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 $112

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

Avelo Airlines
Fri, Apr 10 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$112 Roundtrip, found 4 days ago
$112
Roundtrip
found 4 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 $112 found 4 days ago
Avelo Airlines
Fri, Apr 10 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$122 Roundtrip, found 20 hours ago
$122
Roundtrip
found 20 hours ago
Select Avelo Airlines flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Apr 22, priced at $122 found 20 hours ago
Avelo Airlines
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$138 Roundtrip, found 19 hours ago
$138
Roundtrip
found 19 hours ago
Select Avelo Airlines flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $138 found 19 hours ago
Avelo Airlines
Mon, Apr 13 - Wed, Apr 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$141 Roundtrip, found 4 days ago
$141
Roundtrip
found 4 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 $141 found 4 days ago
Breeze Airways
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$145 Roundtrip, found 19 hours ago
$145
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $145 found 19 hours ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$146 Roundtrip, just found
$146
Roundtrip
just found
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $146 just found
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $147 found 4 days ago
Breeze Airways
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$150 Roundtrip, found 19 hours ago
$150
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $150 found 19 hours ago
Avelo Airlines
Mon, Apr 13 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$151 Roundtrip, found 2 hours ago
$151
Roundtrip
found 2 hours ago
Select Avelo Airlines flight, departing Mon, Apr 13 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $151 found 2 hours ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$152 Roundtrip, found 4 days ago
$152
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $152 found 4 days ago
Breeze Airways
Thu, Apr 23 - Sun, May 10
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$153 Roundtrip, found 6 days ago
$153
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 $153 found 6 days ago
Breeze Airways
Fri, Apr 10 - Mon, Apr 20
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$155 Roundtrip, found 19 hours ago
$155
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Fri, Apr 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Apr 20, priced at $155 found 19 hours ago
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$157 Roundtrip, just found
$157
Roundtrip
just found
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $157 just found
Breeze Airways
Thu, May 14 - Sun, May 17
ORF
Norfolk Intl.
HVN
Tweed - New Haven Regional
$158 Roundtrip, found 4 days ago
$158
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, May 14 from Norfolk Intl. to Tweed - New Haven Regional, returning Sun, May 17, priced at $158 found 4 days ago
Avelo Airlines
Thu, Mar 26 - Sun, Mar 29
DFW
Dallas-Fort Worth Intl.
HVN
Tweed - New Haven Regional
$196 Roundtrip, found 3 days ago
$196
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Thu, Mar 26 from Dallas-Fort Worth Intl. to Tweed - New Haven Regional, returning Sun, Mar 29, priced at $196 found 3 days ago
Avelo Airlines
Fri, May 1 - Sun, May 3
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$220 Roundtrip, found 5 days ago
$220
Roundtrip
found 5 days ago
Select Avelo Airlines flight, departing Fri, May 1 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, May 3, priced at $220 found 5 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 $112, 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 $112 right now, why wait?

Roxbury Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$111

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! (1,005 reviews)
The hard floors in my hotel room made my feet filthy. There was some strange color stains on the blankets that was there when I first arrived at the room.

Reviewed on Mar 23, 2026

Get rates
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! (1,094 reviews)
good I loved my stay

Reviewed on Mar 20, 2026

Get rates
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! (1,158 reviews)
Internet was very slow and called desk to fix my tv never showed up. Won’t stay again

Reviewed on Mar 22, 2026

Get rates
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! (1,005 reviews)
Room insulation was extremely poor for a remolded hotel You could hear everything from floor to floor and room to room Even the sweeking beds when they are F…ing It was disrespectful discussing and poorly designed If you have children in the room what do you say the noise was ???? Do not book if ...

Reviewed on Mar 21, 2026

Get rates
Hotel Zero Degrees Danbury
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 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)
Breakfast was a BIG disappointment…cold and bland …the room was good and staff very nice but you really shouldn’t be charging people for that breakfast

Reviewed on Mar 22, 2026

Get rates
Heritage Hotel, Golf & Conference Center
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! (1,003 reviews)
need something in room to clean floors

Reviewed on Mar 23, 2026

Get rates
Hyatt House Shelton
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! (1,179 reviews)
Everything was wonderful. I stay at the Ethan Allen when I’m in the area. Lately it has been because my mother has had to go into long term care in Danbury. Very stressful, but at the end of the day I come back to a restful room, smiling and accommodating staff, and good food so I don’t have to go ...

Reviewed on Mar 23, 2026

Get rates
Ethan Allen Hotel
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
Book a stay at this business-friendly hotel in Southbury. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.2/10 Very Good! (1,147 reviews)
Friendly staff & comfortable room

Reviewed on Mar 22, 2026

Get rates
Wyndham Southbury
See all 677 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.