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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*
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10 (31 reviews)
Luxury 3BR Cabin 5 min Drive to Okemo and on Ski Shuttle Route
Holiday home · 2 Guests · 1 Bedroom
$613 /night*
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10 (5 reviews)
17-Acre Vermont Escape w/ Panoramic Mountain Views
Holiday home · 2 Guests · 1 Bedroom
$664 /night*
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9.6 (19 reviews)
| Handmade 4 Bed Log Cabin | 5 Min From Skiing |
Holiday home · 2 Guests · 1 Bedroom
$200 /night*
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8.0 (71 reviews)
Fullerton Inn & Restaurant
Inn · 2 Guests · 1 Bedroom
$146 /night
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A Beautiful Art Studio & Loft!
Holiday home · 2 Guests · 1 Bedroom
$295 /night*
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10 (3 reviews)
Cozy Chalet on Magic Mountain
Chalet · 2 Guests · 1 Bedroom
$461 /night*
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10 (41 reviews)
Charming Ski Chalet Minutes From Okemo Mountain!
Chalet · 2 Guests · 1 Bedroom
$900 /night*
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9.6 (10 reviews)
The Hideaway Chalet. 3bed + sleeping loft on 10 acres. Dog friendly
Holiday home · 2 Guests · 1 Bedroom
$467 /night*
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8.0 (1 review)
Wild Blossom Farmhouse- a lovely Vermont Getaway
Holiday home · 2 Guests · 1 Bedroom
$333 /night*
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10 (75 reviews)
Panoramic Mountain View, Lots To Do, Or Enjoy Doing Nothing
Holiday home · 2 Guests · 1 Bedroom
$300 /night*
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9.6 (30 reviews)
Comfortable home with jetted tub, patio, & W/D- near skiing
Holiday home · 2 Guests · 1 Bedroom
$539 /night*
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Londonderry Retreat ~ 3 Mi to Lowell Lake!
Cottage · 2 Guests · 1 Bedroom
$534 /night
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9.4 (11 reviews)
King & Queen Suite in Historic Inn Circa 1780
B & B · 2 Guests · 1 Bedroom
$209 /night*
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9.0 (110 reviews)
The Pointe at Castle Hill Resort & Spa
Resort · 2 Guests · 1 Bedroom
$282 /night
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9.2 (9 reviews)
Affordable family-friendly holiday home
Holiday home · 2 Guests · 1 Bedroom
$625 /night*
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8.6 (16 reviews)
Stone Hearth Inn and Eatery
B & B · 2 Guests · 1 Bedroom
$202 /night
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10 (8 reviews)
The Pioneer House
Holiday home · 2 Guests · 1 Bedroom
$250 /night*
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9.2 (195 reviews)
Rowell's Inn
B & B · 2 Guests · 1 Bedroom
$333 /night
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5.2 (32 reviews)
Rodeway Inn
Hotel · 2 Guests · 1 Bedroom
$99 /night
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Airbnb, Vacation House with Fireplace in Chester, VT

10 (5 reviews)
17-Acre Vermont Escape w/ Panoramic Mountain Views
Holiday home · 2 Guests · 1 Bedroom
$664 /night*
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9.6 (10 reviews)
The Hideaway Chalet. 3bed + sleeping loft on 10 acres. Dog friendly
Holiday home · 2 Guests · 1 Bedroom
$467 /night*
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8.8 (8 reviews)
Room in Historic Inn! 20 Minutes to Okemo!
B & B · 2 Guests · 1 Bedroom
$229 /night*
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What Are The Most Popular Amenities in Chester, VT?
Top Rental Amenities in Chester, VT
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Check above for the most common and the least popular rental amenities in Chester, and pick the one that fits your preference easily. In Chester, 1026 rentals offer Internet or Wifi, 991 rentals offer TV, 951 rentals offer Bed linens provided. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Pool, Hot Tub.
Which Price Range Is Most Typical in Chester, VT Area?
Vacation House & Condo Rental Price Information in Chester, VT
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The graph shows the percentages of vacation homes in each price bucket. Chester has the largest percentage (16.45%) of homes in $500+ price range.
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Which Accommodations Should I Pick in Chester, VT?
Rental Accommodation Info in Chester, VT
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In Chester, 52.93% of listings are House, which is the most popular accommodation out of 18 total accommodation types. Avg price per night for House is around $362. And the most searched amenities for House accommodation is Pool.The least popular accommodation in Chester is Bed And Breakfast rentals
How Many Accommodations Are Pets Allowed in Chester, VT?
Pets Allowed vs Not Allowed in Chester, VT
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27.95% of vacation homes in Chester are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Trail Recommendations in Chester, VT Area?
Best Trails In Chester, VT
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If you like outdoor activities, we highly recommend you to visit those famous trails: Hawks Mountain Trail, The Lost Mine, The Lost Mine Trail, Mount Ephraim, Big Bear Loop, Williams River, Lake Summit via Ledge Road, Hoyt's Landing, The Toonerville Trail, Lowell Lake.
Any RV Campgrounds in Chester, VT?
Campgrounds Recommendations In Chester, VT
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The best RV campgrounds here in Chester are: Brattleboro North KOA, Grout Pond Campground, Winhall Brook Campground, Otter Creek Campground, Kenolie Village Campground, Bald Mountain Campground, Surry Mountain Lake Campground, Hapgood Pond Recreation Area, Getaway Mountain Campground, Tree Farm Campground.
How Many Airports in Chester, VT?
Suggested Airports in Chester, VT
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Here are the airports that located near Chester:

Other Vacation Rentals Ideas

Airbnb, Vacation House with Full Kitchen, and Other Rental Options in Chester, VT

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*
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10 (28 reviews)
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays
Holiday home · 2 Guests · 1 Bedroom
$1,500 /night*
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9.6 (22 reviews)
Beautiful and Brand New Ski House
Holiday home · 2 Guests · 1 Bedroom
$450 /night*
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Airbnb, Vacation Condo with Pool, and Other Rental Options in Chester, VT

9.6 (25 reviews)
Retro Modern Barn Apartment in the Heart of Grafton
Apartment · 2 Guests · 1 Bedroom
$185 /night*
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10 (17 reviews)
Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside
Condo · 2 Guests · 1 Bedroom
$1,850 /night*
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9.6 (150 reviews)
Okemo Mt. Family Affordable 1st floor, village shuttle, walk to town, Dogs OK
Apartment · 2 Guests · 1 Bedroom
$450 /night*
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* 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.
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