Vacation rentals in Chester
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Top-rated vacation rentals in Chester
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Vermont Mirror House
Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!
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.
Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba
Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants
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
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!
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!
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!
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!
Schoolhouse Spa Retreat on a Vermont Farm
Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.
Lovely 1-Bedroom condo with indoor fireplace!
This cozy condo is exactly what a close group of 4-5 people need for a wonderful ski experience. Located centrally in the beautiful town of Ludlow this location is close to everything you could want. It sits on the bus route for Okemo Mountain, and is walkable to groceries, restaurants and bars. "Eight Oh Brew" tap house is located on the base floor of the building. This location has free onsite parking, free firewood and coin laundry machines.
LUXE Forest Retreat
Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.
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.
Popular amenities for Chester vacation rentals
Other great vacation rentals in Chester
Charming Vermont Schoolhouse
Guest house with attention for detail
Charming New England Cape
Sunny Summer Cabin | Scenic Views + Deck
Historic Luxury Loft
Vermont Ski and Stay
Charming cottage on country road
The Looking Glass, a modernistic escape
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R4,266 ZAR | R4,333 ZAR | R3,764 ZAR | R3,095 ZAR | R3,095 ZAR | R3,095 ZAR | R3,095 ZAR | R3,296 ZAR | R3,229 ZAR | R3,764 ZAR | R4,182 ZAR | R4,349 ZAR |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°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.
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 R1,004 ZAR 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!
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