Deals on vacations and trips to Chester

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Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $846, price is now $756 per person
$756
per person
May 22 - May 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Ski-in/ski-out access, 2 restaurants, and 3 hot tubs are all featured at this smoke-free hotel. There's a free ski shuttle, and ski lessons, ski passes and ski storage are available on site. Bring the family and enjoy the mini golf, playground, and arcade/game room.
Treehouse Home in Ludlow

Treehouse Home in Ludlow

2 out of 5
Price was $2,632, price is now $2,203 per person
$2,203
per person
May 22 - May 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. Laundry facilities and barbecue grills are also provided.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $988, price is now $833 per person
$833
per person
May 22 - May 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Winterplace at Okemo, A Vail Resorts Property

Winterplace at Okemo, A Vail Resorts Property

4 out of 5
Clock Tower Base Area
Price was $898, price is now $809 per person
$809
per person
May 22 - May 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the hot tub and conveniences like express check-out and laundry facilities.
The Vesper

The Vesper

3 out of 5
Price was $1,021, price is now $924 per person
$924
per person
May 22 - May 25
found 2 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Springfield (VSF)
This bed & breakfast doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A virtual front desk are provided for your convenience.

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
$129 nightly
The price is $141 total per night
$141 total
Mar 17 - Mar 18
Total with taxes and fees
A restaurant and a bar/lounge are featured at this inn. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A business center, a garden, and luggage storage are also on offer.
Breakfast included
Parking included
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$135 nightly
The price is $146 total per night
$146 total
Mar 25 - Mar 26
Total with taxes and fees
A full-service spa, an indoor pool, and a restaurant are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$349 nightly
The price is $384 total per night
$384 total
Mar 22 - Mar 23
Total with taxes and fees
This luxury resort features a golf course, a full-service spa, and 4 restaurants. Enjoy the 2 indoor tennis courts and perks like free valet parking and free WiFi. Relax with a drink at one of the 2 bars/lounges and enjoy the 2 hot tubs and indoor pool.
Pool
Hot Tub
Hideaway Inn Mt. Snow

Hideaway Inn Mt. Snow

2 out of 5
270 Handle Rd West Dover VT
Free Cancellation
Reserve now, pay when you stay
$135 nightly
The price is $149 total per night
$149 total
Mar 23 - Mar 24
Total with taxes and fees
This hotel features a seasonal outdoor pool and a sauna. Enjoy the free ski shuttle and onsite ski storage. Guests will appreciate free perks like free self parking and WiFi in public areas.
Pool
Pet friendly
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
$139 nightly
The price is $153 total per night
$153 total
Mar 29 - Mar 30
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the hot tub and free perks like buffet breakfast and free self parking.
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
5383 Main St Manchester Center VT
Free Cancellation
$113 nightly
The price is $124 total per night
$124 total
Mar 29 - Mar 30
Total with taxes and fees
This smoke-free hotel features a golf course, 2 outdoor tennis courts, and a restaurant. Enjoy the indoor pool and free perks like continental breakfast and free self parking. You'll appreciate the seasonal outdoor pool, bar/lounge, and free newspapers.
Pool
Hot Tub
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See all available properties in Chester
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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

Frequently asked questions

How much are vacation packages to Chester?
You can score an awesome flight and hotel bundle for as little as $756. 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 100 mi 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 30 mi to reach inner Chester. Another choice is Rutland Southern Vermont Regional Airport (RUT), which is 25 mi 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

aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

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