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Rupert

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Rupert Flights as Low as $534

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

American Airlines
Fri, Sep 25 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$534 Roundtrip, found 5 days ago
$534
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $534 found 5 days ago
United
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$541 Roundtrip, found 5 days ago
$541
Roundtrip
found 5 days ago
Select United flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $541 found 5 days ago
American Airlines
Fri, Sep 25 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$544 Roundtrip, found 3 days ago
$544
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $544 found 3 days ago
United
Mon, Sep 14 - Tue, Sep 29
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$547 Roundtrip, found 5 days ago
$547
Roundtrip
found 5 days ago
Select United flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $547 found 5 days ago
American Airlines
Mon, Sep 14 - Mon, Sep 28
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$551 Roundtrip, found 5 days ago
$551
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Mon, Sep 28, priced at $551 found 5 days ago
American Airlines
Fri, Sep 25 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$554 Roundtrip, found 3 days ago
$554
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $554 found 3 days ago
United
Fri, Sep 25 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$557 Roundtrip, found 1 day ago
$557
Roundtrip
found 1 day ago
Select United flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $557 found 1 day ago
American Airlines
Mon, Sep 14 - Thu, Oct 1
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$561 Roundtrip, found 5 days ago
$561
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Sep 14 from San Diego Intl. to Rutland Southern Vermont Regional, returning Thu, Oct 1, priced at $561 found 5 days ago
American Airlines
Fri, Sep 25 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$564 Roundtrip, found 3 days ago
$564
Roundtrip
found 3 days ago
Select American Airlines flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $564 found 3 days ago
American Airlines
Fri, Sep 25 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$567 Roundtrip, found 1 day ago
$567
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $567 found 1 day ago
Alaska Airlines
Sun, Sep 13 - Fri, Oct 2
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$570 Roundtrip, found 5 days ago
$570
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Sun, Sep 13 from San Diego Intl. to Rutland Southern Vermont Regional, returning Fri, Oct 2, priced at $570 found 5 days ago
American Airlines
Tue, Sep 15 - Mon, Sep 28
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$572 Roundtrip, found 5 days ago
$572
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Sep 15 from San Diego Intl. to Rutland Southern Vermont Regional, returning Mon, Sep 28, priced at $572 found 5 days ago
American Airlines
Fri, Sep 25 - Wed, Sep 30
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$577 Roundtrip, found 1 day ago
$577
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Sep 25 from San Diego Intl. to Rutland Southern Vermont Regional, returning Wed, Sep 30, priced at $577 found 1 day ago
United
Wed, Sep 16 - Fri, Oct 2
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$577 Roundtrip, found 5 days ago
$577
Roundtrip
found 5 days ago
Select United flight, departing Wed, Sep 16 from San Diego Intl. to Rutland Southern Vermont Regional, returning Fri, Oct 2, priced at $577 found 5 days ago
American Airlines
Wed, Sep 23 - Mon, Oct 5
SAN
San Diego Intl.
RUT
Rutland Southern Vermont Regional
$580 Roundtrip, found 3 days ago
$580
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Sep 23 from San Diego Intl. to Rutland Southern Vermont Regional, returning Mon, Oct 5, priced at $580 found 3 days ago
United
Sat, Sep 26 - Tue, Sep 29
CLD
McClellan-Palomar
RUT
Rutland Southern Vermont Regional
$606 Roundtrip, found 4 days ago
$606
Roundtrip
found 4 days ago
Select United flight, departing Sat, Sep 26 from McClellan-Palomar to Rutland Southern Vermont Regional, returning Tue, Sep 29, priced at $606 found 4 days ago

Cheap Flights to Rupert

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

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

Frequently Asked Questions About flights to Rupert

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

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 Rupert are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Rupert?

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 Rupert.

What airport is best to fly into Rupert?

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

How much are flights to Rupert?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Rupert on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $534, 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 Rupert?

The trick to saving a stack of cash on your flight to Rupert? 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 $534 right now, why wait?

Rupert Flight Information
Destination airport
Rutland Southern Vermont Regional
Destination airport IATA code
RUT
Roundtrip price
$533

Last Minute Hotel Deals in Rupert

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
3567 Main Street Manchester VT
Book a stay at this luxury hotel in Manchester. Enjoy free parking, an outdoor pool, and a full-service spa. Popular attractions Golf Club at Equinox and American ...
7.4/10 Good! (661 reviews)
"First time stay here since we used to own a house in the area. Found the Inn comfortable and the amenities are amazing."

Reviewed on Aug 29, 2026

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The Equinox Golf Resort And Spa
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St. Manchester VT
Book a stay at this golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
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Kimpton Taconic Hotel by IHG
The Palmer House Resort, an Ascend Collection Hotel

The Palmer House Resort, an Ascend Collection Hotel

3 out of 5
5383 Main St Manchester Center VT
Book a stay at this golf hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
8.2/10 Very Good! (999 reviews)
"Nice room and property. With was down."

Reviewed on Aug 29, 2026

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The Palmer House Resort, an Ascend Collection Hotel
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St Manchester Center VT
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! (1,005 reviews)
"Very good breakfast, clean and spacious room, friendly staff."

Reviewed on Aug 27, 2026

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Hampton Inn and Suites Manchester
The Manchester View

The Manchester View

2.5 out of 5
77 High Meadow Way & VT-7A Manchester Center VT
Book a stay at this business-friendly hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and ...
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The Manchester View
Bromley View Inn

Bromley View Inn

3.5 out of 5
522 VT Route 30 Bondville VT
Stay at this B&B in Bondville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Stratton Mountain Resort and Bromley Alpine Slide are located ...
9/10 Wonderful! (472 reviews)
"Very dirty bathroom, shower handle was broken and very hard to use, manager not helpful. Outside stair railing was broken and very."

Reviewed on Aug 29, 2026

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Bromley View Inn
Brittany Motel

Brittany Motel

2 out of 5
1056 Main Street/Historic Route 7A Manchester Center VT
Stay at this motel in Manchester Center. Enjoy free WiFi, free parking, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
9.4/10 Exceptional! (410 reviews)
"Our room had a refrigerator that was very noisy and leaked water on the floor. Overall, it has a nice field to it. There’s a fire pit outside and a snack shack where you can get snacks and things you need for s’mores. The AC was a little loud also, but they have read on the rooms and have done a ..."

Reviewed on Aug 29, 2026

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Brittany Motel
Bentley House Bed and Breakfast

Bentley House Bed and Breakfast

2 out of 5
399 Bentley Ave Poultney VT
Book a stay at this golf B&B in Poultney. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Poultney Public Library and Slate Quarry Park ...
10/10 Exceptional! (11 reviews)
"very clean, very friendly, good breakfast, very nice Victorian style house"

Reviewed on Aug 25, 2026

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Bentley House Bed and Breakfast
See all 1,190 properties in Rupert
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.