Chester Vacations from $720
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The Latest Chester Vacation Packages
- Stone Hearth Inn and Eatery
Oct 9 - Oct 11Stone Hearth Inn and Eatery + Flight
Chester2 nights3.0 star property9.2/10 - Wonderful (121 reviews)Roundtrip • Houston (HOU) - Springfield (VSF)IAH - ALB • 1 stop ALB - IAH • 1 stop$845$720found 13 hours agoper traveler - The Shire Woodstock
Sep 8 - Sep 14The Shire Woodstock + Flight
Woodstock6 nights3.0 star property8.8/10 - Excellent (969 reviews)"It would be great to have a coffee maker in the room"Reviewed July 31, 2026Roundtrip • Chicago (CHI) - Springfield (VSF)ORD - RUT • 1 stop RUT - ORD • 1 stop$2,045$1,580found 1 day agoper traveler - Vikings Villages Resort
Oct 29 - Nov 2Vikings Villages Resort + Flight
Guilford4 nights2.0 star property10/10 - Exceptional (222 reviews)"Super fun environment. Wish we had more time to stay there. In the middle of nowhere yet still close to food places and other activities."Reviewed August 5, 2026Roundtrip • Houston (HOU) - Springfield (VSF)IAH - ALB • 1 stop ALB - HOU • 1 stop$1,046$851found 11 hours agoper traveler - Jackson Gore Village, A Vail Resorts Property
Sep 8 - Sep 14Jackson Gore Village, A Vail Resorts Property + Flight
Jackson Gore Base Area6 nights3.0 star property8.6/10 - Excellent (878 reviews)"Beautiful resort. I love it!"Reviewed August 4, 2026Roundtrip • Chicago (CHI) - Springfield (VSF)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,171$983found 1 day agoper traveler - Solitude Village at Okemo by Vail Resorts
Sep 8 - Sep 14Solitude Village at Okemo by Vail Resorts + Flight
Clock Tower Base Area6 nights4.0 star property7.8/10 - Good (35 reviews)Roundtrip • Chicago (CHI) - Springfield (VSF)ORD - RUT • 1 stop RUT - ORD • 1 stop$1,278$1,091found 1 day agoper traveler
Where to stay in Chester
Chester Depot
If you're spending some time in Chester Depot, DaVallia Art & Accents and Bonnie's Bundles Dolls are top sights worth seeing.
Chester Hotel Deals
"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 they said it would parking was good. We had a great time nice people to deal with."
"Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
"We liked our welcome when we arrived approximately 3:30 pm. The front desk person offered us an upgrade to have a jacuzzi, but we refused. We only wanted the room we booked with a couch. The room was very spacious and on the first floor, which is important to us, even though we didn’t request it. The front desk person gave us a list of area restaurants. When asked she told us about the Sumer House on the third page. We looked all the restaurants over and decided to take her recommendation. Our...
The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic Mountain
"The house was beautiful and very nice. It was a self check in and I did speak to one person as I was checking in who was also very nice. We stayed in the hotel part and the beds were very small. Plus side it was a quiet area and we were not disturbed. Air conditioning work great. Downside, we never saw another staff member accept when we checked in. No one was around anywhere. There was a dining room but it was closed. When we checked out it was a self checkout and I had no one to give...
"I arrived to find out the inn was closed for a privare event. Had to find some other place to stay at 11pm. Im still waiting for my refund."
Frequently Asked Questions
How much does a Chester vacation package cost?
You can grab a vacation package to this destination from $720 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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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.
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.
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.