Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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$282 per night from 29 June to 30 June
NZ$282
29 June - 30 June
includes taxes & fees
8.2/10 Very Good! (437 reviews)
"This property had a lot of history to tell. The owner was very friendly and accommodating. The room was clean and the bed was comfortable. The restaurant in the hotel was very good too."

Reviewed on 14 June 2026

Fullerton Inn
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

Chester VT
9.8/10 Exceptional! (24 reviews)
"I had a great stay! Everything was as shown and described in the listing. My only advice is-if you are staying there during mud season make sure you have a AWD/4WD vehicle-the road to the property can get pretty bad."

Reviewed on 11 Mar 2026

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is NZ$1,049 per night from 13 July to 14 July
NZ$1,049
13 July - 14 July
includes taxes & fees
9.4/10 Exceptional! (586 reviews)
"If you're looking for a very comfortable stay in the quaint and historic town of Woodstock VT and don't worry about the expense, then the Woodstock Inn is the place for you!"

Reviewed on 16 June 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

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.