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Roxbury

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Roxbury Flights as Low as $110

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

Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$110 Roundtrip, found 6 days ago
$110
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $110 found 6 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$113 Roundtrip, found 6 days ago
$113
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $113 found 6 days ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, found 18 hours ago
$114
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $114 found 18 hours ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$115 Roundtrip, found 5 days ago
$115
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $115 found 5 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$116 Roundtrip, found 6 days ago
$116
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $116 found 6 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $118 found 2 days ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$119 Roundtrip, found 18 hours ago
$119
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $119 found 18 hours ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$121 Roundtrip, found 6 days ago
$121
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $121 found 6 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$122 Roundtrip, found 11 hours ago
$122
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $122 found 11 hours ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$123 Roundtrip, found 2 days ago
$123
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $123 found 2 days ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 18 hours ago
$125
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $125 found 18 hours ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$126 Roundtrip, found 11 hours ago
$126
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $126 found 11 hours ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$128 Roundtrip, found 2 hours ago
$128
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Apr 23 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 10, priced at $128 found 2 hours ago
Avelo Airlines
Thu, Jun 11 - Mon, Jun 15
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Thu, Jun 11 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Jun 15, priced at $142 found 3 days ago
Breeze Airways
Fri, Jun 12 - Mon, Jun 15
PBI
Palm Beach Intl.
HVN
Tweed - New Haven Regional
$143 Roundtrip, found 21 hours ago
$143
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Fri, Jun 12 from Palm Beach Intl. to Tweed - New Haven Regional, returning Mon, Jun 15, priced at $143 found 21 hours ago
Breeze Airways
Mon, Jun 15 - Mon, Jun 29
GSP
Greenville-Spartanburg Intl.
HVN
Tweed - New Haven Regional
$604 Roundtrip, found 6 days ago
$604
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Mon, Jun 15 from Greenville-Spartanburg Intl. to Tweed - New Haven Regional, returning Mon, Jun 29, priced at $604 found 6 days ago

Cheap Flights to Roxbury

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

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

Frequently Asked Questions About flights to Roxbury

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

What is the cheapest month to fly to Roxbury?

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 Roxbury are in April, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Roxbury?

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 Roxbury.

What airport is best to fly into Roxbury?

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

How much are flights to Roxbury?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Roxbury on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $110, 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 Roxbury?

The trick to saving a stack of cash on your flight to Roxbury? 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 $110 right now, why wait?

Roxbury Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$110

Last Minute Hotel Deals in Roxbury

Best Western Danbury/Bethel

Best Western Danbury/Bethel

2.5 out of 5
11 Stony Hill Road Bethel CT
Book a stay at this business-friendly hotel in Bethel. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our ...
7.8/10 Good! (1,001 reviews)
Breakfast was very good

Reviewed on Apr 15, 2026

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Best Western Danbury/Bethel
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd Shelton CT
Book a stay at this business-friendly hotel in Shelton. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8/10 Very Good! (1,098 reviews)
satisfied

Reviewed on Apr 16, 2026

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Hilton Garden Inn Shelton
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St Waterbury CT
Stay at this hotel in Waterbury. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (1,178 reviews)
Customer service was extremely poor. Rashheda was fabulous getting me in early, but that’s it. The amenities were terrible.. one pack of coffee, one sugar and one creamer and that’s all you get in your room. Are you kidding me? You turn on the heater or the air conditioner it’s so loud that you have ...

Reviewed on Apr 13, 2026

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Courtyard by Marriott Waterbury Downtown
Hotel Zero Degrees Danbury

Hotel Zero Degrees Danbury

4 out of 5
15 Milestone Road Danbury CT
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and room service. Our guests praise the restaurant and the helpful staff ...
9.2/10 Wonderful! (1,001 reviews)
We had a few personal requests that were met , and exceeded.

Reviewed on Apr 5, 2026

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Hotel Zero Degrees Danbury
Hyatt House Shelton

Hyatt House Shelton

3 out of 5
830 Bridgeport Ave Shelton CT
Book a stay at this business-friendly hotel in Shelton. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
8.4/10 Very Good! (1,000 reviews)
Stay was very good. The room was very clean The hotel is conveniently located. The only request would be to have a mild coffee choice in addition to the bold version that is available.

Reviewed on Apr 12, 2026

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Hyatt House Shelton
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
522 Heritage Road Southbury CT
Book a stay at this boutique hotel in Southbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (1,000 reviews)
Just the bathroom seemed to have had hair in the tub not belonging to us

Reviewed on Apr 12, 2026

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Heritage Hotel, Golf & Conference Center
Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean ...
8/10 Very Good! (1,201 reviews)
Ethan Allen is a respected name in the Danbury area. As soon as you walk into the hotel lobby you can feel the "glamour". But that is as far as it goes. Don't get me wrong the hotel is okay, but it isn't what you expect by what you see when you walk in. The rooms are outdated. I was in a room that ...

Reviewed on Apr 15, 2026

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Ethan Allen Hotel
Extended Stay America Suites Shelton Fairfield County

Extended Stay America Suites Shelton Fairfield County

2.5 out of 5
945 Bridgeport Ave Shelton CT
Book a stay at this business-friendly hotel in Shelton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.4/10 Good! (1,001 reviews)
Grounds need to be kept better. Lots of cigarette butts in parking area. Bathroom door did not close properly. Walls need cleaning where insects were killed and not cleaned. No ice machine for overnight guests. Bed was comfortable and sheets were clean.

Reviewed on Apr 12, 2026

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Extended Stay America Suites Shelton Fairfield County
See all 691 properties in Roxbury
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.