover. Enjoy free WiFi, a full-service spa, and a free area shuttle. Popular attractions Mount Snow and Tumbleweed Ski Lift are located nearby.
Spa
Free WiFi
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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.

Stay near popular Chester attractions

Bonnie's Bundles Dolls

7.6/10 (4 reviews)
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.
See properties

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

How much are vacation packages to Chester?
You can score an awesome flight and hotel bundle for as little as CA $1,157. With one of our Travelocity vacation packages, a getaway to Chester has never looked more irresistible! Save both time and money and then get a start on packing those bags.
How long should my Chester vacation be?
Most visitors vacation in Chester for roughly 2 nights. That said, traveling is all about checking out new things and making cherished memories — why not stay a few more nights to do just that?
Where can I get the best vacation package deals for Chester?
There are exciting Chester package deals to be snapped up with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties around the globe? Remember this when you're ready to cross another place off your list.
Why should I book my Chester vacation package with Travelocity?
Whether you're searching for the ultimate unplugged escape or you crave the fun and excitement that only a big city can provide, booking everything with Travelocity saves you time, hassle and money. No need to search through hundreds of websites for the best deal — our Price Match Guarantee ensures you'll always get the lowest price, and our team of customer service experts are available 24/7.
Can I save on my Chester car rental if I bundle it with hotels and flights?
You certainly can — bundle your car, hotel and flight into a Chester vacation package and you'll save a handsome sum. With so much to uncover in Chester, having your own set of wheels will more than come in handy. Once you've buckled up, hit the wide open road and head to Fenway Park, a must-see attraction about 161 kilometers from Chester.
Which airport is best for Chester?
One top option is Lebanon Municipal Airport (LEB). From here, you'll have to travel southwest for roughly 48 kilometers to reach inner Chester. Another choice is Rutland Southern Vermont Regional Airport (RUT), which is 40 kilometers away from central Chester.
What is there to do in Chester?
DaVallia Art & Accents deserves a spot on your itinerary. Once you've crossed off this popular attraction, simply roam through the streets of Chester and experience what makes this cool destination tick.
Where should I stay when visiting Chester?
The Motel in the Meadow is the top choice of many travelers. Book soon before it's too late.

Photos of local treasures

Browse Chester vacation photos for more inspiration

A covered wooden bridge over a river, surrounded by rocky terrain and greenery.
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

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