Chester Holidays

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Chester Holiday

Things to do near Chester

Shopping

For a delightful shopping experience in Chester, visit the Vermont Country Store and My Minds Design, both located 9.7km away. If you're up for a drive, check out the West River Farmers Market, situated 17.7km from Chester, where you can enjoy a lively local atmosphere.

Recreation

In Chester, explore the Weston Playhouse, a charming theatre 16.1km away, offering a delightful mix of romance and culture. For outdoor enthusiasts, the Crown Point Golf Course, situated 12.9km from Chester, provides a scenic golfing experience, while the Fox Run Golf Course, 19.3km away, promises more sports-filled enjoyment.

Adventure

Experience thrilling adventures at Viking Nordic Center, a ski field 16.1km from Chester, perfect for skiing enthusiasts. For a lift in excitement, head to A Ski Lift, located 17.7km away, offering sweeping views and adrenaline. Don’t miss the scenic flights at Morningside Flight Park, 19.3km from Chester.

Nightlife

Chester's nightlife offers a charming mix of cosy pubs and local eateries. Visit the Chester Tavern for a warm atmosphere and hearty meals, or enjoy live music at the local concert venue. The town's friendly vibe makes it a delightful spot for a relaxed evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions near Chester

Chester, Vermont, is perfect for skiing, adventure, and sports holidays, offering a variety of parks, landmarks, and national/state parks. Enjoy outdoor activities, cultural experiences, and family-friendly attractions, including the Chester Town Hall, Chester Racecourse, and the beautiful gardens. Don't miss a visit to the historic town of Chester for a unique experience amidst stunning scenery.

  • Vermont Museum of Mining and Minerals: This engaging natural history museum, located 9.7km from Chester, showcases Vermont's rich mining history and unique mineral specimens. It's a family-friendly spot where you can learn about geology and the state's cultural heritage through interactive exhibits.
  • Baltimore Covered Bridge: Situated 11.3km away, this enchanting historic place offers a picturesque view and a glimpse into Vermont's architectural heritage. It's a fantastic spot for photography and appreciating the craftsmanship of covered bridges.
  • Weston Priory: A serene monastery located 17.7km from Chester, Weston Priory provides a peaceful retreat. Visitors can experience the tranquil atmosphere and learn about the monastic life, enriched by its beautiful surroundings.

Best time to go to Chester

The best time to visit Chester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.7°F (-6.3°C)Light RainMostly CloudySlightly LowSlightly High
February22.6°F (-5.2°C)Light RainMostly CloudySlightly LowSlightly High
March30.7°F (-0.7°C)Light RainMostly CloudySlightly LowAverage
April42.8°F (6.0°C)Light RainMostly CloudyAverageSlightly Low
May55.8°F (13.2°C)Light RainMostly SunnyAverageSlightly Low
June63.1°F (17.3°C)Light RainMostly SunnyAverageAverage
July69.3°F (20.7°C)Light RainMostly SunnySlightly HighAverage
August67.3°F (19.6°C)Light RainMostly SunnySlightly HighAverage
September60.3°F (15.7°C)Light RainMostly SunnySlightly HighAverage
October48.6°F (9.2°C)Light RainMostly SunnyAverageSlightly High
November36.1°F (2.3°C)Light RainMostly SunnyAverageSlightly Low
December27.3°F (-2.6°C)Light RainMostly CloudyAverageAverage

Tips to save on your trip to Chester

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Chester during the low season (April to May and November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Our pick of the best Chester Hotel Deals

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
The price is NZ$240 per night from 24 Mar to 25 Mar
NZ$240
24 Mar - 25 Mar
includes taxes & fees
8/10 Very Good! (424 reviews)
Yes, little guests easy parking spaces. Restaurant staff were pleasant. Heat didn’t appear until 11PM. A tad chilly. Room was clean.

Reviewed on 20 Mar 2026

Fullerton Inn
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
The price is NZ$266 per night from 30 Mar to 31 Mar
NZ$266
30 Mar - 31 Mar
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Clean, comfortable and quiet. Great retreat for skiers. Nice hot tub, comfy beds and convenient parking.

Reviewed on 19 Mar 2026

Pointe at Castle Hill Resort
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is NZ$658 per night from 22 Mar to 23 Mar
NZ$658
22 Mar - 23 Mar
includes taxes & fees
9.2/10 Wonderful! (569 reviews)
Excellent!!

Reviewed on 18 Mar 2026

Woodstock Inn & Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

What to do in Chester

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