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Chester flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was CA $1,596, price is now CA $1,570 per person
CA $1,570
per person
Dec 26 - Dec 28
found 5 hours ago
Roundtrip flight included
Halifax (YHZ) 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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was CA $1,750, price is now CA $1,695 per person
CA $1,695
per person
Dec 26 - Dec 28
found 5 hours ago
Roundtrip flight included
Halifax (YHZ) 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.
The Hermitage Inn Vermont

The Hermitage Inn Vermont

4 out of 5
Price was CA $2,145, price is now CA $2,087 per person
CA $2,087
per person
Dec 26 - Dec 28
found 5 hours ago
Roundtrip flight included
Halifax (YHZ) to Springfield (VSF)
Book a stay at this golf inn in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Back Draft are located nearby.
Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91

2.5 out of 5
Price was CA $1,697, price is now CA $1,680 per person
CA $1,680
per person
Dec 26 - Dec 28
found 5 hours ago
Roundtrip flight included
Halifax (YHZ) 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 helpful staff in our reviews. Popular attractions United States Navy Seabee Bridge and Brattleboro Bowl are located nearby.
Black Mountain Inn

Black Mountain Inn

2 out of 5
Price was CA $1,660, price is now CA $1,649 per person
CA $1,649
per person
Dec 26 - Dec 28
found 5 hours ago
Roundtrip flight included
Halifax (YHZ) to Springfield (VSF)
Stay at this hotel 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 United States Navy Seabee Bridge are located nearby.

Top Chester hotels deals

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
The price is CA $183 per night
CA $183
CA $199 total
Dec 3 - Dec 4
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 $255 per night
CA $255
CA $278 total
Nov 17 - Nov 18
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.
Kitchen
Pet-friendly
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $467 per night
CA $467
CA $576 total
Nov 30 - Dec 1
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 Quechee Gorge Bridge and Middle Covered Bridge are located nearby.
Pool
Hot tub
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
The price is CA $226 per night
CA $226
CA $270 total
Nov 16 - Nov 17
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
Colonial Motel

Colonial Motel

3 out of 5
889 Putney Rd Brattleboro VT
Free cancellation
Reserve now, pay when you stay
The price is CA $121 per night
CA $121
CA $133 total
Nov 15 - Nov 16
includes taxes & fees
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.
Breakfast included
Pet-friendly
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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 $1,570. 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 nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.
A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

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