Book Exclusive Chester Vacation Packages

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Chester flight + hotel packages

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

Hampton Inn Brattleboro

2.5 out of 5
Price was CA $874, price is now CA $859 per person
CA $859
per person
Oct 31 - Nov 3
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. 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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was CA $1,125, price is now CA $927 per person
CA $927
per person
Oct 31 - Nov 3
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Springfield (VSF)
Stay at this 3-star 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.
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
Price was CA $1,115, price is now CA $1,103 per person
CA $1,103
per person
Oct 31 - Nov 3
found 4 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Brattleboro Bowl and United States Navy Seabee Bridge are located nearby.
Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Price was CA $1,200, price is now CA $1,141 per person
CA $1,141
per person
Oct 25 - Oct 27
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Springfield (VSF)
Stay at this 3-star B&B in West Dover. Enjoy free WiFi, free parking, and breakfast (surcharge). 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 $1,256, price is now CA $1,207 per person
CA $1,207
per person
Oct 25 - Oct 27
found 1 day ago
Roundtrip flight included
Edmonton (YEG) 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.

Top Chester hotels deals

The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Get rates
Stay at this 3-star 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.
Pet-friendly
Parking included
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is CA $825 per night
CA $825
CA $968 total
Sep 21 - Sep 22
includes taxes & fees
Stay at this 4.5-star 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 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 $192 per night
CA $192
CA $286 total
Sep 17 - Sep 18
includes taxes & fees
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Pool
Hot tub
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
The price is CA $187 per night
CA $187
CA $205 total
Sep 29 - Sep 30
includes taxes & fees
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. 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.
Pool
Hot tub
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd, Keene, NH
Free cancellation
Reserve now, pay when you stay
The price is CA $160 per night
CA $160
CA $174 total
Sep 23 - Sep 24
includes taxes & fees
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ashuelot River and Cheshire Children's Museum are located nearby.
Pool
Breakfast included
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
The price is CA $206 per night
CA $206
CA $227 total
Sep 21 - Sep 22
includes taxes & fees
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

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

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

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 $859. 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