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Orwell

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Orwell Flights as Low as $156

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

JetBlue Airways
Tue, May 26 - Tue, Jun 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$156 Roundtrip, found 6 hours ago
$156
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Tue, May 26 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Jun 16, priced at $156 found 6 hours ago
JetBlue Airways
Sat, May 30 - Tue, Jun 16
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 Tue, Jun 16, priced at $163 found 6 hours ago
JetBlue Airways
Mon, May 25 - Tue, Jun 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$167 Roundtrip, found 6 hours ago
$167
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Mon, May 25 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Jun 16, priced at $167 found 6 hours ago
JetBlue Airways
Sun, May 24 - Tue, Jun 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$167 Roundtrip, found 6 hours ago
$167
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Sun, May 24 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Jun 16, priced at $167 found 6 hours ago
JetBlue Airways
Fri, May 29 - Tue, Jun 16
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 Fri, May 29 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Jun 16, priced at $178 found 6 hours ago
JetBlue Airways
Sun, May 31 - Mon, Jun 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, found 3 hours ago
$183
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 8, priced at $183 found 3 hours ago
Cape Air
Tue, May 12 - Tue, Jun 2
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 Tue, May 12 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Jun 2, priced at $184 found 2 hours ago
Cape Air
Sun, May 31 - Mon, Jun 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 3 hours ago
$184
Roundtrip
found 3 hours ago
Select Cape Air flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 8, priced at $184 found 3 hours ago
Cape Air
Sun, May 31 - Sun, May 31
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 2 hours ago
$189
Roundtrip
found 2 hours ago
Select Cape Air flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, May 31, priced at $189 found 2 hours ago
JetBlue Airways
Sun, May 24 - Thu, May 28
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 1 hour ago
$189
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sun, May 24 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, May 28, priced at $189 found 1 hour ago
Cape Air
Sat, May 23 - Thu, May 28
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 1 hour ago
$190
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Sat, May 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, May 28, priced at $190 found 1 hour ago
JetBlue Airways
Sun, May 31 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 6 hours ago
$194
Roundtrip
found 6 hours ago
Select JetBlue Airways flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, priced at $194 found 6 hours ago
JetBlue Airways
Sun, May 31 - Sun, May 31
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 2 hours ago
$194
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Sun, May 31 from Logan Intl. to Rutland Southern Vermont Regional, returning Sun, May 31, priced at $194 found 2 hours ago
JetBlue Airways
Sat, May 23 - Thu, May 28
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 1 hour ago
$196
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Sat, May 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, May 28, priced at $196 found 1 hour ago
Cape Air
Sun, May 24 - Thu, May 28
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$199 Roundtrip, found 1 hour ago
$199
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Sun, May 24 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, May 28, priced at $199 found 1 hour ago
Cape Air
Sat, May 23 - Thu, May 28
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$200 Roundtrip, found 1 hour ago
$200
Roundtrip
found 1 hour ago
Select Cape Air flight, departing Sat, May 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Thu, May 28, priced at $200 found 1 hour ago

Cheap Flights to Orwell

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

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

Frequently Asked Questions About flights to Orwell

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

What is the cheapest month to fly to Orwell?

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

How many airlines fly to Orwell?

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 Orwell.

What airport is best to fly into Orwell?

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

How much are flights to Orwell?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Orwell on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $156, 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 Orwell?

The trick to saving a stack of cash on your flight to Orwell? 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 $156 right now, why wait?

Orwell Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$156

Last Minute Hotel Deals in Orwell

Middlebury Inn

Middlebury Inn

3 out of 5
14 Court Square Middlebury VT
Book a stay at this spa hotel in Middlebury. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (1,007 reviews)
We loved the central location but there was a small bathroom with limited hooks and shelving for toiletries. Our room was a second floor walk up but the is a staff operated lift if needed. There is no kettle or coffee machine in the room.

Reviewed on May 4, 2026

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Middlebury Inn
Lake Bomoseen Lodge

Lake Bomoseen Lodge

3.5 out of 5
2551 Vermont 30N Bomoseen VT
Book a stay at this beach lodge in Bomoseen. Enjoy free parking, an outdoor pool, and a private beach. Our guests praise the restaurant and the helpful staff ...
9.4/10 Exceptional! (923 reviews)
The room was very clean and the beds comfortable with extra pillows and blankets. The staff friendly and the stay easy. All the amenities one needs. Breakfast coffee and small food options in lobby were a good touch. I enjoyed the taproom for dinner too.

Reviewed on May 8, 2026

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Lake Bomoseen Lodge
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7 Rutland VT
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.6/10 (1,007 reviews)
Room was found with food in frig and water bottle found on the floor with hair on floor in bathroom. Pool was awesome! Breakfast was ok(except ran out of syrup (with no more to fill) sausage was not cooked! Staff fighting loudly at desk. The smell of dope reaked through the halls.. staff was friendly ...

Reviewed on May 4, 2026

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Days Inn by Wyndham Rutland/Killington Area
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (1,005 reviews)
Quick check in clean room good for a one night need easy breakfast options . Ice machine did not work.

Reviewed on May 5, 2026

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Comfort Inn Rutland - Killington
Brandon Inn

Brandon Inn

3 out of 5
20 Park Street Brandon VT
Stay at this hotel in Brandon. 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! (626 reviews)
We were put on the 4th floor and my husband is in his 80’s and I have been sryggling with a Lyme disease therefore it wasn’t as easy to go up and down 4 flights of stairs. They had an old fashioned elevator but no one was there when we were coming and going. They had a claw tub was unique but difficult. ...

Reviewed on May 9, 2026

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Brandon Inn
Hampton Inn Rutland

Hampton Inn Rutland

2.5 out of 5
47 Farrell Rd Rutland VT
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,004 reviews)
Dry nice stay

Reviewed on May 9, 2026

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Hampton Inn Rutland
Courtyard Middlebury

Courtyard Middlebury

3 out of 5
309 Court Street Middlebury VT
Book a stay at this business-friendly hotel in Middlebury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8.8/10 Excellent! (565 reviews)
We were in Middlebury to visit the college. The location of the hotel was convenient. Staff are helpful and friendly. Breakfast is an extra cost, and not very good. Would return

Reviewed on Apr 18, 2026

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Courtyard Middlebury
Cortina Inn

Cortina Inn

3 out of 5
476 Holiday Drive Rutland VT
Book a stay at this business-friendly hotel in Rutland. Enjoy free WiFi, free parking, and a free airport shuttle. Popular attractions Green Mountain Shopping ...
6.4/10 (714 reviews)
Hotel is under going renovations. Staff was very helpful. Room was fine, clean and quiet.

Reviewed on May 2, 2026

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Cortina Inn
See all 586 properties in Orwell
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.