Become a host

Vacation rentals in Chester

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Chester

  • Total vacation rentals

    Explore 90 vacation rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

  • Verified guest reviews

    Over 4,050 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    90 of Chester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Chester rentals

  • 4.9 Average rating

    Chester stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Chester

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

1 of 1 pages1 / 1
Top guest favorite
A cozy tiny cabin, constructed with wooden beams and a sloped roof, is situated among tall trees. The porch features a railing, inviting seating, and a lantern. Sunlight filters through the foliage, casting a soft glow on the forest floor covered in pine needles.
Treehouse in Brookline
4.98 out of 5 average rating, 261 reviews

Glamping Cabin with Hot Tub on Flower Farm

<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

Top guest favorite
A cedar tiny home is positioned near a serene pond, surrounded by lush greenery. The structure features large windows and a porch, with picnic tables nearby. Reflections of the house can be seen in the calm water, enhancing the peaceful outdoor setting.
Cabin in Chester
4.99 out of 5 average rating, 78 reviews

Thistle House at Camp Greenwood Vermont with Sauna

Welcome to Thistle House, a custom-built cedar tiny home surrounded by seven acres of natural landscape in beautiful southern Vermont. Stargaze from the comfort of your bed, unwind in the barrel sauna, relax by the firepit overlooking your private pond or explore the many outdoor activities in the area. Ski Okemo, Magic and Bromley. Snowshoe or hike local trials and waterfalls, and enjoy quaint shops + restaurants. Pets welcome. Follow us on IG for updates and specials on stays: @campgreenwood.

Superhost
The charming treehouse is perched on stilts among lush greenery, with warm lights outlining the spacious deck. Large windows provide a view of the surrounding landscape, and a welcoming entrance is visible. The natural setting enhances the cabin's rustic appeal.
Treehouse in Londonderry
4.88 out of 5 average rating, 159 reviews

Riverbed Treehouse @hot tub & a new sauna & views!

The beautiful & brand new Riverbed Treehouse with private sauna and a stunning new hot tub! Views all day long and wildly awesome sunsets!! Stratton mountain is right at your toes with a babbling brook turned raging river in the Spring! Beautiful woods & trails to explore. Stunning ridge line off the ski trails of Magic Mnt!! Close to town for quick shopping & coffee shops! Xcountry ski or snowshoe or walk our groomed trails!! FAST WiFi, nature lovers & a birdwatchers paradise!! @bentapplefarm

Top guest favorite
Tiny home in Chester
4.99 out of 5 average rating, 116 reviews

Tiny A-Frame Rest House in Woods near Mountains

Newly built A-Frame getaway cabin built in the middle of the woods of Vermont. Unplug from it all at this special space surrounded by nature. Enjoy doing yoga and relaxing on the deck, remote working with fiber optic wifi, utilizing the fire pit to roast smores, or taking a walk around the walking paths on the property! There are also nearby hikes, swimming spots, skiing destinations, and drinking/eating spots! We are 35-40 minutes from Stratton, Mount Snow, Bromley, Okemo, and Magic Mountain!

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 381 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Superhost
The timber frame house is surrounded by dense trees, showcasing a natural setting. Large windows illuminate the exterior, providing glimpses of the interior. Sturdy wooden steps lead to the door, enhancing accessibility amid the forest environment.
Tiny home in Athens
4.92 out of 5 average rating, 243 reviews

Luxury “Tiny” House With Sauna (Timbery)

The Timbery: This is a new, fully handmade, timber frame "tiny" house featuring a custom Norwegian Sauna. The house is nestled in the forest, accessible by foot. With 17 vertical ft. of floor to ceiling windows, this property represents a unique experience to fully immerse yourself into nature. It is like lying down in a tent on the forest floor, except instead of wet sleeping bags and dirty hair, you enjoy a queen sized bed, in home theater, full kitchen, sauna and 71in soaking tub.

Guest favorite
The exterior of Bearfoot Cottage is highlighted, featuring a combination of wood and metal finishes. A spacious deck with steps leads to the entrance, framed by large windows. A fire pit sits nearby, complemented by comfortable seating arrangements on the gravel surface.
Tiny home in Chester
4.97 out of 5 average rating, 176 reviews

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

Guest favorite
Tiny home in Ludlow
4.96 out of 5 average rating, 96 reviews

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

Top guest favorite
A stone patio is illuminated by string lights, featuring a fire pit surrounded by three adirondack chairs in red, blue, and white. Lush greenery is visible in the background, creating a serene outdoor gathering space.
Apartment in Ludlow
4.96 out of 5 average rating, 124 reviews

Peaceful Ludlow base for exploring Okemo valley

Newly renovated, clean 1 BR apt. in historic house 2 blocks to town, 5 minute drive to Okemo, Buttermilk Falls, and 2 minute walk to the Ludlow Farmers Market. Enjoy complimentary coffee and local maple syrup while overlooking the town of Ludlow. Make yourself at home with a full kitchen/bath, wall-mounted flat screen TV, king bed, and comfortable futon. Free EV charging available. Kayaking, hiking, and golfing close by. We are dedicated to ensuring a top-notch experience!

Top guest favorite
A welcoming storefront features a wooden sign for Simon Pearce, accompanied by colorful pumpkins and vibrant yellow mums. The gray building showcases a green roof and large windows, with outdoor seating available on the patio. A blue sky with scattered clouds serves as the backdrop.
Apartment in Chester
4.93 out of 5 average rating, 164 reviews

Lovely 2 Bedroom Apartment w/deck & pond view

The perfect Vermont getaway. Lovely new apartment behind retail store on main road to Okemo and Killington for winter skiing and summer adventure. Bedroom, living room, bunk room, fully equipped kitchen, laundry and mudroom. Large deck with pond view, easy access to vacation sites, mountain hiking and biking, discovering Vermont small towns. Experienced, welcoming Airbnb Super Hosts providing all the amenities for a comfortable stay.

Top guest favorite
The exterior of an 1840s stone house is displayed, featuring a warm red door and large windows under a sloping roof. A well-maintained garden surrounds the entrance, and a tall tree provides shade. A gravel path leads to the house, with a visible stone wall along the yard.
Cottage in Chester
4.91 out of 5 average rating, 120 reviews

Quaint stone house!

⭐️ 2022 Rockingham Old House Award ⭐️ Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20 minutes to skiing and hiking, biking and the great outdoors are all around you! Less than 5 minutes to Vermont Country Store and make your way home through the Bartonsville Covered Bridge!

Top guest favorite
A patio area is visible, featuring a stone fire pit with colorful glass accents. Comfortable seating is arranged around the fire pit, with a large umbrella providing shade. The expansive green landscape stretches in the background, offering a view of distant mountains under a cloudy sky.
Apartment in Weathersfield
4.97 out of 5 average rating, 152 reviews

Cute VT Bungalow With 180 Degree View of NH

Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

Popular amenities for Chester vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Other great vacation rentals in Chester

Guest favorite
An outdoor space features a fire pit surrounded by four seating options, including two blue adirondack chairs and two black metal chairs. The area is set on a gravel surface with fallen leaves, complemented by a background of a blue farmhouse and trees.
Home in Chester
4.86 out of 5 average rating, 59 reviews

Historic 150-Year-Old Farmhouse | Jacuzzi included

Top guest favorite
Cabin in Grafton
4.94 out of 5 average rating, 16 reviews

Log cabin getaway

Top guest favorite
A sunroom is filled with natural light from large windows overlooking the outdoors. Various seating options are arranged, including a grey sofa and an armchair. A wooden table and chair set occupy one corner, while a dog stands near the windows, enjoying the view.
Home in Baltimore
5 out of 5 average rating, 23 reviews

Tarbell Farm on the hill top

Top guest favorite
A charming restored house with a distinctive pink exterior is framed by lush greenery. The front door is painted a vibrant teal, complementing the white trim and windows. A tall tree stands beside the home, adding to the serene outdoor setting.
Home in Grafton
4.94 out of 5 average rating, 18 reviews

Pettengill Schoolhaus scenic 2 min to main village

Top guest favorite
A view from a deck presents a lush green yard, framed by trees and rolling hills in the background. The expansive grass lawn gently slopes downward, and a solitary tree stands prominently on the left, set against an overcast sky.
Barn in Town of Rockingham
5 out of 5 average rating, 40 reviews

Quiet Country Retreat

Guest favorite
A modern A-frame cabin is set among lush greenery, featuring a striking wall of windows that showcases the interior. The design includes sloped roofs and a mix of natural materials, blending harmoniously with the surrounding landscape.
Cabin in Ludlow
4.98 out of 5 average rating, 97 reviews

A-Frame Window Wall Okemo views w/ Hot Tub & Sauna

Guest favorite
Home in Chester
5 out of 5 average rating, 5 reviews

Renovated 3-BR Cabin Near Okemo

Top guest favorite
A spacious kitchen area is highlighted by exposed wooden beams and a large dining table surrounded by wooden chairs. The floor features warm wood tones, while a colorful rug adds an inviting touch. Natural light streams in through the glass door and windows.
Home in Springfield
5 out of 5 average rating, 79 reviews

1794 Vermont Home

When is the best time to visit Chester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 936ﺩ.ﺇ 951ﺩ.ﺇ 826ﺩ.ﺇ 679ﺩ.ﺇ 679ﺩ.ﺇ 679ﺩ.ﺇ 679ﺩ.ﺇ 723ﺩ.ﺇ 709ﺩ.ﺇ 826ﺩ.ﺇ 918ﺩ.ﺇ 955
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

Frequently Asked Questions

  • What are the best places to stay in Chester?

    Stays in historic downtown buildings, classic Vermont homes, and rural cabins are often recommended. Neighborhoods near local shops and parks provide convenient access to main attractions.

  • What are the best things to do in Chester with kids?

    Kids can enjoy public parks, craft workshops, and exploring antique shops as family-friendly outings. Seasonal festivals and markets often include activities for children, such as games and interactive demonstrations.

  • What are some of the best things to do in Chester?

    Explore historic downtown streets, browse antique shops, and visit local art galleries or museums. Outdoor activities like hiking, walking in parks, and attending craft markets are frequently suggested.

  • How is the weather in Chester?

    Chester has cold, snowy winters with temperatures ranging from 13–32°F (-11–0°C), and warm summers from 57–81°F (14–27°C). Spring and fall bring milder temperatures and occasional rain, so layers and a waterproof jacket are helpful.

  • When is the best time to visit Chester?

    Late spring through early fall is often recommended for comfortable temperatures, outdoor activities, and seasonal festivals. Autumn draws visitors for colorful foliage and local harvest celebrations.

  • What are the best places to visit in Chester?

    Downtown Chester is known for its historic stone buildings and quaint shops, while local parks and art studios provide opportunities to discover regional culture. Museums and craft fairs are also often recommended.

  • What are some hiking trails in Chester?

    Chester has forested hiking trails, walking paths in public parks, and scenic routes through rural landscapes. Trailheads around town provide options for easy to moderate outdoor adventures.

  • What are some family activities we can do in Chester?

    Explore public parks for picnics, visit local museums or art workshops, and enjoy seasonal festivals featuring crafts and live music. The area has family-friendly walking routes and recreational spaces.

  • What are some of the best day trip ideas from Chester?

    Day trips often include exploring nearby villages with covered bridges, visiting regional museums, or hiking in natural reserves around the area. Local farms and outdoor recreation spots add variety to itineraries.

  • Are there any pet friendly accommodations available in Chester?

    Many accommodations in and around Chester welcome pets, particularly vacation rentals and cabins. The area has parks where guests can take dogs for a walk or play outdoors.

  • What are some local tips for visiting Chester?

    Locals suggest browsing the shops early for quieter experiences, and packing comfortable shoes for exploring main streets. Seasonal festivals and farmers markets are frequently suggested, especially for discovering local foods and crafts.

  • What is Chester known for?

    Chester is known for its historic architecture, vibrant local arts scene, and community markets. Maple products, handcrafts, and scenic surroundings with classic Vermont landscapes are part of its distinct character.

  • What are the best hidden gems to explore in Chester?

    Chester has historic stone buildings downtown, antique shops tucked among classic storefronts, and locally owned art galleries that showcase regional talent. Around town, small parks and craft studios are often recommended for quieter moments.

  • What are the best foods to try in Chester?

    Vermont cheddar, maple syrup treats, and hearty farmhouse breads are often recommended. Local restaurants serve dishes featuring seasonal produce, and bakeries have pies and pastries rooted in regional traditions.

  • What should I bring for a trip to Chester?

    Pack layers for changing temperatures, a waterproof jacket, comfortable walking shoes, and any outdoor gear depending on activities planned. An umbrella and reusable water bottle are handy for wandering town or local trails.

  • What is the nightlife in Chester like?

    Nightlife in Chester tends to be relaxed, with local taverns, pubs, and casual dining spots around downtown. Some venues host live music or trivia nights, creating welcoming spaces for visitors and residents.

  • What are the most popular events or festivals in Chester?

    Chester has seasonal festivals with crafts, art, and live music, as well as markets celebrating local foods. Fall events featuring foliage and community gatherings are frequently suggested in the area.

  • Are there family friendly vacation rentals in Chester?

    Chester has a variety of family-friendly vacation rentals, including classic Vermont homes and spacious cabins. Many are located near parks, shops, and outdoor spaces, making it easy for families to explore together.

Destinations to explore

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