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Charlestown

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Charlestown Flights as Low as $163

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Sat, May 30 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$163 Roundtrip, found 6 hours ago
$163
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $163 found 6 hours ago
JetBlue Airways
Mon, May 4 - Wed, May 20
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$174 Roundtrip, found 7 hours ago
$174
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 20, priced at $174 found 7 hours ago
JetBlue Airways
Wed, May 27 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$178 Roundtrip, found 6 hours ago
$178
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Wed, May 27 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $178 found 6 hours ago
Cape Air
Sat, May 30 - Mon, Jun 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 6 hours ago
$180
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 8, priced at $180 found 6 hours ago
JetBlue Airways
Sat, Apr 25 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 6 hours ago
$184
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Sat, Apr 25 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $184 found 6 hours ago
Cape Air
Thu, May 28 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 2 hours ago
$184
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $184 found 2 hours ago
Cape Air
Sat, May 30 - Wed, Jun 10
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$186 Roundtrip, found 6 hours ago
$186
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 10, priced at $186 found 6 hours ago
JetBlue Airways
Sat, Apr 18 - Mon, Apr 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$188 Roundtrip, found 11 hours ago
$188
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Sat, Apr 18 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 27, priced at $188 found 11 hours ago
JetBlue Airways
Sat, Apr 25 - Thu, Apr 30
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 6 hours ago
$189
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Sat, Apr 25 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Apr 30, priced at $189 found 6 hours ago
Cape Air
Sat, May 30 - Sun, Jun 7
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 6 hours ago
$190
Roundtrip
found 6 hours ago
Select Cape Air flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 7, priced at $190 found 6 hours ago
JetBlue Airways
Sat, Apr 18 - Mon, Apr 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$193 Roundtrip, found 11 hours ago
$193
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Sat, Apr 18 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 27, priced at $193 found 11 hours ago
Cape Air
Mon, Jun 1 - Thu, Jun 11
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 2 hours ago
$194
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Mon, Jun 1 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, Jun 11, priced at $194 found 2 hours ago
JetBlue Airways
Sat, May 30 - Wed, Jun 10
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 6 hours ago
$196
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Sat, May 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, Jun 10, priced at $196 found 6 hours ago
Cape Air
Sat, May 23 - Sun, Jun 7
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 2 days ago
$196
Roundtrip
found 2 days ago
Select Cape Air flight, departing Sat, May 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, Jun 7, priced at $196 found 2 days ago
JetBlue Airways
Sun, Apr 19 - Mon, Apr 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$199 Roundtrip, found 10 hours ago
$199
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Sun, Apr 19 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 27, priced at $199 found 10 hours ago
JetBlue Airways
Tue, Aug 25 - Tue, Sep 1
DEN
Denver Intl.
RUT
Rutland Southern Vermont Regional
$438 Roundtrip, found 11 hours ago
$438
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Aug 25 from Denver Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 1, priced at $438 found 11 hours ago

Cheap Flights to Charlestown

Fall in love at first flight with your vacation to Charlestown 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 Charlestown on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Charlestown

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Charlestown 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 Charlestown?

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 Charlestown are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Charlestown?

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 Charlestown.

What airport is best to fly into Charlestown?

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

How much are flights to Charlestown?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Charlestown on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $163, 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 Charlestown?

The trick to saving a stack of cash on your flight to Charlestown? 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 $163 right now, why wait?

Charlestown Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$163

Last Minute Hotel Deals in Charlestown

Pointe at Castle Hill Resort

Pointe at Castle Hill Resort

3.5 out of 5
2940 State Route 103 Cavendish VT
Book a stay at this spa hotel in Cavendish. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,002 reviews)
Super kind staff members. Our family arrived early, and they were able to find a room for us within an hour. Pool is clean as well!

Reviewed on Apr 15, 2026

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Pointe at Castle Hill Resort
Hideaway Inn Mt.Sunapee

Hideaway Inn Mt.Sunapee

2 out of 5
1403 New Hampshire Rte 103 Newbury NH
Stay at this hotel in Newbury. Enjoy free WiFi, free parking, and a fireplace in the lobby. Popular attractions John Hay National Wildlife Refuge and Mount Sunapee ...
8.8/10 Excellent! (159 reviews)
This hotel was recently updated and it is fabulous!It had an active room for every age and a beautiful indoor pool equipped even for handicapped guest.Outside a great firepit with outdoor trials to small sledding hill and further down to a wonderful sandy lake beach. Great place anytime of year from ...

Reviewed on Apr 13, 2026

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Hideaway Inn Mt.Sunapee
Holiday Inn Club Vacations Mount Ascutney Resort by IHG

Holiday Inn Club Vacations Mount Ascutney Resort by IHG

3 out of 5
485 Hotel Road Brownsville VT
Stay at this resort in Brownsville. Enjoy an outdoor pool, a business center, and a fireplace in the lobby. Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (825 reviews)
Staff were super friendly. Miles was great to deal with. Amazing gentleman and very friendly and helpful. Others were also equally helpful. Loved it!

Reviewed on Apr 9, 2026

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Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Best Western Plus Keene Hotel

Best Western Plus Keene Hotel

3 out of 5
401 Winchester St 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! (1,001 reviews)
The breakfast nook was excellent ! Many choices laid out neat and easy.

Reviewed on Apr 16, 2026

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Best Western Plus Keene Hotel
Best Western Springfield Hotel

Best Western Springfield Hotel

2.5 out of 5
818 Charlestown Rd Springfield VT
Stay at this hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (849 reviews)
Location and amenities were great and so was breakfast

Reviewed on Apr 10, 2026

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Best Western Springfield Hotel
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 ...
8.6/10 Excellent! (1,001 reviews)
The room was very clean and the staff was very nice and there was plenty of parking. It was also within walkable distance of a movie theater and several fast food restaurants. Perf

Reviewed on Apr 12, 2026

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Keene Elm City Hotel, an Ascend Collection Hotel
The Putney Inn

The Putney Inn

2.5 out of 5
57 Putney Landing Rd Putney VT
Book a stay at this business-friendly motel in Putney. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,002 reviews)
It's clear the owners are refurbishing this motel right off I-91 in Putney, VT. The bathrooms are freshly tiles, wooden floors replace wall to wall carpet, new lighting and thermo pane sliding doors. If you need a bed on a long drive, support these folks. Putney Food Coop is just up the road for ...

Reviewed on Apr 15, 2026

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The Putney Inn
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! (1,000 reviews)
This property was definitely on the older side and could use some renos. All of the towels in my room were stained, and the kleenex boxes left empty. I don't think one single staff member greeted me during the 3 nights I stayed there. They just sat behind the desk or walked about but never said hello ...

Reviewed on Apr 15, 2026

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Days Inn by Wyndham Keene NH
See all 1,508 properties in Charlestown
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.