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$258 per night from 1 Sept to 2 Sept
NZ$258
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very good! (446 reviews)
"The rooms are very clean. I had no problem with any of that. We went downstairs and told the manager that the bathroom sink was not draining and he said he would take care of it and he did we got back from where we had gone for the day it was working. We had our breakfast between eight and 11 is ..."

Reviewed on 3 Aug 2026

Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is NZ$1,066 per night from 1 Sept to 2 Sept
NZ$1,066
1 Sept - 2 Sept
includes taxes & fees
Woodstock Inn & Resort
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd Keene NH
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 1 Sept to 2 Sept
NZ$218
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"Very clean modern hotel with exceptional staffing! My wife and I were extremely pleased."

Reviewed on 3 Aug 2026

Keene Elm City Hotel, an Ascend Collection Hotel
See all 3,081 properties in Chester
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.

Stay near popular Chester attractions

DaVallia Art & Accents

10.0/10 (2 reviews)
This Vermont art haven showcases fine local art and handcrafted furniture in thoughtfully designed spaces. Browse both the Art Boutique and 39 North Gallery to experience indoor exhibits and outdoor sculpture gardens.
See properties

What to do in Chester

Colonial Flintlock Musket Experience

Colonial Flintlock Musket Experience

NZ$223
per adult
100% of travellers recommend
Colonial Flintlock Musket Experience
See all activities in Chester

Frequently asked questions

How much does a Chester holiday package cost?
You can grab a holiday package to this destination on Expedia. However, how much your holiday to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
If you'd like to snag a cheap Chester holiday package, consider planning a trip in March, May and June. You'll generally find better rates on accommodation and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Chester?
Usually, a handful of days is enough to see the major sights during your Chester holiday. However, if you want to have more time to chill out or take day trips, consider extending your itinerary.
How to find the best Chester package deals?
Bagging a cheap Chester package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most affordable Chester package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chester holiday as a package?
You can enjoy significant savings on your Chester escape by booking a customised holiday package. Click on the "Package" heading, then select your travel dates and destination to view the best airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Chester?
If you have your Chester travel dates finalized, book early to score some outstanding deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Chester?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the activities available will also help you decide when to visit Chester.
  2. Figure out your budget: Make sure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodation will probably be the biggest expense during your trip to Chester.
  3. Decide how long to go for: Now that you're more familiar with Chester, you can work out the right length of your break. Pull together a rough itinerary and allocate enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customised Chester holiday package.

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.