Airbnb, Vacation Rentals in Chester, VT
Compare 2,218 available vacation home properties, starts from $24
Navigate forward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Navigate backward to interact with the calendar and select a date. Press the question mark key to get the keyboard shortcuts for changing dates.
Find the best vacation rental
Save Up To 76%
Airbnb, Vacation rentals and hotel deals in Chester, VT
9.4 (3 reviews)
4BR Green Mountain Magic in Heart of Vermont with AC & fans
Chalet · 2 Guests · 1 Bedroom
$603 /night*
10 (31 reviews)
Luxury 3BR Cabin 5 min Drive to Okemo and on Ski Shuttle Route
Holiday home · 2 Guests · 1 Bedroom
$613 /night*
10 (5 reviews)
17-Acre Vermont Escape w/ Panoramic Mountain Views
Holiday home · 2 Guests · 1 Bedroom
$664 /night*
9.6 (19 reviews)
| Handmade 4 Bed Log Cabin | 5 Min From Skiing |
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
8.0 (71 reviews)
Fullerton Inn & Restaurant
Inn · 2 Guests · 1 Bedroom
$146 /night
A Beautiful Art Studio & Loft!
Holiday home · 2 Guests · 1 Bedroom
$295 /night*
10 (3 reviews)
Cozy Chalet on Magic Mountain
Chalet · 2 Guests · 1 Bedroom
$461 /night*
10 (41 reviews)
Charming Ski Chalet Minutes From Okemo Mountain!
Chalet · 2 Guests · 1 Bedroom
$900 /night*
9.6 (10 reviews)
The Hideaway Chalet. 3bed + sleeping loft on 10 acres. Dog friendly
Holiday home · 2 Guests · 1 Bedroom
$467 /night*
8.0 (1 review)
Wild Blossom Farmhouse- a lovely Vermont Getaway
Holiday home · 2 Guests · 1 Bedroom
$333 /night*
10 (75 reviews)
Panoramic Mountain View, Lots To Do, Or Enjoy Doing Nothing
Holiday home · 2 Guests · 1 Bedroom
$300 /night*
9.6 (30 reviews)
Comfortable home with jetted tub, patio, & W/D- near skiing
Holiday home · 2 Guests · 1 Bedroom
$539 /night*
Londonderry Retreat ~ 3 Mi to Lowell Lake!
Cottage · 2 Guests · 1 Bedroom
$534 /night
9.4 (11 reviews)
King & Queen Suite in Historic Inn Circa 1780
B & B · 2 Guests · 1 Bedroom
$209 /night*
9.0 (110 reviews)
The Pointe at Castle Hill Resort & Spa
Resort · 2 Guests · 1 Bedroom
$282 /night
9.2 (9 reviews)
Affordable family-friendly holiday home
Holiday home · 2 Guests · 1 Bedroom
$625 /night*
8.6 (16 reviews)
Stone Hearth Inn and Eatery
B & B · 2 Guests · 1 Bedroom
$202 /night
10 (8 reviews)
The Pioneer House
Holiday home · 2 Guests · 1 Bedroom
$250 /night*
9.2 (195 reviews)
Rowell's Inn
B & B · 2 Guests · 1 Bedroom
$333 /night
5.2 (32 reviews)
Rodeway Inn
Hotel · 2 Guests · 1 Bedroom
$99 /night
Airbnb, Vacation House with Fireplace in Chester, VT
Fireplace
10 (5 reviews)
17-Acre Vermont Escape w/ Panoramic Mountain Views
Holiday home · 2 Guests · 1 Bedroom
$664 /night*
Fireplace
9.6 (10 reviews)
The Hideaway Chalet. 3bed + sleeping loft on 10 acres. Dog friendly
Holiday home · 2 Guests · 1 Bedroom
$467 /night*
Fireplace
8.8 (8 reviews)
Room in Historic Inn! 20 Minutes to Okemo!
B & B · 2 Guests · 1 Bedroom
$229 /night*
What Are The Most Popular Amenities in Chester, VT?
Top Rental Amenities in Chester, VT
+
Which Price Range Is Most Typical in Chester, VT Area?
Vacation House & Condo Rental Price Information in Chester, VT
+
Which Accommodations Should I Pick in Chester, VT?
Rental Accommodation Info in Chester, VT
+
How Many Accommodations Are Pets Allowed in Chester, VT?
Pets Allowed vs Not Allowed in Chester, VT
+
What Are The Must-Visit Places in Chester, VT?
Must Visit Places In Chester, VT
+
Trail Recommendations in Chester, VT Area?
Best Trails In Chester, VT
+
Any RV Campgrounds in Chester, VT?
Campgrounds Recommendations In Chester, VT
+
How Many Airports in Chester, VT?
Suggested Airports in Chester, VT
+
Other Vacation Rentals Ideas
Airbnb, Vacation House with Full Kitchen, and Other Rental Options in Chester, VT
Full Kitchen
9.2 (19 reviews)
DISCOUNTED RATES AVAILABLE! 10% to 15% off for 3 or more days booked.
Holiday home · 2 Guests · 1 Bedroom
$950 /night*
Full Kitchen
10 (28 reviews)
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Holiday home · 2 Guests · 1 Bedroom
$1,500 /night*
Full Kitchen
9.6 (22 reviews)
Beautiful and Brand New Ski House
Holiday home · 2 Guests · 1 Bedroom
$450 /night*
Airbnb, Vacation Condo with Pool, and Other Rental Options in Chester, VT
Pool
9.6 (25 reviews)
Retro Modern Barn Apartment in the Heart of Grafton
Apartment · 2 Guests · 1 Bedroom
$185 /night*
Pool
10 (17 reviews)
Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside
Condo · 2 Guests · 1 Bedroom
$1,850 /night*
Pool
9.6 (150 reviews)
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Apartment · 2 Guests · 1 Bedroom
$450 /night*
* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.