
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.



Deerfield Valley Inn
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.

Top Chester hotels deals

Fullerton Inn
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
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
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
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
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
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
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.
Frequently asked questions
Photos of local treasures
Browse Chester vacation photos for more inspiration