Chester Vacations from $686

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Your Chester Vacation

Excellent adventures await when you reserve a Chester vacation package. Whether you're a history buff, art enthusiast or just a traveler who loves to experience new places, there's something for everyone in this lively city. Need some ideas on what to see or do first during your trip to Chester? Don't miss leading attractions like DaVallia Art & Accents. Your ultimate Chester vacation is just clicks away. Search flights, accommodations and more on Expedia for a trip that's tailored to suit your travel style.

The Latest Chester vacation packages

Price found within the past 48 hours. Click for updated prices.
The Covered Bridge Inn
Latchis Hotel
Colonial Motel And Spa
The One Cat B&B
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Discover the most popular places to visit in Chester

Chester Hotel Deals

Fullerton Inn

Fullerton Inn

2.5 out of 5
40 The Common Chester VT
Fully refundableReserve now, pay when you stay
$129 nightly
The price is $141 total per night from Jan 13 to Jan 14
$141 total
Jan 13 - Jan 14
Total with taxes and fees
8/10 Very Good! (408 reviews)
Where to start!? If you like small town vibe with all the necessities close by I highly suggest this location. The building is absolutely gorgeous and is located on a little “service road” with a few shops and stores in easy walking distance. From front desk to restaurant staff, everyone was fun, ...

Reviewed on Jan 6, 2026

Fullerton Inn
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$359 nightly
The price is $395 total per night from Jan 19 to Jan 20
$395 total
Jan 19 - Jan 20
Total with taxes and fees
9.2/10 Wonderful! (559 reviews)
Luxurious and friendly resort! Loved it

Reviewed on Dec 18, 2025

Woodstock Inn & Resort
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
$159 nightly
The price is $173 total per night from Jan 25 to Jan 26
$173 total
Jan 25 - Jan 26
Total with taxes and fees
8.8/10 Excellent! (951 reviews)
Clean, nice pool and hot tub, and good price!

Reviewed on Jan 11, 2026

Pointe at Castle Hill 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.

Find the Best Chester Vacation Packages

Things to do near Chester

Chester, Vermont, is an excellent destination for those seeking adventure and winter sports. Enjoy skiing at local ski resorts and explore inviting ski areas. For those interested in a well-rounded vacation, Chester offers opportunities for day trips and unique tours, making it perfect for both ski enthusiasts and families looking for a fun getaway. Don't forget to check out the charming local attractions to enhance your visit.

Shopping

In Chester, you can visit the Vermont Country Store, a charming spot only 6 miles away, perfect for unique gifts. If you're up for a drive, check out the West River Farmers Market, located 11 miles away, or the Green Mountain Sugar House, which is 13 miles from Chester.

Recreation

The Weston Playhouse offers a captivating theater experience with a blend of culture and entertainment, perfect for a romantic evening. For golf enthusiasts, Fox Run Golf Course provides a beautiful outdoor setting to enjoy the sport. The Ice House Ice Skating is ideal for relaxation and wellness, featuring a fun skating environment.

Adventure

Experience thrilling skiing at Okemo Mountain Resort, located 11 miles from Chester, where you can enjoy snowy slopes and vibrant sports vibes. For a breathtaking view, take a scenic flight at Morningside Flight Park, situated 12 miles away, and feel the rush of adventure while soaking in the stunning landscape.

Nightlife

Chester, Vermont, offers a cozy nightlife atmosphere with local taverns like The Fullerton Inn, where you can enjoy craft beers and live music. For a relaxed evening, visit the Chester Village Pub, known for its warm ambiance and friendly locals, perfect for winding down after a day of exploring.

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

Find the best attractions in and around Chester

Chester, Vermont, is perfect for ski enthusiasts and adventure seekers alike. Explore its beautiful parks, national and state parks, and captivating history museums. Whether you're looking for outdoor activities, cultural experiences, or family-friendly fun, Chester offers a variety of attractions that cater to every type of traveler, ensuring a memorable vacation in this charming town.

  • DaVallia Art & Accents: Immerse yourself in the vibrant arts scene at DaVallia Art & Accents, a local gallery showcasing unique works from talented artists. The gallery's warm, cultural ambiance invites you to explore and appreciate various art forms, making it a perfect spot for art lovers.
  • Lowell Lake State Park: Just 9 miles from Chester, Lowell Lake State Park offers breathtaking scenery and outdoor adventure. Enjoy hiking, picnicking, and wildlife watching in a serene natural setting, where the beauty of Vermont's landscape can be fully appreciated.
  • Bonnie's Bundles Dolls: Discover the charming world of Bonnie's Bundles Dolls, where nostalgia meets craftsmanship. This delightful attraction features handcrafted dolls that evoke romantic memories, making it a perfect stop for collectors and families alike.

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

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chester.
  • Consider traveling during the off-peak season (typically April to May and November) for more affordable package holidays to Chester.
  • 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.

Chester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lebanon Municipal Airport (LEB)
Population
3,000
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Weston Playhouse, Weston Priory and Fox Run Golf Course

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Frequently asked questions

How much does a Chester vacation package cost?
You can grab a vacation package to this destination from $686 on Expedia. However, how much your vacation to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
March, April and August are the best times to look for cheap Chester vacation packages. Traveling in quieter months means you can usually find reduced prices on flights and hotels.
How many days is enough for Chester?
Typically, a handful of days is enough to go to the top attractions during your Chester vacation. However, if you want to have time to chill out or go on day trips, think about 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," "Traveler 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 vacation as a package?
You can enjoy significant savings on your Chester escape by booking a customized vacation 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 vacation 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 traveling on a whim.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the cost of your Chester trip over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.

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