Search Cheap Flights to
Orwell

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Orwell Flights as Low as $476

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

JetBlue Airways
Thu, Jul 23 - Thu, Jul 30
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$476 Roundtrip, found 2 hours ago
$476
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 30, priced at $476 found 2 hours ago
JetBlue Airways
Thu, Jul 23 - Thu, Jul 30
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$486 Roundtrip, found 2 hours ago
$486
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 30, priced at $486 found 2 hours ago
JetBlue Airways
Tue, Sep 22 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$492 Roundtrip, found 1 hour ago
$492
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $492 found 1 hour ago
American Airlines
Tue, Aug 4 - Wed, Aug 5
DEN
Denver Intl.
RUT
Rutland Southern Vermont Regional
$499 Roundtrip, found 1 day ago
$499
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Aug 4 from Denver Intl. to Rutland Southern Vermont Regional, returning Wed, Aug 5, priced at $499 found 1 day ago
JetBlue Airways
Wed, Sep 23 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$502 Roundtrip, found 2 hours ago
$502
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Sep 23 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $502 found 2 hours ago
JetBlue Airways
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$503 Roundtrip, found 2 hours ago
$503
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $503 found 2 hours ago
JetBlue Airways
Fri, Jul 17 - Thu, Jul 23
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$504 Roundtrip, found 1 hour ago
$504
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Fri, Jul 17 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 23, priced at $504 found 1 hour ago
JetBlue Airways
Thu, Jul 23 - Thu, Jul 30
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$505 Roundtrip, found 2 hours ago
$505
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 30, priced at $505 found 2 hours ago
American Airlines
Sat, Aug 1 - Wed, Aug 5
DEN
Denver Intl.
RUT
Rutland Southern Vermont Regional
$507 Roundtrip, found 1 day ago
$507
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, Aug 1 from Denver Intl. to Rutland Southern Vermont Regional, returning Wed, Aug 5, priced at $507 found 1 day ago
United
Fri, Sep 25 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$508 Roundtrip, found 9 hours ago
$508
Roundtrip
found 9 hours ago
Select United flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $508 found 9 hours ago
JetBlue Airways
Thu, Jul 23 - Thu, Jul 30
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$511 Roundtrip, found 2 hours ago
$511
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Thu, Jul 23 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Thu, Jul 30, priced at $511 found 2 hours ago
United
Tue, Jul 14 - Wed, Jul 22
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$511 Roundtrip, found 2 hours ago
$511
Roundtrip
found 2 hours ago
Select United flight, departing Tue, Jul 14 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Wed, Jul 22, priced at $511 found 2 hours ago
JetBlue Airways
Tue, Sep 22 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 1 hour ago
$513
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Tue, Sep 22 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $513 found 1 hour ago
United
Fri, Sep 25 - Sat, Sep 26
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$513 Roundtrip, found 9 hours ago
$513
Roundtrip
found 9 hours ago
Select United flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $513 found 9 hours ago
Delta
Mon, Sep 21 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$514 Roundtrip, found 3 hours ago
$514
Roundtrip
found 3 hours ago
Select Delta flight, departing Mon, Sep 21 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $514 found 3 hours ago
United
Sat, Sep 12 - Sat, Sep 26
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$578 Roundtrip, found 3 days ago
$578
Roundtrip
found 3 days ago
Select United flight, departing Sat, Sep 12 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Sat, Sep 26, priced at $578 found 3 days 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 July, 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 $476, 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 $476 right now, why wait?

Orwell Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$475

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! (1,000 reviews)
"I love staying at this historic hotel. Ive stayed there twice. It is located near the center of Middlebury so it is near to stores and restaurants. I was visiting family so I didn’t try the onsite restaurant and spa and I didn’t use the a/c since the weather was mild. The beds were very comfortable. ..."

Reviewed on Jun 24, 2026

Get rates
Middlebury Inn
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 ...
8.2/10 Very Good! (1,002 reviews)
"Parking"

Reviewed on Jun 25, 2026

Get rates
Comfort Inn Rutland - Killington
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! (1,001 reviews)
"Great stay for our business trip!"

Reviewed on Jun 23, 2026

Get rates
Hampton Inn Rutland
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! (645 reviews)
"Lovely old world charm. Super friendly staff, very good food and beverage. Excellent stay"

Reviewed on Jun 26, 2026

Get rates
Brandon Inn
Silver Bay YMCA Inn and Conference Center

Silver Bay YMCA Inn and Conference Center

2 out of 5
87 Silver Bay Rd Silver Bay NY
Book a stay at this beach hotel in Silver Bay. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (150 reviews)
"Enjoyed our stay. Will be back. Thanks"

Reviewed on Jun 22, 2026

Get rates
Silver Bay YMCA Inn and Conference Center
Maple Leaf Motel

Maple Leaf Motel

2.5 out of 5
1370 US Route 9 Schroon Lake NY
Book a stay at this golf motel in Schroon Lake. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular ...
8.8/10 Excellent! (592 reviews)
"The place was immaculate and very much tidied up and was so very tranquil and quiet"

Reviewed on Jun 16, 2026

Get rates
Maple Leaf Motel
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! (574 reviews)
"Grest location. Not far from shopping and restaurants."

Reviewed on Jun 25, 2026

Get rates
Courtyard Middlebury
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 (1,000 reviews)
"We ended up staying here unexpectedly while moving across the country. It was a stressful situation with a lot of unknowns, and Paven was incredibly helpful and kind throughout our stay. His willingness to help and positive attitude made a difficult day much easier. We are very grateful for his hospitality ..."

Reviewed on Jun 24, 2026

Get rates
Days Inn by Wyndham Rutland/Killington Area
See all 609 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.