Book Exclusive Chester Vacation Packages

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Chester flight + hotel packages

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

Mountaineer Inn

2 out of 5
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.
Chalet 239

Chalet 239

2 out of 5
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 breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Mount Snow Golf Course are located nearby.
Mount Snow Lodging

Mount Snow Lodging

3 out of 5
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

Mount Snow Grand Summit Resort

3 out of 5
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.
Inn At Mount Snow

Inn At Mount Snow

2 out of 5
per person
May 4 - May 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Springfield (VSF)
Book a stay at this ski hotel in West Dover. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Mount Snow and Snow Lake 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 $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

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

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 $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

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
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

Colonial Motel And Spa

3 out of 5
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

Hampton Inn and Suites Manchester

2.5 out of 5
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
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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.

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.

Bonnie's Bundles Dolls

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.

DaVallia Art & Accents

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 $958. 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