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Chester vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Chester

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Superhost
Guesthouse in Springfield
Connecticut River-Cozy Cottage
This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.
$101 per night
Superhost
Barn in Chester
Inviting studio apartment above barn in Vermont
This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.
$96 per night
Superhost
Guest suite in Chester
Chester Carriage House-Cozy-Quintessential Vermont
Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and pubs, antique shops, art galleries, yoga studio and a country market. Explore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers + breweries. Close proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington) Come experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!
$143 per night

Stay near Chester's top sights

Country Girl Diner29 locals recommend
MacLaomainn's Scottish Pub31 locals recommend
The Pizza Stone VT.27 locals recommend
Fullerton Inn12 locals recommend
Southern Pie Cafe18 locals recommend
the Free Range15 locals recommend

Other great vacation rentals in Chester

Superhost
Guesthouse in Putney
Cozy cottage loft and retreat
$115 per night
Superhost
Apartment in Chester
Lovely 2 Bedroom Apartment w/deck & pond view
$157 per night
Superhost
Home in Town of Rockingham
Beautiful Home in the Mountains - The Fox & Owl
$220 per night
Superhost
Home in Grafton
Retro Modern Barn Apartment
$175 per night
Superhost
Apartment in Town of Rockingham
Stunning Studio in historic Downtown Bellows Falls
$89 per night
Superhost
Cottage in Town of Rockingham
Peaceful Mountain Cottage
$102 per night
Superhost
Apartment in Weathersfield
The Loft at Weathersfield
$140 per night
Superhost
Cabin in Weston
Idyllic Vermont Cabin-Clean, Fast WiFi, Generator!
$220 per night
Superhost
Home in Chester
Private Home in Chester, VT
$295 per night
Superhost
Home in Chester
Serenity Awaits Peaceful Getaway on 6 acres + view
$290 per night
Superhost
Cabin in Chester
Handmade 3 Bedroom Log Cabin | 5 Min From Skiing
$204 per night
Superhost
Tiny home in Chester
Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo
$251 per night

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Chester