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Cheap Flights to Chester

Fall in love at first flight with your vacation to Chester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Chester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Chester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Chester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Chester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the VSF airport.

What is the cheapest month to fly to Chester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Chester are in , but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Chester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find  to choose from for your flight to Chester.

What airport is best to fly into Chester?

When you’re planning your trip to Chester, convenience is the name of the game. Luckily, Chester Hartness State Airport is nearby so you can deplane and get going on checking off everything on your Chester must-do list.

How much are flights to Chester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Chester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as , you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Chester?

The trick to saving a stack of cash on your flight to Chester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as  right now, why wait?

Chester Flight Information
Destination airport
Chester
Destination airport IATA code
VSF

Last Minute Hotel Deals in Chester

The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (821 reviews)
Wonderful place to stay
"We love Woodstock and this was out first time staying here at The Shire. The staff was very friendly, and the room was fun and clean, and oh what a view!"

Reviewed on Sep 14, 2025

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The Shire Woodstock
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (533 reviews)
Old world charm
"What a wonderful inn. Same class as The Greenbrier and The Homestead. Old world charm."

Reviewed on Sep 12, 2025

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Woodstock Inn & Resort
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the property condition in our ...
7.2/10 Good! (529 reviews)
"The hotel prominently promotes walking trails in and near on their property. While they provide maps no staff could explain how to access. The maps were very confusing. We set out and could not find a trail head. We finally used Google Maps and found that the nearest access was a few blocks away ..."

Reviewed on Sep 14, 2025

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The Equinox Golf Resort & Spa
Jackson Gore Village

Jackson Gore Village

3 out of 5
111 Jackson Gore Road, Ludlow, VT
Stay at this 3-star spa hotel in Ludlow. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (762 reviews)
"The hotel was peaceful and clean, perfect for the weekend getaway."

Reviewed on Sep 15, 2025

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Jackson Gore Village
Days Inn by Wyndham Keene NH

Days Inn by Wyndham Keene NH

2 out of 5
3 Ash Brook Road, Keene, NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7/10 Good! (1,004 reviews)
"A group of us come here every year and we never hesitate to come back. Not the Ritz, but perfectly fine and very reasonably priced to have access to a pretty nice part of NH."

Reviewed on Sep 20, 2025

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Days Inn by Wyndham Keene NH
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the ...
9.6/10 Exceptional! (1,005 reviews)
"I want to go back to this Hotel again in the future."

Reviewed on Sep 14, 2025

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Hampton Inn and Suites Manchester
Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel

2.5 out of 5
175 Key Rd, Keene, NH
Book a stay at this business-friendly hotel in Keene. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8.4/10 Very Good! (898 reviews)
Not A 4 Star Hotel But 4 Stars For Value
"One of the more affordable options in Keene, it was much better than we expected"

Reviewed on Sep 7, 2025

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Keene Elm City Hotel, an Ascend Collection Hotel
Hampton Inn Brattleboro

Hampton Inn Brattleboro

2.5 out of 5
1378 Putney Road, Brattleboro, VT
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the breakfast and the ...
8/10 Very Good! (884 reviews)
AOK
"Staff was very friendly and professional. Bed was very comfortable! Breakfast was good!"

Reviewed on Sep 16, 2025

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Hampton Inn Brattleboro
See all 2,976 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.