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Rupert

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Rupert 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 5 hours ago
$156
Roundtrip
found 5 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 5 hours ago
JetBlue Airways
Sat, May 30 - Tue, Jun 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$163 Roundtrip, found 5 hours ago
$163
Roundtrip
found 5 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 5 hours ago
JetBlue Airways
Mon, May 25 - Tue, Jun 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$167 Roundtrip, found 5 hours ago
$167
Roundtrip
found 5 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 5 hours ago
JetBlue Airways
Sun, May 24 - Tue, Jun 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$167 Roundtrip, found 5 hours ago
$167
Roundtrip
found 5 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 5 hours ago
JetBlue Airways
Fri, May 29 - Tue, Jun 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$178 Roundtrip, found 5 hours ago
$178
Roundtrip
found 5 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 5 hours ago
JetBlue Airways
Sun, May 31 - Mon, Jun 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$183 Roundtrip, found 1 hour ago
$183
Roundtrip
found 1 hour 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 1 hour ago
Cape Air
Tue, May 12 - Tue, Jun 2
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, just found
$184
Roundtrip
just found
Select Cape Air flight, departing Tue, May 12 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Jun 2, priced at $184 just found
Cape Air
Sun, May 31 - Mon, Jun 8
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$184 Roundtrip, found 1 hour ago
$184
Roundtrip
found 1 hour 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 1 hour ago
Cape Air
Sun, May 31 - Sun, May 31
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, found 1 hour ago
$189
Roundtrip
found 1 hour 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 1 hour ago
Cape Air
Tue, May 12 - Tue, Jun 2
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$189 Roundtrip, just found
$189
Roundtrip
just found
Select Cape Air flight, departing Tue, May 12 from Logan Intl. to Rutland Southern Vermont Regional, returning Tue, Jun 2, priced at $189 just found
Cape Air
Sat, May 23 - Thu, May 28
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 2 days ago
$190
Roundtrip
found 2 days 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 2 days ago
JetBlue Airways
Sun, May 31 - Fri, Jun 12
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 5 hours ago
$194
Roundtrip
found 5 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 5 hours ago
JetBlue Airways
Sun, May 31 - Sun, May 31
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 1 hour ago
$194
Roundtrip
found 1 hour 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 1 hour ago
JetBlue Airways
Sat, May 30 - Fri, Jun 12
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 30 from Logan Intl. to Rutland Southern Vermont Regional, returning Fri, Jun 12, 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 day ago
$199
Roundtrip
found 1 day 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 day ago
Cape Air
Sat, May 23 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$200 Roundtrip, just found
$200
Roundtrip
just found
Select Cape Air flight, departing Sat, May 23 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $200 just found

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 May, 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 $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 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 $156 right now, why wait?

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

Last Minute Hotel Deals in Rupert

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. ...
9.4/10 Exceptional! (840 reviews)
We always love this property!!

Reviewed on May 4, 2026

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Kimpton Taconic Hotel by IHG
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A 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! (618 reviews)
We have been coming here for almost twenty years. The property could use a little tlc, but it also has a lot of charm. Pablo at the front desk was the best attendant we have ever had. He really made the experience better. Our AC was not working but within minutes an engineer came up and was able ...

Reviewed on Apr 30, 2026

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The Equinox Golf Resort & Spa
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 ...
8.4/10 Very Good! (934 reviews)
Very satisfied with our stay! Nice hot tub as well as pool

Reviewed on May 4, 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! (1,006 reviews)
Everything was good. We enjoyed our stay.

Reviewed on May 8, 2026

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Hampton Inn and Suites Manchester
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! (352 reviews)
No chocolate for s'mores..otherwise just fine. Only suggestion would be a night light in the bathroom or a dimmer switch.

Reviewed on May 6, 2026

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Brittany Motel
The Inn at Manchester

The Inn at Manchester

3.5 out of 5
3967 Route 7A Manchester VT
Stay at this B&B in Manchester. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions American ...
10/10 Exceptional! (311 reviews)
Staying here was an unexpected delight. It far exceeded my expectations. One of the owners (husband Brian and wife Gaby) were there at all times. Excellent breakfast and a charming bar area with ample selections to accommodate all tastes. It was my first stay and I was here for work, but I will definitely ...

Reviewed on May 8, 2026

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The Inn at Manchester
Aspen At Manchester

Aspen At Manchester

2.5 out of 5
5669 Main Street Manchester Center VT
Stay at this hotel in Manchester Center. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (657 reviews)
Stayed in 2 bedroom lots of space but lacked helpful amenities. No place in bath to put personal items need a shelf or hooks. Small kitchen area had no light at all overhead or lamps. Not enough electrical outlets had to unplug coffee maker to use microwave. One bedroom could use a chair “continental ...

Reviewed on May 8, 2026

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Aspen At Manchester
Weathervane Motel

Weathervane Motel

2 out of 5
2212 Main Street Manchester Center VT
Stay at this motel in Manchester Center. Enjoy free WiFi, daily housekeeping, and satellite TV channels. Our guests praise the helpful staff and the clean rooms ...
6.8/10 (765 reviews)
Every thing was great except the water would shut off at times but then returned

Reviewed on Apr 5, 2026

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Weathervane Motel
See all 1,186 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.