Deals on vacations and trips to Chester

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Chester flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $599, price is now $599 per person
$599
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Save 100% on your flight
Price was $1,825, price is now $1,438 per person
$1,438
per person
Mar 2 - Mar 9
found 14 hours ago
Roundtrip non-stop flight included
Milwaukee (MKE) to Springfield (VSF)
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.
Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Price was $1,220, price is now $1,022 per person
$1,022
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
The Vesper

The Vesper

3 out of 5
Price was $696, price is now $615 per person
$615
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) 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.
Lincoln Inn & Gallery

Lincoln Inn & Gallery

2 out of 5
West Woodstock
Price was $771, price is now $683 per person
$683
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Springfield (VSF)
This inn doesn't skimp on freebies - guests receive free WiFi and free self parking. A fireplace in the lobby and a picnic area are also provided.

Top Chester hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$379 nightly
The price is $417 total per night
$417 total
Dec 15 - Dec 16
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.
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $175 total per night
$175 total
Dec 17 - Dec 18
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. A garden and a picnic area are also provided.
Pet friendly
Parking included
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
$223 nightly
The price is $245 total per night
$245 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
This luxury hotel features a golf course, a full-service spa, and 4 restaurants. Enjoy the 3 outdoor tennis courts and get free self parking. Make the most of the indoor pool and 24-hour gym, and relax with drinks at one of the 2 bars/lounges.
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Free Cancellation
$204 nightly
The price is $225 total per night
$225 total
Dec 14 - Dec 15
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including food and water bowls. There's a seasonal outdoor pool on site, and a 24-hour front desk and a terrace are also provided.
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$144 nightly
The price is $157 total per night
$157 total
Dec 18 - Dec 19
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.
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
$134 nightly
The price is $147 total per night
$147 total
Jan 4 - Jan 5, 2026
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.
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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

Frequently asked questions

How much are vacation packages to Chester?
You can score an awesome flight and hotel bundle for as little as $599. 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

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