Where to stay around Chester?

Our 2019 property listings offer a large selection of 992 vacation rentals near Chester. From 448 Houses to 325 Condos/Apartments, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Chester for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Chester?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Chester:

  • Okemo Mountain Resort: 178 vacation rentals
  • Stratton Mountain Resort: 101 vacation rentals
  • Killington Ski Area: 271 vacation rentals
  • West Woodstock: 20 vacation rentals
  • Bromley Mountain: 520 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

Can I rent Houses in Chester?

Yes, of course. HomeAway has 448 Houses in Chester. Our other popular types of vacation rentals in Chester include:

  • Condos/Apartments: 325 rentals available
  • Bungalows: 58 rentals available
  • Cabins: 58 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cottages and more.

Can I find a vacation rental with pool in Chester?

Yes, you can select your preferred vacation rental with pool among our 281 vacation rentals with pool available in Chester. Please use our search bar to access the selection of vacation rentals available.

    A slice of New England in Chester

    With its red-brick buildings and characterful high street, Chester embodies everything that’s great about America’s New England communities. It’s now listed on the National Register of Historic Places, which makes it a great place to discover history, culture, and the Vermont countryside. The atmosphere is unique, so why not stay local with downtown Chester vacation rentals housed in beautifully renovated Victorian buildings? Beyond its downtown charm, Chester serves as the gateway to Okemo Mountain Resort, as well as some of Vermont’s most beautiful national forests.

    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.

    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?

    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.

    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.