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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?

Last Minute Hotel Deals in Chester

Fullerton Inn
Fullerton Inn
2.5 out of 5
40 The Common, Chester, VT
The price is $141 per night from May 9 to May 10
$141
includes taxes & fees
May 9 - May 10
Stay at this inn in Chester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (347 reviews)
"Excellent service to help resolve reservation mix up. Small but serviceable room. Very limited breakfast. On premises restaurant was excellent for dinner"

Reviewed on Mar 22, 2025

Fullerton Inn
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $384 per night from May 26 to May 27
$384
includes taxes & fees
May 26 - May 27
Book a stay at this 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! (515 reviews)
Beautiful Inn
"Gorgeous inn, staff was wonderful, beautiful lobby, library and other sitting rooms. Walking distance to shops and restaurants. Also a pet friendly inn."

Reviewed on Apr 29, 2025

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
The price is $176 per night from May 11 to May 12
$176
includes taxes & fees
May 11 - May 12
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! (471 reviews)
"We a been coming to the Equinox multiple times a year for over 20 years but had not been here in over a year because the last time I was there it was not a pleasant experience. I am happy to say things are back to being very enjoyable again and we will be back soon!"

Reviewed on Apr 25, 2025

The Equinox Golf Resort & Spa
Best Western Plus Keene Hotel
Best Western Plus Keene Hotel
3 out of 5
401 Winchester St, Keene, NH
The price is $143 per night from May 12 to May 13
$143
includes taxes & fees
May 12 - May 13
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 ...
8.2/10 Very Good! (1,008 reviews)
"Good place to stay"

Reviewed on May 5, 2025

Best Western Plus Keene Hotel
Colonial Motel And Spa
Colonial Motel And Spa
3 out of 5
889 Putney Rd, Brattleboro, VT
The price is $120 per night from May 11 to May 12
$120
includes taxes & fees
May 11 - May 12
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 (1,000 reviews)
"A little steep on nightly accommodation pricing considering the shape things are in which is "in disrepair". Staff was excellent, room okay. I would consider staying again but only if you are negotiable on the nightly rate."

Reviewed on Apr 20, 2025

Colonial Motel And Spa
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
The price is $132 per night from May 27 to May 28
$132
includes taxes & fees
May 27 - May 28
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! (738 reviews)
Lovely stay in the village
"Woodstock is charming, I love staying at Shire. Walk to town, plenty to do, tranquil setting."

Reviewed on May 4, 2025

The Shire Woodstock
Kimpton Taconic Hotel by IHG
Kimpton Taconic Hotel by IHG
4 out of 5
3835 Main St., Manchester, VT
The price is $184 per night from May 14 to May 15
$184
includes taxes & fees
May 14 - May 15
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property ...
9.2/10 Wonderful! (763 reviews)
"Really cool property!"

Reviewed on May 1, 2025

Kimpton Taconic Hotel by IHG
506 On the River Inn
506 On the River Inn
4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is $213 per night from May 11 to May 12
$213
includes taxes & fees
May 11 - May 12
Stay at this 4-star family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (996 reviews)
Highly recommend for a relaxing getaway
"What a lovely quiet place - great location, spotless well furnished rooms, comfy beds. Beautiful pool/sauna/hot tub area with nice outdoor vista. We didn't eat onsite but had cocktails at the bar, which were expertly made and delicious. And of course in the beautiful surroundings of Woodstock!"

Reviewed on May 5, 2025

506 On the River Inn
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.