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Chester

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Chester Flights as Low as $465

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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.

Just the right flight

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.

Frequently Asked Questions About flights to Chester

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 September, 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 16 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 $465, 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 $465 right now, why wait?

Can I fly to Chester right now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to  right now?” When it’s time to book your flight, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.

Chester Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$443

Last Minute Hotel Deals in Chester

The Covered Bridge Inn
The Covered Bridge Inn
2.5 out of 5
1043 Putney Road, Brattleboro, VT
The price is $85 per night from May 19 to May 20
$85
per night
May 19 - May 20
Book a stay at this business-friendly hotel in Brattleboro. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,000 reviews)
"Accomodations were clean and room was nice. Property wedged between a McDonalds and a Wendy's. Good for a quick overnight"

Reviewed on May 11, 2024

The Covered Bridge Inn
Stone Hearth Inn and Eatery
Stone Hearth Inn and Eatery
2 out of 5
698 VT-11, Chester, VT
The price is $233 per night from May 19 to May 20
$233
per night
May 19 - May 20
Stay at this B&B in Chester. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Bonnie's Bundles Dolls and DaVallia Art & Accents are located ...
9/10 Wonderful! (48 reviews)
After the eclipse
"Vicky and her family are wonderful hosts. We stayed on the last day of their season and received as welcoming a reception as you might expect at the height of the season. Stonehearth Inn is a labor of love and it shows."

Reviewed on Apr 10, 2024

Stone Hearth Inn and Eatery
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $299 per night from May 19 to May 20
$299
per night
May 19 - May 20
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Popular attractions Woodstock Town Hall Theatre and ...
9.2/10 Wonderful! (441 reviews)
"All staff were friendly and helpful. The room was spacious and comfortable. We took advantage of the spa on premises, and though everything was pricier than were used to paying, the spa and 3 night stay - very enjoyable."

Reviewed on May 3, 2024

Woodstock Inn & Resort
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
The price is $89 per night from May 19 to May 20
$89
per night
May 19 - May 20
Stay at this 3-star spa motel in Brattleboro. Enjoy free WiFi, free parking, and 2 indoor pools. Our guests praise the helpful staff and the clean rooms in our ...
6.8/10 (1,001 reviews)
"Nic big comfortable rooms"

Reviewed on May 15, 2024

Colonial Motel And Spa
Hampton Inn and Suites Manchester
Hampton Inn and Suites Manchester
2.5 out of 5
4519 Main St, Manchester Center, VT
The price is $161 per night from May 23 to May 24
$161
per night
May 23 - May 24
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! (1,000 reviews)
"Great stay! Friendly and helpful staff. Clean rooms. The added bonus was the electric vehicle chargers on site."

Reviewed on May 13, 2024

Hampton Inn and Suites Manchester
The Equinox Golf Resort & Spa
The Equinox Golf Resort & Spa
4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
The price is $146 per night from Jun 3 to Jun 4
$146
per night
Jun 3 - Jun 4
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, a full-service spa, and 4 restaurants. Our guests praise the helpful staff and the property ...
7.2/10 Good! (351 reviews)
"No thanks"

Reviewed on Apr 8, 2024

The Equinox Golf Resort & Spa
Pointe at Castle Hill Resort
Pointe at Castle Hill Resort
3.5 out of 5
2940 State Route 103, Cavendish, VT
The price is $169 per night from May 19 to May 20
$169
per night
May 19 - May 20
Stay at this 3.5-star spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (727 reviews)
"Pet friendly"

Reviewed on May 15, 2024

Pointe at Castle Hill Resort
Kimpton Taconic Hotel, an IHG Hotel
Kimpton Taconic Hotel, an IHG Hotel
4 out of 5
3835 Main St., Manchester, VT
The price is $188 per night from May 27 to May 28
$188
per night
May 27 - May 28
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the clean rooms and the property ...
9.4/10 Exceptional! (680 reviews)
Beautiful Hotel in a Beautiful Little Town
"From the moment you walk in you are greeted by a friendly staff who make it clear that you having a good time is their primary purpose. I just had to ask and a microwave was provided for our room. The rooms are bright and comfortable, and each closet comes with a walking stick for hiking on the fabulous ..."

Reviewed on May 13, 2024

Kimpton Taconic Hotel, an IHG Hotel
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.