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Holiday rentals in Chester

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Quick stats about holiday rentals in Chester

  • Total holiday rentals

    Explore 80 holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at £45 per night before taxes and fees

  • Verified guest reviews

    Over 3,530 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    80 of Chester holiday rentals include wifi 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 holiday rentals in Chester

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

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Top guest favourite
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, 81 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.

Top guest favourite
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
4.95 out of 5 average rating, 19 reviews

Pettengill Schoolhaus scenic 2 min to main village

Our lovingly restored gem is located >2 miles outside the historic town of Grafton, Vermont. A lovely walk or 10 min. bike ride from Grafton Inn & Tavern (live music!), General Store, shops, museums, tennis. >3 miles to the Outdoor Center hiking, biking, Nordic skiing & swimming. Direct access to the VAST trail system and easy drive to Okemo, Stratton & Lowell Lake. The house is a well appointed 2 bedrooms, 2 baths. Guests love the spacious common areas, inside and out, all in the school theme.

Guest favourite
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, 163 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 favourite
Tiny home in Chester
4.98 out of 5 average rating, 125 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!

Superhost
An aerial view captures a cozy cottage situated along the Connecticut River. Lush greenery borders the water, and a small pathway leads to the cottage. A boat glides along the river, highlighting the serene setting surrounded by forests and rolling hills.
Guest house in Springfield
4.84 out of 5 average rating, 402 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

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
4.91 out of 5 average rating, 245 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 favourite
A snow-covered landscape surrounds the historic farmhouse and attached barn. The yellow house features a rounded wall and is partially obscured by snowdrifts. The red barn is visible to the right, under a clear blue sky, creating a serene winter scene.
Home in Chester
4.8 out of 5 average rating, 100 reviews

Vermont 1828 Reunion House, near Okemo

The Vermont 1828 Reunion House, close to Okemo is a spacious historic vintage ski lodge and farmhouse with 2 kitchens, 8 bedrooms, 4 baths, & a quintessential Vermont character. Excellent for gatherings & family reunions. Linens & towels provided, beds made. 10 acres, meadow & hidden pond. . A new automatic sprinkler system was installed in 2024 & the house complies with all safety regulations & certified by the town of Chester. Must be 25 years to rent. Long term rentals possible.

Guest favourite
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, 178 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!

Superhost
Home in Chester
4.87 out of 5 average rating, 99 reviews

Charming Chester Farmhouse Near VT Slopes

Unplug at our spacious 4-bed Chester farmhouse, a four-season retreat minutes from Okemo, Magic & Bromley. Highlights: *Chef’s kitchen & coffee bar *Fast Wi-Fi, dedicated workspace & Smart TV *Spacious backyard for dining & stargazing *Easy 10–20 min to skiing, hiking & local towns *Pet-friendly, family-ready Spend your days hiking, swimming, leaf peeping, or exploring nearby towns. In winter, hit the slopes, then gather for games and a movie. Book your Vermont getaway today!

Top guest favourite
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.
Flat in Ludlow
4.96 out of 5 average rating, 126 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 favourite
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.
Flat 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.

Guest favourite
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
4.89 out of 5 average rating, 122 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!

Popular amenities for Chester holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Chester

Top guest favourite
Home in Chester
5 out of 5 average rating, 10 reviews

Modern 3BR/3BA Main+River Retreat | Ski Okemo

Guest favourite
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
4.87 out of 5 average rating, 60 reviews

Historic 150-Year-Old Farmhouse | Jacuzzi included

Top guest favourite
Home in Springfield
5 out of 5 average rating, 52 reviews

Scandinavian Serenity Close to Okemo

Top guest favourite
Cabin in Grafton
4.94 out of 5 average rating, 17 reviews

Log cabin getaway

Superhost
Treehouse in Jamaica
5 out of 5 average rating, 3 reviews

The Treehouse at Frog Pond Farm

Top guest favourite
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, 43 reviews

Quiet Country Retreat

Top guest favourite
Tiny home in Ludlow
4.96 out of 5 average rating, 98 reviews

Alpine Reflection + Hot Tub

Guest favourite
Home in Andover
5 out of 5 average rating, 29 reviews

Mountain Retreat | Hot Tub | 9 Acres | Views

When is the best time to visit Chester?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price£190£193£168£138£138£138£138£147£144£168£187£194
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

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