We found 961 vacation rentals — enter your dates for availability
Discover a selection of 1,000 vacation rentals in Chester, VT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including WiFi and fireplaces. Prices start at $100 per night, and houses and cabins are popular options for a stay in Chester. Either way, you'll find a rental for everyone's needs.
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Find the best place to stay — Chester
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Things to do
Turn back time in Chester’s Stone Village
Chester is best known for its Stone Village Historic District, where you can wander along streets lined with greyscale granite homes. Downtown, you’ll find the Chester Village Historic District, showcasing a medley of Victorian, Colonial Revival, and Federal style architecture. From 19th-century stone cottages to wood-paneled carriage houses, Chester vacation rentals give you a chance to live and breathe history. Why not continue the theme with a ride on the Green Mountain Railroad, which steams past rising mountains, sparkling rivers, and historic towns?
Activities
Get the adrenalin pumping on Okemo Mountain
Rising above the nearby village of Ludlow, Okemo Mountain Resort is a 4-season outdoor playground. In winter, the mountain serves up some of Vermont’s best downhill skiing. When the snow melts Okemo’s Adventure Zone offers everything from ziplining and rock-climbing to segwaying and mountain biking. If you’re serious about your par, Okemo boasts a pair of 18-hole championship golf courses complete with spectacular mountain vistas. Just 45 minutes away, Manchester is a popular day trip. From touring the grand Hildene Estate to visiting the American Museum of Fly Fishing, the town is full of quirks.
Weather
Chester’s the gateway to Okemo Mountain Resort
Winter is arguably high season in Chester, when flocks of skiers descend on Okemo Mountain Resort. Planning a ski break in Vermont? Chester vacation rentals unlock access to a huge selection of properties just minutes from Okemo Mountain. From cozy log cabins to luxurious family-style farmhouses, you can create your very own apres ski scene. Visit in fall and Chester is showered in reds, yellows, and golds. Spring brings perfect weather for outdoor pursuits, especially if you’re planning on hiking Okemo Mountain.
Natural features
Mountains, forests, and Finger Lakes Fishing
Towering over 3000 feet high, Okemo Mountain dominates the landscape. If you’d rather escape the crowds, you’ll find off-the-beaten-track hiking trails in nearby state forests like Okemo and Proctor Piper. Hawks Mountain Wildlife Management Area is another backcountry favorite, with the chance to spot black bears and white-tailed deer. Both the Green Mountain National Forest (GMNF) and the Finger Lakes National Forest (FLNF) offer some of the state’s best fishing, though you’ll need to pick up a license before you cast a line.
How to get there
Transportation options to and around Chester
Fly into Springfield, VT (VSF-Hartness State), the closest airport, located 6.6 mi (10.7 km) from the city center. If you're unable to find a flight that fits your schedule, you could book a flight to Rutland, VT (RUT-Rutland Southern Vermont Regional), which is 25.2 mi (40.6 km) away.
How many vacation rentals are available around Chester, VT?
Our 2021 property listings offer a large selection of 961 vacation rentals around Chester. From 555 house rentals to 65 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.
Can I rent Houses in Chester?
Yes, of course. Vrbo has 555 Houses in Chester. Our other popular types of vacation rentals in Chester include:
- Cabins: 65 rentals available
- Condos/Apartments: 299 rentals available
- Cottages: 65 rentals available
But you can also enjoy a great stay in one of our other vacation rentals including Chalets and more.
Can I find a vacation rental with pool in Chester?
Yes, you can select your preferred vacation rental with pool among our 276 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.