Chester Vacations from $446

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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.
COHO Inn & Motor Lodge

COHO Inn & Motor Lodge

2 out of 5
Price was $612, price is now $446 per person
$446
per person
Dec 27 - Dec 31
found 16 hours ago
Roundtrip flight included
Miami (MIA) to Springfield (VSF)
18.4/10 Exceptional! (43 reviews)
Nice place to stay. in the process of updating, which is needed is some rooms. Would stay again.

Reviewed on Oct 29, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $2,413, price is now $1,774 per person
$1,774
per person
Dec 24 - Dec 29
found 23 hours ago
Roundtrip flight included
Miami (MIA) to Springfield (VSF)
17.2/10 Exceptional! (834 reviews)
Room was very clean and comfortable. Loved having the fireplace. Indoor parking garage was a plus with easy access to our room. We enjoyed dinner and breakfast at the restaurant. The outdoor space was fabulous with many activities.

Reviewed on Nov 14, 2025

Treehouse Home in Ludlow

Treehouse Home in Ludlow

2 out of 5
Save 100% on your flight
Price was $4,715, price is now $3,651 per person
$3,651
per person
Feb 6 - Feb 9
found 5 hours ago
Roundtrip flight included
Augusta (AGS) to Springfield (VSF)
No reviews
The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $806, price is now $628 per person
$628
per person
Feb 6 - Feb 9
found 5 hours ago
Roundtrip flight included
Augusta (AGS) to Springfield (VSF)
17.6/10 Exceptional! (881 reviews)
Clean good service and location

Reviewed on Nov 22, 2025

Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $2,198, price is now $1,734 per person
$1,734
per person
Feb 6 - Feb 9
found 5 hours ago
Roundtrip flight included
Augusta (AGS) to Springfield (VSF)
15.6/10 Exceptional! (28 reviews)
Stayed at this resort for 4 nights while biking in the Vermont area. At check I had reserved a condo without ac but it was in the 90’s and the person checking me in offered to move me to the Inn which had same room set up with Kitchen etc and AC - That was Great!!! After morning riding my husband spent a few hours working while I enjoyed the fitness center as well as indoor and outdoor pools. Very few people here during June.

Reviewed on Jun 26, 2025

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Discover the most popular places to visit in Chester

Bonnie's Bundles Dolls

Enjoy an outing to Bonnie's Bundles Dolls during your stay in Chester. Discover the area's mountain views, or seek out its ski slopes.

Bonnie's Bundles Dolls

DaVallia Art & Accents

Enjoy an outing to DaVallia Art & Accents during your stay in Chester. You can seek out the ski slopes while in the area.

DaVallia Art & Accents

Chester Hotel Deals

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
$369 nightly
The price is $406 total per night from Nov 30 to Dec 1
$406 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (551 reviews)
Clean room, Awesome staff and always a good vibe.

Reviewed on Nov 17, 2025

Woodstock Inn & Resort
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $124 total per night from Nov 30 to Dec 1
$124 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (884 reviews)
Clean good service and location

Reviewed on Nov 22, 2025

The Shire Woodstock
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Fully refundable
$194 nightly
The price is $214 total per night from Dec 1 to Dec 2
$214 total
Dec 1 - Dec 2
Total with taxes and fees
9.2/10 Wonderful! (814 reviews)
Staff was great. Our room was okay… broken blinds and lots of scuffs on walls

Reviewed on Nov 16, 2025

Kimpton Taconic Hotel by IHG
See all 3,020 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

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 $446 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.