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
Price was $729, price is now $529 per person
$529
per person
Dec 3 - Dec 8
found 7 hours 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 Covered Bridge Inn

The Covered Bridge Inn

2.5 out of 5
Price was $752, price is now $573 per person
$573
per person
Dec 3 - Dec 8
found 7 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
This hotel features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $681, price is now $563 per person
$563
per person
Oct 27 - Oct 30
found 6 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
A restaurant and a bar/lounge are featured at this hotel. Guests will appreciate free perks like free self parking and WiFi in public areas. Free parking and luggage storage are also offered on site.
Sinclair Inn Bed and Breakfast

Sinclair Inn Bed and Breakfast

4 out of 5
Price was $753, price is now $633 per person
$633
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Asheville (AVL) 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.
Holiday Inn Express Hotel & Suites Brattleboro by IHG

Holiday Inn Express Hotel & Suites Brattleboro by IHG

2.5 out of 5
Price was $844, price is now $739 per person
$739
per person
Dec 3 - Dec 8
found 7 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Springfield (VSF)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.

Top Chester hotels deals

The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
$245 nightly
The price is $270 total per night
$270 total
Oct 26 - Oct 27
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
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
$579 nightly
The price is $637 total per night
$637 total
Oct 26 - Oct 27
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
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
$186 nightly
The price is $204 total per night
$204 total
Oct 26 - Oct 27
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
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
Free Cancellation
Reserve now, pay when you stay
$193 nightly
The price is $213 total per night
$213 total
Oct 26 - Oct 27
Total with taxes and fees
This smoke-free hotel features ski-in/ski-out access, a full-service spa, and 2 restaurants. 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.
Pool
Hot Tub
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road, Keene, NH
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $101 total per night
$101 total
Sep 29 - Sep 30
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. There's a gym on site, and a snack bar/deli and a picnic area are also provided.
Breakfast included
Pet friendly
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
$125 nightly
The price is $136 total per night
$136 total
Oct 5 - Oct 6
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
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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 $529. 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