Chester vacation rentals

Why visit Chester

• Outdoor adventures: Chester is perfect for outdoor enthusiasts, offering skiing, kayaking, and hiking experiences.
• Stunning landscapes: Explore breathtaking craggy peaks and serene central Vermont scenery.
• Charming small-town atmosphere: Enjoy the friendly vibe and cultural experiences unique to Chester.
• Diverse accommodations: Choose from cozy vacation homes, stylish condos, or charming cabins for a comfortable stay.
• Family-friendly activities: Visit Chester Park and explore local landmarks for enjoyable family outings.

Popular types of accommodation in Chester

Chester offers a variety of vacation rentals to suit every traveler's needs. Whether you're looking for a cozy private vacation home, a stylish condo, or one of the best Chester cabins, you'll find the perfect spot to unwind. With numerous options available, including charming cabins for rent and comfortable Chester hotels, your ideal getaway is just a click away. Explore all that Chester has to offer and make your vacation truly memorable.

• Houses: The top choice for visitors in Chester, these homes offer spacious and comfortable stays, perfect for families and groups.
• Condos: A popular option for travelers seeking convenience and amenities, condos provide a blend of comfort and accessibility.
• Cabins: Ideal for those wanting a rustic experience, cabins in Chester offer a cozy retreat surrounded by nature.
• Apartments: A practical selection for short stays, apartments provide a home-like atmosphere with essential facilities.
• Chalets: These charming lodgings combine alpine style and comfort, making them a delightful choice for visitors.**

Top attractions in and around Chester

Chester, Vermont, is an ideal destination for outdoor enthusiasts and families, offering a variety of adventures from skiing to friendly hikes. Explore stunning craggy peaks, enjoy kayaking experiences, and relax at Chester Park. The area features captivating landmarks and state parks, making it perfect for cultural experiences and family outings. Don't forget to check out local houses for rent for a comfortable stay while you discover all that Chester has to offer.

• Bonnie's Bundles Dolls: A charming attraction in Chester, offering a unique collection of handcrafted dolls that exude romantic vibes. Visitors can explore the artistry and craftsmanship behind each creation, making it a delightful stop for doll enthusiasts and collectors.
• Lake Rescue: Located 14 miles from Chester, this picturesque lake is perfect for outdoor activities and romantic getaways. Enjoy scenic views, a relaxing beach atmosphere, and opportunities for swimming, fishing, and picnicking.
• Jamaica State Park: Just 13 miles away, this national park features stunning scenery and a range of outdoor adventures. Hike through beautiful trails, discover waterfalls, and embrace the natural beauty of Vermont.

Things to do recommended for couples

Chester, Vermont, offers charming experiences for couples. Enjoy a scenic hike at the nearby Green Mountain National Forest, then unwind with a cozy dinner at a local eatery. Don't miss exploring the quaint shops and galleries in town for a delightful afternoon together.

Things to do recommended for families

Families visiting Chester, Vermont, can explore the scenic beauty of Okemo Mountain Resort, enjoy hiking trails suitable for all ages, and visit the local farmers' market for fresh produce and crafts. Don't miss the fun at the nearby Splashdown Park for a splash-tastic day.

Things to do recommended for groups

Explore the scenic Chester Village with its charming shops and eateries, or embark on a thrilling hike in the nearby Green Mountain National Forest. For a unique experience, consider a group visit to the local farmers' market for fresh produce and artisan goods.

What do I need to keep in mind when booking a vacation in Chester

When planning your trip—whether you're traveling with a group, enjoying quality time with family, bringing along your pets, or seeking extended stays—be sure to prioritize your preferences while filtering your options. Here are some helpful Vrbo booking tips to assist you.

• Traveling to Chester with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor area for group activities. Thankfully, you can easily filter for these options and more on Vrbo.
• Traveling to Chester with young kids: Traveling with young kids can present some challenges. It’s important to prioritize their comfort and safety, along with ensuring access to age-appropriate amenities, like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly attractions.
• Taking your pets with you to Chester: For many families, a trip just isn’t the same without their furry companions. If that resonates with you, explore Vrbo listings that welcome pets. Most of these pet-friendly properties offer feeding bowls and beds, ensuring that every member of your family feels at home.
• Planning for a long term stay visiting Chester: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Chester

Chester, Vermont, offers a delightful blend of adventure and relaxation, making it perfect for ski enthusiasts and budget travelers alike. Explore the charming small-town atmosphere, with nearby cities showcasing luxury and historical vibes. From the serene landscapes of central Vermont to friendly locals, your visit promises a memorable experience in this picturesque region.

• Ludlow: Ludlow is a charming city located 11 miles from Chester, offering visitors a perfect blend of outdoor adventure and small-town charm. Known for its excellent skiing opportunities, Ludlow is home to the popular Okemo Mountain Resort, where visitors can hit the slopes or enjoy snowboarding during the winter months. In addition to winter sports, the area features stunning lakes and mountains ideal for hiking and other outdoor activities in the warmer seasons. The nearby state park provides opportunities for camping and exploring nature, making Ludlow a year-round destination for adventure seekers.
• Springfield: Located a mere 6 miles from Chester, Springfield is a vibrant city that attracts travelers looking for an adventurous getaway. Like its neighboring towns, Springfield is renowned for its ski resorts and outdoor sports, making it a great spot for winter enthusiasts. Visitors can explore the scenic landscapes that encompass lakes and rolling mountains, perfect for hiking and picnicking during the summer months. The community offers a variety of local shops and restaurants, adding to the charm and experience of exploring this delightful New England town.
• Andover: Andover, a quaint village within the Chester area, is an ideal destination for those seeking a peaceful retreat with plenty of adventure. Just a short distance from Chester, Andover invites travelers to enjoy skiing and outdoor sports. Surrounded by picturesque lakes and majestic mountains, visitors can take in breathtaking views while hiking or enjoying water activities. The unique archipelago nearby provides additional exploration opportunities for nature lovers. Andover’s small-town atmosphere and access to outdoor recreation make it a hidden gem for a relaxing yet adventurous vacation.

Best time to go to Chester

If you're planning a trip to Chester, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from July to September, while off-peak times, like January to March tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	20.7°F (-6.3°C)	Light Rain	Mostly Cloudy	Slightly Low	Moderately High
February	22.6°F (-5.2°C)	Light Rain	Mostly Cloudy	Slightly Low	Moderately High
March	30.7°F (-0.7°C)	Light Rain	Mostly Cloudy	Slightly Low	Average
April	42.8°F (6.0°C)	Light Rain	Mostly Cloudy	Average	Moderately Low
May	55.8°F (13.2°C)	Light Rain	Mostly Sunny	Average	Moderately Low
June	63.1°F (17.3°C)	Light Rain	Mostly Sunny	Average	Average
July	69.3°F (20.7°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Slightly High	Moderately Low
October	48.6°F (9.2°C)	Light Rain	Mostly Sunny	Average	Average
November	36.1°F (2.3°C)	Light Rain	Mostly Sunny	Average	Average
December	27.3°F (-2.6°C)	Light Rain	Mostly Cloudy	Average	Moderately High

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming travel? Being flexible with your travel dates can be beneficial, as prices often fluctuate. Additionally, consider booking a longer stay, which can lead to considerable savings. To discover a Vrbo property that aligns with your budget, feel free to utilize our filters to narrow down options by price, location, and type of vacation rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board provides a convenient space for you to plan new trips, manage your ongoing plans, and organize your bookings. Your saved or booked properties are neatly categorized into Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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.