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A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Chester Vacations from $586

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The Latest Chester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Oct 1 - Oct 5

    Latchis Hotel + Flight

    Brattleboro
    4 nights
    2.5 star property
    8.6/10 - Excellent (932 reviews)
    "Great hotel at the best location for seeing this great town without having to drive or park. Easy walk from train station"
    Reviewed July 17, 2026
    Roundtrip • Raleigh (RDU) - Springfield (VSF)
    RDU - ALB • Nonstop ALB - RDU • 1 stop
    $772
    $586
    per traveler
    found 1 day ago
    Latchis Hotel
  • Front of property
    Oct 1 - Oct 5

    Vikings Villages Resort + Flight

    Guilford
    4 nights
    2.0 star property
    10/10 - Exceptional (208 reviews)
    "Beautiful place, extraordinary, Christina was so kind and accommodating."
    Reviewed July 15, 2026
    Roundtrip • Raleigh (RDU) - Springfield (VSF)
    RDU - ALB • Nonstop ALB - RDU • 1 stop
    Save 100% on your flight
    $877
    $645
    per traveler
    found 1 day ago
    Vikings Villages Resort
  • Lobby sitting area
    Oct 4 - Oct 9

    Inn At Mount Snow + Flight

    West Dover
    5 nights
    2.0 star property
    10/10 - Exceptional (75 reviews)
    "Great property with clean rooms, welcoming public areas, amazing views, and quality food & drink choices for breakfast and snacking."
    Reviewed July 3, 2026
    Roundtrip • Dallas (DFW) - Springfield (VSF)
    DFW - EWR • Nonstop LGA - DFW • Nonstop
    $1,101
    $866
    per traveler
    found 1 day ago
    Inn At Mount Snow
  • Property grounds
    Aug 20 - Aug 25

    The Shire Woodstock + Flight

    Woodstock
    5 nights
    3.0 star property
    8.8/10 - Excellent (965 reviews)
    "Great (unique) experience. The staff were incredibly friendly and helpful. Good location with a small town feel in the best possible way. There is some construction going on at the property but it didn’t have any impact. Looking forward to staying there again."
    Reviewed July 11, 2026
    Roundtrip • Dallas (DFW) - Springfield (VSF)
    DFW - RUT • 1 stop RUT - DFW • 1 stop
    $2,128
    $1,730
    per traveler
    found 1 day ago
    The Shire Woodstock
  • Front of property
    Sep 24 - Sep 27

    Stone Hearth Inn and Eatery + Flight

    Chester
    3 nights
    3.0 star property
    9.2/10 - Wonderful (120 reviews)
    "Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
    Reviewed June 14, 2026
    Roundtrip • Dallas (DFW) - Springfield (VSF)
    DFW - BOS • Nonstop BOS - DFW • Nonstop
    $981
    $864
    per traveler
    found 9 hours ago
    Stone Hearth Inn and Eatery

Where to stay in Chester

Find the best Chester areas and neighborhoods for the activities you enjoy most. Learn more about Chester
Learn more about Chester
A forest with autumn foliage in various colors.

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

Garden

Fullerton Inn

Fullerton Inn
2.5 star property
0.2 mi from Chester
8.2 out of 10, Very Good, (441 reviews)
"The building was very quaint and had a historical vibe."
$159 nightly
The price is $173
Jul 26 - Jul 27
Total with taxes and fees
Fullerton Inn
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.
See all properties in Chester

Frequently Asked Questions

How much does a Chester vacation package cost?

You can grab a vacation package to this destination from $586 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.