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.
Solitude Village at Okemo by Vail Resorts

Solitude Village at Okemo by Vail Resorts

4 out of 5
Clock Tower Base Area
Price was $806, price is now $741 per person
$741
per person
Sep 25 - Sep 28
found 18 hours ago
Roundtrip non-stop flight included
Asheville (AVL) to Springfield (VSF)
This smoke-free aparthotel's ski-in/ski-out access and 2 hot tubs are some of the highlights. Enjoy the gym and perks like free self parking and free WiFi. A sauna is also provided.
The Hartness House

The Hartness House

3 out of 5
Price was $887, price is now $797 per person
$797
per person
Sep 25 - Sep 28
found 18 hours ago
Roundtrip non-stop flight included
Asheville (AVL) to Springfield (VSF)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in and express check-out 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 $882, price is now $806 per person
$806
per person
Sep 25 - Sep 28
found 18 hours ago
Roundtrip non-stop flight included
Asheville (AVL) 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.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $1,042, price is now $969 per person
$969
per person
Nov 1 - Nov 5
found 22 hours ago
Roundtrip flight included
Detroit (DTW) to Springfield (VSF)
This bed & breakfast doesn't skimp on freebies - guests receive free full breakfast and free WiFi. A garden and a picnic area are also provided.
The Weston

The Weston

5 out of 5
Price was $1,408, price is now $1,310 per person
$1,310
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Springfield (VSF)
This luxury guesthouse features a full-service spa and a restaurant. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.

Top Chester hotels deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$449 nightly
The price is $494 total per night
$494 total
Sep 7 - Sep 8
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.
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
$120 nightly
The price is $130 total per night
$130 total
Sep 2 - Sep 3
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. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
$250 nightly
The price is $275 total per night
$275 total
Sep 9 - Sep 10
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.
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
$279 nightly
The price is $307 total per night
$307 total
Sep 1 - Sep 2
Total with taxes and fees
This hotel features an indoor pool, a hot tub, and a restaurant. Bring the family and enjoy the children's pool, playground, and arcade/game room. Enjoy the gym and perks like free self parking and free WiFi.
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
$154 nightly
The price is $168 total per night
$168 total
Aug 17 - Aug 18
Total with taxes and fees
This resort features a restaurant, an outdoor tennis court, and a bar/lounge. A business center, a lobby fireplace, and a picnic area are also on offer.
Restaurant
Air conditioning
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
$198 nightly
The price is $217 total per night
$217 total
Aug 24 - Aug 25
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.
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.

Stay near popular Chester attractions

DaVallia Art & Accents

10.0/10 (2 reviews)
Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.
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Frequently asked questions

How much are vacation packages to Chester?
You can score an awesome flight and hotel bundle for as little as $741. 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

A covered wooden bridge over a river, surrounded by rocky terrain and greenery.
A nighttime view of a large, illuminated bridge with intricate metalwork and a prominent arch.

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