Search Cheap Flights to
Roxbury

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Roxbury Flights as Low as $101

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

Avelo Airlines
Mon, Apr 27 - Mon, May 11
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$101 Roundtrip, found 17 hours ago
$101
Roundtrip
found 17 hours ago
Select Avelo Airlines flight, departing Mon, Apr 27 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 11, priced at $101 found 17 hours ago
Avelo Airlines
Mon, Apr 13 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$120 Roundtrip, found 6 days ago
$120
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $120 found 6 days ago
Avelo Airlines
Fri, Apr 10 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $121 found 1 day ago
Breeze Airways
Mon, Apr 27 - Mon, May 11
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$127 Roundtrip, found 17 hours ago
$127
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Mon, Apr 27 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 11, priced at $127 found 17 hours ago
Breeze Airways
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$128 Roundtrip, found 1 day ago
$128
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $128 found 1 day ago
Avelo Airlines
Fri, Apr 10 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$130 Roundtrip, found 3 days ago
$130
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $130 found 3 days ago
Breeze Airways
Mon, Apr 27 - Mon, May 11
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$132 Roundtrip, found 17 hours ago
$132
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Mon, Apr 27 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, May 11, priced at $132 found 17 hours ago
Breeze Airways
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$133 Roundtrip, found 1 day ago
$133
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $133 found 1 day ago
Avelo Airlines
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$137 Roundtrip, found 1 day ago
$137
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $137 found 1 day ago
Breeze Airways
Mon, Apr 13 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $138 found 1 day ago
Breeze Airways
Mon, Apr 13 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$143 Roundtrip, found 1 day ago
$143
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $143 found 1 day ago
Breeze Airways
Mon, Apr 13 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$148 Roundtrip, found 1 day ago
$148
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $148 found 1 day ago
Avelo Airlines
Mon, Apr 13 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$149 Roundtrip, found 3 days ago
$149
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $149 found 3 days ago
Breeze Airways
Fri, Apr 10 - Fri, Apr 17
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$150 Roundtrip, found 8 hours ago
$150
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, Apr 17, priced at $150 found 8 hours ago
Breeze Airways
Mon, Apr 13 - Fri, Apr 17
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$154 Roundtrip, found 3 days ago
$154
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Fri, Apr 17, priced at $154 found 3 days ago
Breeze Airways
Fri, Apr 10 - Mon, Apr 13
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$156 Roundtrip, found 3 days ago
$156
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 13, priced at $156 found 3 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 $101, 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 $101 right now, why wait?

Roxbury Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$100

Last Minute Hotel Deals in Roxbury

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! (1,004 reviews)
Room was spotless, staff were friendly. The only thing that I disliked about the experience was the noise coming from other rooms. Also there was no ice dispenser on the 2nd floor so you had to walk all the way back to the lobby or 3rd floor to get a bucket of ice. They could install better shower ...

Reviewed on Feb 20, 2026

Get rates
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 ...
8.6/10 Excellent! (1,005 reviews)
Nice size room

Reviewed on Feb 28, 2026

Get rates
Hyatt House 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! (1,141 reviews)
Checked in, room smelled like smoke just like the whole hotel. Had to change rooms since amenities in the room were missing. Then the next room was missing some other things, called front desk. I was told it would be a few minutes but it never came all night. Expected better from a Marriott but was ...

Reviewed on Mar 2, 2026

Get rates
Courtyard by Marriott Waterbury Downtown
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! (1,085 reviews)
Room and facilty were very clean and in good shape

Reviewed on Feb 28, 2026

Get rates
Hilton Garden Inn Shelton
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

3.5 out of 5
522 Heritage Rd Southbury CT
Book a stay at this spa hotel in Southbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions ...
8.4/10 Very Good! (1,003 reviews)
Was great

Reviewed on Feb 27, 2026

Get rates
Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
64 Knotter Drive Southington CT
Book a stay at this business-friendly hotel in Southington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,002 reviews)
Pool closed. We have stayed here before and the pool wasn’t working then, either.

Reviewed on Feb 24, 2026

Get rates
Holiday Inn Cheshire - Southington by IHG
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 ...
7.8/10 Good! (1,154 reviews)
Check was quick and efficient. I was greeted with curtesy and professionalism. The room was a bit worn down. The furniture was banged up and didn't glide well when opening up the drawers. The lighting was very dim. Maybe install higher wattage bulbs. One of the lamps wasn't working at all. The shower ...

Reviewed on Mar 2, 2026

Get rates
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! (1,005 reviews)
The room was kind of shabby, and not particularly clean. There was NO breakfast until morning #3 when they put out two flavors of instant oatmeal. That's it. Regular coffee, plain tea bags, and empty bottle of coffee mate and instant oatmeal. And they whisked it all away at 9:28 a.m. Staff was ...

Reviewed on Feb 26, 2026

Get rates
Extended Stay America Suites Shelton Fairfield County
See all 675 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.