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.
Mountaineer Inn

Mountaineer Inn

2 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
A seasonal outdoor pool is featured at this motel, along with free self parking. WiFi in public areas is free. A terrace, a garden, and express check-in are also on offer.
The Shire Woodstock

The Shire Woodstock

3 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) 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.
Deerfield Valley Inn

Deerfield Valley Inn

3 out of 5
Save 100% on your flight
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
This bed & breakfast features free WiFi in public areas, barbecue grills, and free self parking. A free bus station shuttle is offered as well. A garden, a lobby fireplace, and express check-in are also on offer.
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free buffet breakfast each morning. A garden is also provided.
Windham Hill Inn

Windham Hill Inn

4 out of 5
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. WiFi in public areas is free. A garden is also provided.

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
$159 nightly
The price is $173 total per night
$173 total
Jul 15 - Jul 16
Total includes 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
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Get rates
Stay at this cabin in Chester. Enjoy free WiFi, an in-room coffeemaker, and in-room fireplaces. Popular attractions Okemo Mountain Resort and Phineas Gage Memorial are located nearby.
Kitchen
Pet friendly
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$499 nightly
The price is $549 total per night
$549 total
Aug 10 - Aug 11
Total includes 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
Colonial Motel And Spa

Colonial Motel And Spa

3 out of 5
889 Putney Rd, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $120 total per night
$120 total
Jul 14 - Jul 15
Total includes taxes and fees
This smoke-free motel features a full-service spa, 2 indoor pools, and a restaurant. Business travelers can take advantage of the free WiFi in public areas. Enjoy the gym and perks like free self parking.
Pool
Hot Tub
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Free Cancellation
$210 nightly
The price is $231 total per night
$231 total
Jul 15 - Jul 16
Total includes 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.
Pool
Pet friendly
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
$215 nightly
The price is $236 total per night
$236 total
Jul 22 - Jul 23
Total includes 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.

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 $472. 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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