Chester Vacations from $563

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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 $673, price is now $563 per person
$563
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Springfield (VSF)
9.4/10 Exceptional! (37 reviews)
Nice place to stay. in the process of updating, which is needed is some rooms. Would stay again.

Reviewed on Oct 29, 2025

The Shire Woodstock

The Shire Woodstock

3 out of 5
Price was $1,167, price is now $879 per person
$879
per person
Dec 5 - Dec 8
found 21 hours ago
Roundtrip flight included
West Palm Beach (PBI) to Springfield (VSF)
8.8/10 Excellent! (851 reviews)
No balcony but nice river views. Parking just outside the door

Reviewed on Oct 29, 2025

Inn At Mount Snow

Inn At Mount Snow

2 out of 5
Price was $1,022, price is now $808 per person
$808
per person
Jan 5 - Jan 8
found 18 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
10/10 Exceptional! (38 reviews)
From start to finish the staff could not do enough for you and the quality of the inn was amazing

Reviewed on Oct 21, 2025

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Price was $1,264, price is now $1,065 per person
$1,065
per person
Jan 5 - Jan 8
found 18 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Springfield (VSF)
9.2/10 Wonderful! (538 reviews)
Room was very good. Staff was good. Rooms overpriced especially when you add on the $40 resort fee especially since we stayed only one night and did not use resort facilities. Food in main restaurant was just above average considering the overall price of the stay.

Reviewed on Oct 28, 2025

Mountaineer Inn

Mountaineer Inn

2 out of 5
Price was $688, price is now $589 per person
$589
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
West Palm Beach (PBI) to Springfield (VSF)
8.6/10 Excellent! (530 reviews)
Clean room and bathroom, decent mattress. Property being reimagined so no dining available, coffee station and communal microwave located downstairs and not mentioned by on site staff upon arrival, found while checking out the grounds. No fridge or vending machines. Room heater did not seem to work. Not ideal for my stay.

Reviewed on Oct 28, 2025

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Discover the most popular places to visit in Chester

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

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

Chester Hotel Deals

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 Nov 30 to Dec 1
$395 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (544 reviews)
Great staff. Wonderful property, close to the village.

Reviewed on Oct 29, 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
$153 nightly
The price is $168 total per night from Nov 2 to Nov 3
$168 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (867 reviews)
No balcony but nice river views. Parking just outside the door

Reviewed on Oct 29, 2025

The Shire Woodstock
Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103, Cavendish, VT
$136 nightly
The price is $148 total per night from Nov 2 to Nov 3
$148 total
Nov 2 - Nov 3
Total with taxes and fees
8.6/10 Excellent! (909 reviews)
We had a great experience at Resort and the room was clean and very nice.

Reviewed on Oct 29, 2025

Pointe at Castle Hill Resort
See all 2,993 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 $563 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.