Flights To Town of Southeast - Cheap Flights Starting at CA $72

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Jet to one of Town of Southeast's top cities

A windmill in a grassy field with trees in the background.

Brewster

Flights
Brewster

How Much Does it Cost To Fly To Town of Southeast?

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

Wed, Dec 30 - Tue, Jan 5
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $143 Roundtrip, found 2 days ago
CA $143
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Dec 30 from Raleigh - Durham Intl. to Westchester County, returning Tue, Jan 5, priced at CA $143 found 2 days ago
Sat, Sep 5 - Wed, Sep 9
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $152 Roundtrip, found 3 days ago
CA $152
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Sep 5 from Raleigh - Durham Intl. to Westchester County, returning Wed, Sep 9, priced at CA $152 found 3 days ago
Mon, Sep 21 - Wed, Oct 21
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $159 Roundtrip, found 1 day ago
CA $159
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Sep 21 from Raleigh - Durham Intl. to Westchester County, returning Wed, Oct 21, priced at CA $159 found 1 day ago
Sat, Sep 5 - Tue, Sep 8
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $199 Roundtrip, found 6 days ago
CA $199
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sat, Sep 5 from Raleigh - Durham Intl. to Westchester County, returning Tue, Sep 8, priced at CA $199 found 6 days ago
Sat, Sep 5 - Wed, Sep 9
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $270 Roundtrip, found 3 days ago
CA $270
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Sep 5 from Raleigh - Durham Intl. to Westchester County, returning Wed, Sep 9, priced at CA $270 found 3 days ago
Mon, Sep 21 - Wed, Oct 21
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $284 Roundtrip, found 1 day ago
CA $284
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Sep 21 from Raleigh - Durham Intl. to Westchester County, returning Wed, Oct 21, priced at CA $284 found 1 day ago
Sat, Sep 5 - Tue, Sep 8
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $325 Roundtrip, found 6 days ago
CA $325
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Sat, Sep 5 from Raleigh - Durham Intl. to Westchester County, returning Tue, Sep 8, priced at CA $325 found 6 days ago
Wed, Dec 30 - Wed, Jan 6
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $335 Roundtrip, found 2 days ago
CA $335
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Dec 30 from Raleigh - Durham Intl. to Westchester County, returning Wed, Jan 6, priced at CA $335 found 2 days ago
Tue, Aug 25 - Fri, Aug 28
YYZ
Pearson Intl.
HPN
Westchester County
CA $520 Roundtrip, found 5 days ago
CA $520
Roundtrip
found 5 days ago
Select American Airlines flight, departing Tue, Aug 25 from Pearson Intl. to Westchester County, returning Fri, Aug 28, priced at CA $520 found 5 days ago
Sat, Sep 5 - Sat, Sep 12
YYZ
Pearson Intl.
HPN
Westchester County
CA $575 Roundtrip, found 5 days ago
CA $575
Roundtrip
found 5 days ago
Select WestJet flight, departing Sat, Sep 5 from Pearson Intl. to Westchester County, returning Sat, Sep 12, priced at CA $575 found 5 days ago
Sat, Sep 5 - Tue, Sep 8
YYZ
Pearson Intl.
HPN
Westchester County
CA $597 Roundtrip, found 5 days ago
CA $597
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Sep 5 from Pearson Intl. to Westchester County, returning Tue, Sep 8, priced at CA $597 found 5 days ago
OriginDestinationTravel datesFlights from*
MCOWest HarrisonAugust 27 to August 31CA $211
MCONewburghSeptember 24 to September 30CA $217
FLLWest HarrisonOctober 7 to October 12CA $425
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCONewburghAugust 2 to August 8CA $319
MCOWest HarrisonJuly 31 to August 3CA $787
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
The High Line Hotel
4.0-star property

The High Line Hotel

Oct 8 - Oct 11

3 night stay

Toronto (YYZ) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Price was CA $2,653, price is now CA $1,590 per person
CA $1,590
per person
found 1 day ago
The Wall Street Hotel
5.0-star property

The Wall Street Hotel

Sep 15 - Sep 19

4 night stay

Ottawa (YOW) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Price was CA $4,940, price is now CA $2,729 per person
CA $2,729
per person
found 19 hours ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Sep 30 - Oct 5

5 night stay

Halifax (YHZ) to New York (JFK)

Air Canada • Non-stop roundtrip • Coach
Price was CA $3,341, price is now CA $1,969 per person
CA $1,969
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Toronto to Town of Southeast
View all trips

Travelers ❤️ These Town of Southeast 🏨

Heidi's Inn

Heidi's Inn

2.5 out of 5
1270 Route 22 Brewster NY
Book a stay at this business-friendly hotel in Brewster. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Wells Park and Brewster Public Library are located nearby.
8.8/10 Excellent! (879 reviews)
"Amazing place with staff and guests who were wonderful to interact with while enjoying gorgeous weather and outdoors"

Reviewed on Jul 28, 2026

Opens in a new windowHeidi's Inn
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 rooms in our reviews. Popular attractions Danbury Fair Mall and Xtreme Play Adventure Park are located nearby.
8/10 Very good! (1,343 reviews)
"Got a bit dingy and shabby - use to be more appealing. At least food was ok but breakfast was not included"

Reviewed on Jul 28, 2026

Opens in a new windowEthan Allen Hotel
Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Bear Mountain State Park and Monteverde at Oldstone are located nearby.
8.4/10 Very good! (1,027 reviews)
"We stayed in one of the stone cottages and were given two keys to our room and only one of the two worked. Walls are pretty thin you could hear other people's conversations. The room itself was cozy and clean and has a romantic vibe making it an ideal location for a weekend getaway with your ..."

Reviewed on Jul 27, 2026

Opens in a new windowOverlook Lodge at Bear Mountain
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
The Watershed

The Watershed

3.5 out of 5
353 Main Ave Norwalk CT
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Silvermine Arts Center and Gateway Shopping Center are located nearby.
9.2/10 Wonderful! (1,011 reviews)
"We loved our stay there! It was close to Fairfield University. We stayed for our daughter’s orientation date and it was comfortable, clean, and a quick drive to the university. We will definitely be back for future stays when visiting."

Reviewed on Jul 27, 2026

Opens in a new windowThe Watershed
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.

Frequently asked questions

How much is the cheapest flight to Town of Southeast?
Your next dream vacation doesn't have to cost a small fortune. In the last seven days, the cheapest roundtrip flight to Town of Southeast cost CA $143. Find a cheap fare and spend the cash you save on exciting experiences. This price was available on Travelocity for flights to Town of Southeast departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Town of Southeast?
There are 20 airlines that you can fly with to Town of Southeast. If you're considering a break in Brewster, pick Cape Air. This leading carrier operates 286 services every month to Town of Southeast's main city.
What is the cheapest month to fly to Town of Southeast?
December is the cheapest period to fly to Town of Southeast based on Travelocity's direct return flight demand from January to December last year. We can help you snag a fantastic deal so you can start preparing your itinerary today.
How can I check my flight status to Town of Southeast?
Make the most of our helpful portal, Trips. You'll find all things related to your flight to Town of Southeast here, including details about the status of your flight and more. You'll locate Trips at the top right of the Travelocity homepage. Simply create your free account and find the answers you're after. Alternatively, you can access your itinerary while you're on the move and get real-time travel updates with the Travelocity app. You'll find all your itineraries in one place, making it a cinch to share details with any members of your family flying with you.
How do I find the best deals on flights to Town of Southeast?
You'll always find an awesome deal with Travelocity — our "Flexible dates" function makes it considerably easier. Enter the travel dates you prefer, then click on the flexible dates box above your search results to see the prices for nearby days. CA $143 was the lowest price for a roundtrip flight to Town of Southeast in the last seven days on our site. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Town of Southeast with Travelocity?
Start packing now and get set to jet off with Travelocity. We'll help you track down the best deals on cheap flights to Town of Southeast. Whether you're chasing airfares with flexible cancellation policies or cheap family flights on budget carriers, we'll have what you're after.
What are the most popular flight routes to Town of Southeast?
As a leading tourist destination, it's a cinch to find flights to Town of Southeast. Check out this sample of major routes:

  • Nantucket, MA (ACK-Nantucket Memorial) to Westchester County Airport (HPN) - 1,265 flights a month.
  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Westchester County Airport (HPN) - 918 flights a month.
  • Chicago, IL (ORD-O'Hare Intl.) to Westchester County Airport (HPN) - 537 flights a month.

How much is a flight to Town of Southeast on average?
Passengers have found roundtrip flights to Town of Southeast for between CA $143 and CA $787 with Travelocity in the last seven days. Whether you're looking to fly budget or business class, we'll help you get a fantastic deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.