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.
Jackson Gore Village
Jackson Gore Base Area
Price was $827, price is now $648 per person
$648
per person
Oct 9 - Oct 15
found 13 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Solitude Village at Okemo
Clock Tower Base Area
Save 100% on your flight
Price was $1,316, price is now $1,003 per person
$1,003
per person
Oct 9 - Oct 15
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free aparthotel. Enjoy the indoor pool and perks like free self parking and free WiFi. A gym, a hot tub, and a sauna are also on offer.
Chalet 239
Save 100% on your flight
Price was $906, price is now $693 per person
$693
per person
Oct 9 - Oct 15
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
The motel doesn't skimp on freebies - guests receive free on-the-go breakfast and free self parking. A picnic area and a virtual front desk are also provided.
Winterplace at Okemo
Clock Tower Base Area
Save 100% on your flight
Price was $977, price is now $758 per person
$758
per person
Oct 9 - Oct 15
found 13 hours ago
Roundtrip flight included
Orlando (MCO) to Springfield (VSF)
Ski-in/ski-out access and an indoor pool are featured at this smoke-free aparthotel. Enjoy the hot tub and perks like free self parking and free WiFi. Express check-out, laundry facilities, and barbecue grills are also on offer.
Mount Snow Grand Summit Resort
Save 100% on your flight
Price was $884, price is now $689 per person
$689
per person
Oct 9 - Oct 15
found 13 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Top Chester hotels deals
Fullerton Inn
40 The Common, Chester, VT
Free Cancellation
Reserve now, pay when you stay
$139 nightly
The price is $152 total per night
$152 total
Sep 1 - Sep 2
Total with 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
Woodstock Inn & Resort
Fourteen The Green, Woodstock, VT
$449 nightly
The price is $494 total per night
$494 total
Sep 1 - Sep 2
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 Shire Woodstock
46 Pleasant St., Woodstock, VT
Free Cancellation
Reserve now, pay when you stay
$212 nightly
The price is $233 total per night
$233 total
Aug 26 - Aug 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
The Equinox Golf Resort & Spa
3567 Main Street Route 7A, Manchester, VT
Free Cancellation
Reserve now, pay when you stay
$185 nightly
The price is $203 total per night
$203 total
Sep 3 - Sep 4
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
Days Inn by Wyndham Keene NH
3 Ash Brook Road, Keene, NH
Free Cancellation
Reserve now, pay when you stay
$111 nightly
The price is $121 total per night
$121 total
Sep 1 - Sep 2
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, Ascend Hotel Collection
175 Key Rd, Keene, NH
Free Cancellation
Reserve now, pay when you stay
$125 nightly
The price is $136 total per night
$136 total
Aug 31 - Sep 1
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
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.