Book Exclusive Chester Vacation Packages

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Chester flight + hotel packages

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

Windham Hill Inn

4 out of 5
Price was CA $1,743, price is now CA $1,528 per person
CA $1,528
per person
Jan 18 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Stay at this B&B in West Townshend. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Hot Glass Works and Ball Mountain State Park are located nearby.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Price was CA $3,124, price is now CA $2,431 per person
CA $2,431
per person
Jan 18 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Book a stay at this 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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was CA $3,056, price is now CA $2,384 per person
CA $2,384
per person
Jan 18 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Book a stay at this spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Okemo Mountain Resort and Jackson Gore Parking are located nearby.
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Clock Tower Base Area
Price was CA $5,438, price is now CA $4,587 per person
CA $4,587
per person
Jan 18 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
Stay at this vacation home in Ludlow. Enjoy free parking, daily housekeeping, and laundry facilities. Popular attractions Okemo Mountain Resort and Skywalker Carpet are located nearby.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
Price was CA $2,352, price is now CA $1,990 per person
CA $1,990
per person
Jan 18 - Jan 24
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Springfield (VSF)
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.

Top Chester hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is CA $521 per night
CA $521
CA $634 total
Jan 6 - Jan 7, 2026
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.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
The price is CA $198 per night
CA $198
CA $226 total
Dec 18 - Dec 19
includes taxes & fees
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Free cancellation
Reserve now, pay when you stay
Get rates
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Billings Park and Trail and Red Wagon Toy Company are located nearby.
Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
89 Grand Summit Way West Dover VT
The price is CA $317 per night
CA $317
CA $380 total
Dec 18 - Dec 19
includes taxes & fees
Book a stay at this 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.
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
Free cancellation
Reserve now, pay when you stay
The price is CA $282 per night
CA $282
CA $389 total
Dec 18 - Dec 19
includes taxes & fees
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
The price is CA $221 per night
CA $221
CA $297 total
Jan 5 - Jan 6, 2026
includes taxes & fees
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
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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 $1,528. 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