Chester Vacations from $748

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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.
Latchis Hotel

Latchis Hotel

2.5 out of 5
Price was $876, price is now $748 per person
$748
per person
Dec 27 - Jan 1
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
8.6/10 Excellent! (1,011 reviews)

Vikings Villages Resort

Vikings Villages Resort

2 out of 5
Price was $1,177, price is now $921 per person
$921
per person
Dec 27 - Jan 1
found 7 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
10/10 Exceptional! (250 reviews)

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $2,085, price is now $1,682 per person
$1,682
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.8/10 Excellent! (1,002 reviews)
The manager and owners do not help with any situation. My room was not clean. Pubic hairs in the shower. Hairs all over the floor, spiders, crumbs all over the valet. Baseboards were covered in filth. No one would return my calls, emails or text messages.

Reviewed on Oct 30, 2026

Luxury 6br Solitude Ge- Indoor Bball Court, Private Tub 6 Bedroom Home by RedAwning

Luxury 6br Solitude Ge- Indoor Bball Court, Private Tub 6 Bedroom Home by RedAwning

3.5 out of 5
Price was $21,100, price is now $18,494 per person
$18,494
per person
Dec 20 - Dec 26
found 24 hours ago
Roundtrip non-stop flight included
Washington (WAS) to Springfield (VSF)
No reviews

Jackson Gore Village, A Vail Resorts Property

Jackson Gore Village, A Vail Resorts Property

3 out of 5
Jackson Gore Base Area
Price was $2,482, price is now $2,184 per person
$2,184
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Springfield (VSF)
8.6/10 Excellent! (949 reviews)

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Stay near popular Chester attractions

Bonnie's Bundles Dolls

7.6/10 (4 reviews)
This historic Vermont studio showcased handcrafted cloth dolls with embroidered faces and calico clothing. Visitors treasured personal interactions with artist Bonnie Watters and stories behind her creations.
See properties

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 Nov 10 to Nov 11
$141 total
Nov 10 - Nov 11
Total with taxes and fees
Fullerton Inn
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3 out of 5
698 VT-11 Chester VT
Fully refundableReserve now, pay when you stay
$197 nightly
The price is $215 total per night from Nov 16 to Nov 17
$215 total
Nov 16 - Nov 17
Total with taxes and fees
9.2/10 Wonderful! (130 reviews)
"Breakfast was very nice and staff very friendly… unfortunately it is not very accessible if you have walking difficulties … all the bedrooms are on the second floor and there are no elevators… l wish l had known this before l had booked the room …. we stayed 1 night even though we had reserved 2 ..."

Reviewed on Oct 8, 2026

Stone Hearth Inn and Eatery
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! (25 reviews)
"This is an adorable and cozy cabin surrounded by nature - from which you can hear a soothing stream from your window. If you are looking for a place to restore in nature and unplug "glamping-style" - yet close to shops/coffee/outings, etc., - this little blue cabin is the perfect spot. I liked that ..."

Reviewed on Jul 6, 2026

Get rates
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
See all 3,105 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.

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

What's the best vacation package for Chester?
For families seeking a Chester vacation package, a stay at Stone Hearth Inn and Eatery (rated 8.8 out of 10) offers a welcoming base. This inn provides family rooms and a game room, making it convenient for those traveling with children, and travelers often praise the excellent staff and overall great experience. It's also about 10 miles from Okemo Mountain Resort, a popular ski destination.

If you're looking for a comfortable and highly-rated Chester vacation package, Stone Hearth Inn and Eatery also stands out. Located about 1 mile from central Chester, this property is noted for its beautiful location and great breakfast, with travelers highlighting the excellent staff. It's a strong choice for those wanting a cozy retreat after a day on the slopes.
How can I save money on a Chester vacation package?
When you bundle, you can save up to 30%*. To save money on a Chester package, consider traveling during the quieter months or be flexible with your dates to find more options. Bundling your flights and hotel together often unlocks savings compared to booking separately. *Members only. Savings vary.
What are the top things to do in Chester?
A Chester vacation offers a range of outdoor activities and local attractions, reflecting its character as a ski destination outside a city:

Browse and book things to do in Chester on Expedia.
Do you need to rent a car in Chester, or is public transport enough?
For a Chester vacation package with flights, a rental car is highly recommended for exploring the area. As a ski destination outside a city, attractions and resorts are often spread out. Chester is served by Vermont routes 10, 11, 35, and 103, with Interstate 91 accessible via a nearby exit, making road travel the primary way to get around.

While some hotels in areas like Chester Depot are conveniently located near ski resorts such as Okemo Mountain Resort, Mount Snow, and Magic Mountain Ski Resort, having a car provides the flexibility to visit various slopes, explore local towns, and access other outdoor activities at your own pace.
Are Chester vacation package hotels conveniently located?
Chester vacation package hotels offer a mix of central and resort-proximate locations, fitting its character as a ski destination outside a city. For example, Stone Hearth Inn and Eatery, rated 8.8 out of 10, is located about 1 mile from central Chester and offers amenities like free breakfast; travelers often praise the excellent staff and beautiful location.

The Chester Depot neighborhood, which has around 15 hotels, places you conveniently near popular ski resorts like Okemo Mountain Resort. This means you can choose a package that keeps you close to the town's core or one that prioritizes access to the slopes.
Can I change or cancel my Chester vacation package if my plans change?
Yes, you can cancel your vacation package via your itinerary page on Expedia or by contacting customer service. Remember that some packages are fully refundable, but the details vary based on each unique booking. A fully refundable package may depend on how far out from the travel dates you're canceling and what airline you are traveling with.
Do One Key members get extra savings when booking Chester vacation packages?
Yes, members who join our free One Key™ travel rewards program can instantly unlock additional savings and save 10% or more on over 500,000 stays worldwide with Member Prices and over 1 million car rentals.
Does Expedia offer Book Now, Pay Later Chester vacation packages?
Yes, with Expedia's Book Now, Pay Later option, powered by Affirm, you can spread the cost of your Chester vacation over 3, 6, or 12 months. With no late payment fees or hidden costs, it's easy to secure your ideal vacation package as soon as you spot it.
How do I find last-minute vacation packages to Chester?
To find last-minute vacation packages to Chester, explore the last-minute deals section for the latest package offers, including flights, departing in the coming weeks. Being flexible with your travel dates and hotel preferences can help you secure the best prices.
How does free cancellation work on Chester vacation packages?
Free cancellation on a Chester vacation package depends on the specific hotel and rate combination you book. Many bookings allow free cancellation up to a stated deadline (often a few days before travel) where eligible. Read the cancellation terms carefully when reviewing the package, and visit Expedia help center for further details.
Is it cheaper to book a Chester vacation as a package or separately?
Booking flights and hotels together can unlock lower overall prices. Better still, you can tailor your Chester getaway to match your exact preference. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
Why should I book my Chester vacation package with Expedia?
Booking your vacation package on Expedia makes it easier to get more out of your trip from the start. With a wide choice of hotels, you can compare prices, reviews and amenities all in one place, then bundle your hotel with flights which could help you save even more. Flexible booking options on selected stays also make it easier to plan with confidence.

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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.