Chester Vacation Rentals, Vermont: house rentals & more

Discover a selection of 33 homes and other vacation rentals in Chester that are perfect for your trip. Vacation rentals offer the best amenities for you and your friends, family, or even pets, such as parking and a fireplace. You're sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

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Find the best place to stay - Chester

Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort

Sleeps 6 · 4 bedrooms · 2 bathrooms

Top rated rentals - Chester

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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.

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?

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.

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.

Traveling 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 can also fly into Lebanon, NH (LEB-Lebanon Municipal), which is 28.8 mi (46.4 km) away.

Frequently asked questions

What is the best area to stay in Chester when booking a vacation rental?

If you're planning a vacation in Chester, Chester Depot is among the most sought-after locations to stay. No matter your style of travel, Vrbo is bound to have a vacation property here that's right for you.

What is the most popular type of vacation rental accommodation in Chester?

Houses are the most popular style of vacation rental in Chester, according to our data. Even if you have a different idea about what you want, Vrbo has properties in many shapes and sizes. Browse our options to find your ideal match.

How much does it cost to rent a vacation rental in Chester?

A number of factors can affect the price of a vacation rental in Chester, such as the type of property, length of stay and season. But, all of our vacation homes have one thing in common — unbeatable value. Just add your travel dates to find your ideal fit.

How much does it cost to rent a beach house in Chester?

The average price for a vacation rental close to the beach in Chester will depend on when you're going and the type and size of property you're looking for. You can easily find prices on Vrbo by entering the dates you'll be traveling. Then use the filter tool to choose the number of bedrooms and amenities important to you, such as a pool, air conditioning and WiFi.

Are there pet-friendly vacation rentals in Chester?

Pack up a suitcase for the pooch in your life because Chester has 35 vacation rentals that throw open their doors to pets. Let your furriest pal join in with the family fun at one of our pet-friendly vacation rentals on Vrbo. Simply enter your travel dates then check our "Pets allowed" filter box.

Can I rent a house with a pool in Chester?

Pack your swimwear and inflatable flamingo, because there are six houses with a private pool in Chester. Unwind at one of these sought-after vacation rentals and let every day be a pool day. Simply enter your dates into Vrbo, then use the "pool" filter to find the ideal place for a splashing good time!

What are popular rental amenities in Chester?

A water view, ski-in/ski-out facilities and a sauna are rated the most popular rental amenities in Chester. Whether you're taking to the road by yourself, with your other half or a group of friends, Vrbo will help you find a vacation rental that matches your style with all the conveniences you're looking for.

Are there large group vacation rentals in Chester?

Chester has 11 vacation properties that can host 10 or more guests. These stays come with plenty of space to share good times with friends and family.

Are there vacation rentals in Chester that welcome kids?

Gather the whole crew for an adventure in Chester at one of our 35 family-friendly vacation properties. A lot of these stays come with amenities that are great for getaways with the little ones, like laundry facilities, extra bedrooms and patios. Simply click on the "Properties good for families" filter box and choose your favorite option.

What are the top attractions for families in Chester?

If you're seeking some fun for the whole family close to the heart of Chester, make sure to visit DaVallia Art & Accents.

Are there one-bedroom vacation rentals in Chester?

Yes, you can take your pick from five one-bedroom rentals in Chester. Whether you'd prefer a cozy chalet or a cabin, our one-bedroom properties are perfect if you don't require a huge amount of space. One of the major perks of having your own pad? You won't have to share your trip with strangers.

Can I find two-bedroom vacation rentals in Chester?

Take off with your besties and enjoy a relaxing escape in one of the four two-bedroom vacation properties Chester has to offer.