Chester Vacation Rentals
3 Bedroom Farmhouse in Chester
3 Bedrooms
2 Bathrooms
4 Guides
$102 - $479 / night (excl. fees & taxes)
Hilltop getaway near multiple ski mountains
4 Bedrooms
3½ Bathrooms
4 Guides
$249 - $1070 / night (excl. fees & taxes)
Hot Tub and Enough Space for 14!
5 Bedrooms
2½ Bathrooms
4 Guides
$233 - $817 / night (excl. fees & taxes)
Historic Rideout 16m to Okemo Walk to Town
6 Bedrooms
6 Bathrooms
4 Guides
$361 - $1442 / night (excl. fees & taxes)
Hillside Haven Victorian! Hot Tub Firepit 5m-Okemo
5 Bedrooms
3 Bathrooms
4 Guides
$307 - $1545 / night (excl. fees & taxes)
Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym
8 Bedrooms
6 Bathrooms
4 Guides
$515 - $2060 / night (excl. fees & taxes)
Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table
5 Bedrooms
2 Bathrooms
4 Guides
4.9
59 reviews$250 - $1600 / night (excl. fees & taxes)
Walk to Okemo Base Lodge & Lifts. Private On Mountain Home with Hot Tub/Fire Pit
4 Bedrooms
2 Bathrooms
4 Guides
5
31 reviews$275 - $1800 / night (excl. fees & taxes)
Luxurious Home w/ View of the CT River
5 Bedrooms
3 Bathrooms
4 Guides
3 Bedrooms
2 Bathrooms
4 Guides
4.88
25 reviews$200 - $1152 / night (excl. fees & taxes)
25 Acre Mountain Playground, Close to Okemo, 2 Bedroom
2 Bedrooms
1 Bathroom
4 Guides
5
27 reviews$175 - $300 / night (excl. fees & taxes)
Close to Okemo, 25 Acre Mountain Playground, 2 Bedroom
2 Bedrooms
1 Bathroom
4 Guides
5
13 reviews$200 - $300 / night (excl. fees & taxes)
Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!
6 Bedrooms
5 Bathrooms
4 Guides
$670 - $2122 / night (excl. fees & taxes)
4 Bedrooms
3 Bathrooms
4 Guides
4.72
25 reviews$300 - $1724 / night (excl. fees & taxes)
Stratton Loft with Pool
4 Bedrooms
2 Bathrooms
4 Guides
$170 - $715 / night (excl. fees & taxes)
Scandinavian Sauna near hiking and views
3 Bedrooms
3 Bathrooms
4 Guides
$194 - $672 / night (excl. fees & taxes)
Terms, Privacy, Currency & More
Save to Favorites
More filters
Beds & Baths
Bedrooms
0 +
Bathrooms
0 +More options
Pets
Managed by
Room Type
Property Type
Indoor Amenities
Outdoor Amenities
Languages