Deals on vacations and trips to Chester
Save when you book Chester package deals
Chester flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Mount Snow Grand Summit Resort
per person
Jun 9 - Jun 13
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
This smoke-free resort features ski-in/ski-out access, a full-service spa, and a restaurant. Enjoy the outdoor pool and perks like free valet parking and a free area shuttle. You'll appreciate the gym, bar/lounge, and laundry facilities.
Jackson Gore Village
Jackson Gore Base Area
per person
Jun 9 - Jun 13
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
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.
Top Chester hotels deals
Fullerton Inn
40 The Common, Chester, VT
Free Cancellation
Reserve now, pay when you stay
The price is $141 per night
$141
includes taxes & fees
$129 per night
May 6 - May 7
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
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
The price is $373 per night
$373
includes taxes & fees
$339 per night
May 26 - May 27
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
3567 Main Street Route 7A, Manchester, VT
Free Cancellation
Reserve now, pay when you stay
The price is $173 per night
$173
includes taxes & fees
$157 per night
May 7 - May 8
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
Best Western Plus Keene Hotel
401 Winchester St, Keene, NH
Free Cancellation
Reserve now, pay when you stay
The price is $141 per night
$141
includes taxes & fees
$130 per night
May 11 - May 12
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the 24-hour gym and free perks like buffet breakfast and free self parking.
Pool
Breakfast included
Colonial Motel And Spa
889 Putney Rd, Brattleboro, VT
Free Cancellation
Reserve now, pay when you stay
The price is $120 per night
$120
includes taxes & fees
$109 per night
May 5 - May 6
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
The Shire Woodstock
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
The price is $132 per night
$132
includes taxes & fees
$120 per night
May 7 - May 8
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
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.
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.
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