Chester Vacations from $326

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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 $426, price is now $326 per person
$326
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
8.4/10 Very Good! (822 reviews)
Great place. Historic—not for people who want fancy but clean with comfortable beds, very walkable to everything. Loved it!

Reviewed on Nov 26, 2025

Jackson Gore Village

Jackson Gore Village

3 out of 5
Jackson Gore Base Area
Save 100% on your flight
Price was $1,856, price is now $1,444 per person
$1,444
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Wilmington (ILM) to Springfield (VSF)
8.6/10 Excellent! (834 reviews)
Very clean, everyone was so nice. Food at restaurant is a little pricey but was very good.

Reviewed on Nov 30, 2025

Solitude Village at Okemo

Solitude Village at Okemo

4 out of 5
Clock Tower Base Area
Save 100% on your flight
Price was $13,037, price is now $10,404 per person
$10,404
per person
Jan 29 - Feb 3
found 1 day ago
Roundtrip flight included
Wilmington (ILM) to Springfield (VSF)
8/10 Very Good! (31 reviews)
Our room was really nice! It was the bathrooms the reason why we didn't rate this place better. We did let the front desk know Both bathrooms had mold in the showers. One person in our party is extremely allergic to mold. I myself could clean the mold off, which I did partially. The dishwasher had dirty dishes in also.

Reviewed on Oct 8, 2025

Econo Lodge Brattleboro

Econo Lodge Brattleboro

2 out of 5
Price was $543, price is now $440 per person
$440
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) to Springfield (VSF)
5.4/10 (591 reviews)
Lobby small but nice, staff good. First room was not made up. 2nd room smelled bad, musty. 3rd room tolerable. REALLY needs an upgrade to the walls, doors, etc. drywall chipped, door not fitting well (cracks), curtain barely covers window. Sinks, toilet and shower were newer, nice. Bed was fine, comfy, looked clean. Nice to have Burger King and Circle K across street. All in all, what do you expect for $60. I would probably not stay here again, but it was OK for 1 night.

Reviewed on Nov 22, 2025

Mount Snow Grand Summit Resort

Mount Snow Grand Summit Resort

3 out of 5
Save 100% on your flight
Price was $1,762, price is now $1,454 per person
$1,454
per person
Jan 29 - Feb 2
found 1 day ago
Roundtrip non-stop flight included
Wilmington (ILM) to Springfield (VSF)
8.8/10 Excellent! (242 reviews)
Amazing 2 big hot tubes and warm swim pool on the open air !!! A lot of restaurants around and Beautiful nature! But chairlifts was closed- so check availability

Reviewed on Oct 18, 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
$379 nightly
The price is $417 total per night from Dec 16 to Dec 17
$417 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (552 reviews)
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town

Reviewed on Nov 26, 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
$171 nightly
The price is $188 total per night from Dec 17 to Dec 18
$188 total
Dec 17 - Dec 18
Total with taxes and fees
8.6/10 Excellent! (885 reviews)
Wonderful place to stay!

Reviewed on Dec 3, 2025

The Shire Woodstock
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A Manchester VT
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $236 total per night from Dec 11 to Dec 12
$236 total
Dec 11 - Dec 12
Total with taxes and fees
7.4/10 Good! (572 reviews)
Courteous staff Clean room

Reviewed on Nov 22, 2025

The Equinox Golf Resort & Spa
See all 3,050 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 $326 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.