Chester Vacation Rentals

Icon
Icon
Rural Chester Farmhouse
Icon

3 Bedroom Farmhouse in Chester

3 Bedrooms
2 Bathrooms
$128 - $479 / night (excl. fees & taxes)
Icon
Icon
Valley Views with Hot Tub
Icon

Hilltop getaway near multiple ski mountains

4 Bedrooms
3½ Bathrooms
$342 - $1070 / night (excl. fees & taxes)
Icon
Icon
Green Leaf Inn
Icon

3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
1 review
$150 / night (excl. fees & taxes)
Icon
Icon
Hot Tub Chalet on Magic Mountain
Icon

Hot Tub and Enough Space for 14!

5 Bedrooms
2½ Bathrooms
$233 - $817 / night (excl. fees & taxes)
Icon
Icon
The Historic Rideout
Icon

Historic Rideout 16m to Okemo Walk to Town

6 Bedrooms
6 Bathrooms
$444 - $1442 / night (excl. fees & taxes)
Icon
Icon
Hillside Haven
Icon

Hillside Haven Victorian! Hot Tub Firepit 5m-Okemo

5 Bedrooms
3 Bathrooms
$298 - $1545 / night (excl. fees & taxes)
Icon
Icon
Londonderry Loft with Sauna
Icon

4 Bedroom and Steam Sauna in Londonderry

4 Bedrooms
2 Bathrooms
Icon
Icon
Red Brick Retreat
Icon

Red Brick Retreat - 8br 6ba Hot Tub Sauna Home Gym

8 Bedrooms
6 Bathrooms
$979 - $2060 / night (excl. fees & taxes)
Icon
Icon
Trailside Chalet
Icon

Walk to Okemo Ski Lift - Private Classic VT Ski Chalet w/ Fire Pit & Pool Table

5 Bedrooms
2 Bathrooms
4.9IconIconIconIconIcon
59 reviews
$250 - $2000 / night (excl. fees & taxes)
Icon
Icon
Clocktower Chalet
Icon

*January 50% Discount* Walk to Okemo Lodge & Lifts. Private Home with Hot Tub

4 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
31 reviews
$275 - $2000 / night (excl. fees & taxes)
Icon
Icon
River Views with pool table and more!
Icon

Luxurious Home w/ View of the CT River

5 Bedrooms
3 Bathrooms
Icon
Icon
Londonderry Links
Icon

3 Bedrooms
2 Bathrooms
4.88IconIconIconIconIcon
25 reviews
$200 - $1136 / night (excl. fees & taxes)
Icon
Icon
Icon
2 Bdrm, Lower Level, Okemo, 25 Acre Mtn Playground
Icon

25 Acre Mountain Playground, Close to Okemo, 2 Bedroom

2 Bedrooms
1 Bathroom
5IconIconIconIconIcon
27 reviews
$250 - $300 / night (excl. fees & taxes)
Icon
Icon
Icon
2 Bdrm, Upper Level, Okemo, 25 Acre Mtn Playground
Icon

Close to Okemo, 25 Acre Mountain Playground, 2 Bedroom

2 Bedrooms
1 Bathroom
5IconIconIconIconIcon
13 reviews
$250 - $300 / night (excl. fees & taxes)
Icon
Icon
The Tower House
Icon

6 Bedrooms
4 Bathrooms
4.89IconIconIconIconIcon
9 reviews
$419 - $1849 / night (excl. fees & taxes)
Icon
Icon
Mountain View Manor
Icon

Mountain View Manor - Expansive Views, Hot Tub, Hiking & Nearby Lakes!

6 Bedrooms
5 Bathrooms
$670 - $2122 / night (excl. fees & taxes)
Icon
Icon
Icon
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Icon

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

6 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
107 reviews
$550 / night (excl. fees & taxes)
Icon
Icon
Drop Point Cabin
Icon

4 Bedrooms
3 Bathrooms
4.72IconIconIconIconIcon
25 reviews
$300 - $1717 / night (excl. fees & taxes)
Icon
Icon
Stratton Loft with Pool
Icon

Stratton Loft with Pool

4 Bedrooms
2 Bathrooms
$170 - $715 / night (excl. fees & taxes)
Icon
Icon
The Mountain Escape
Icon

4 Bedrooms
3 Bathrooms
$337 - $1400 / night (excl. fees & taxes)
    1 – 20 Rentals