$48 Cheap flight deals from New York (NYC) to Windermere (ORL)

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This Weekend's Flight Deals from New York to Windermere

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Aug 30 - Thu, Sep 10
SWF
Stewart Intl.
MCO
Orlando Intl.
$193 Roundtrip, found 6 days ago
$193
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Sun, Aug 30 from Stewart Intl. to Orlando Intl., returning Thu, Sep 10, priced at $193 found 6 days ago
Sun, Aug 30 - Thu, Sep 10
EWR
Newark Liberty Intl. Airport
MCO
Orlando Intl.
$270 Roundtrip, found 1 hour ago
$270
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sun, Aug 30 from Newark Liberty Intl. Airport to Orlando Intl., returning Thu, Sep 10, priced at $270 found 1 hour ago
Sat, Aug 29 - Tue, Sep 1
LGA
LaGuardia
MCO
Orlando Intl.
$335 Roundtrip, just found
$335
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Aug 29 from LaGuardia to Orlando Intl., returning Tue, Sep 1, priced at $335 just found
Sat, Aug 29 - Tue, Sep 1
JFK
John F. Kennedy Intl.
MCO
Orlando Intl.
$410 Roundtrip, just found
$410
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 29 from John F. Kennedy Intl. to Orlando Intl., returning Tue, Sep 1, priced at $410 just found

Airfares from $48 One Way, $82 Round Trip from New York to Windermere

Prices starting at $82 for return flights and $48 for one-way flights to Windermere were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Nov 20 - Mon, Dec 7
SWF
Newburgh
SFB
Orlando
$82 Roundtrip, found 5 days ago
$82
Roundtrip
found 5 days ago
Select Allegiant Air flight, departing Fri, Nov 20 from Newburgh to Orlando, returning Mon, Dec 7, priced at $82 found 5 days ago
Tue, Oct 13 - Tue, Oct 20
EWR
New York
MCO
Orlando
$140 Roundtrip, found 7 hours ago
$140
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Oct 13 from New York to Orlando, returning Tue, Oct 20, priced at $140 found 7 hours ago
Mon, Nov 23 - Wed, Dec 9
LGA
New York
MCO
Orlando
$144 Roundtrip, found 17 hours ago
$144
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Mon, Nov 23 from New York to Orlando, returning Wed, Dec 9, priced at $144 found 17 hours ago
Wed, Sep 23 - Wed, Sep 30
SWF
Newburgh
MCO
Orlando
$150 Roundtrip, just found
$150
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Sep 23 from Newburgh to Orlando, returning Wed, Sep 30, priced at $150 just found
Tue, Jan 26 - Tue, Feb 2
HPN
White Plains
MCO
Orlando
$157 Roundtrip, found 2 days ago
$157
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Tue, Jan 26 from White Plains to Orlando, returning Tue, Feb 2, priced at $157 found 2 days ago

Windermere economy flight packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel
3.0-star property

Palazzo Lakeside Hotel

8.4/10 Very Good! (5,311 reviews)

Oct 14 - Oct 18

4 night stay

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Price was $1,009, price is now $300 per person
$300
per person
found 1 day ago
I went there. There was nowhere to park. I had to go park on the street. They say that the TV in the rooms are smart TV. That was a lie they are old and not smart.

Reviewed on Aug 26, 2026

Westgate Vacation Villas Resort
4.0-star property

Westgate Vacation Villas Resort

8.2/10 Very Good! (2,052 reviews)

Oct 11 - Oct 17

6 night stay

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $720, price is now $351 per person
$351
per person
found 2 days ago
The place was very clean organized but when I reserved the room was with 2 full size bed with a kitchen, they give me one king size bed and a sofa bed that no one can sleep on it as soon as you lay down you go almost to the floor and if you try to move was making a lot of noise, beside that when i make my reservation with expidia i made all payments in full but when I reached there they charge me $272 for the resort fee im very disappointed

Reviewed on Aug 26, 2026

Westgate Towers Resort
3.5-star property

Westgate Towers Resort

8.6/10 Excellent! (1,004 reviews)

Oct 11 - Oct 17

6 night stay

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $711, price is now $351 per person
$351
per person
found 2 days ago
Amazing to stay with family and friends. We had a storm this last visit and all the pools were closed but other than that 100% recommendation!

Reviewed on Aug 25, 2026

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Windermere first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sheraton Orlando Lake Buena Vista Resort - NEWLY RENOVATED!
4.0-star property

Sheraton Orlando Lake Buena Vista Resort - NEWLY RENOVATED!

8.8/10 Excellent! (311 reviews)

Oct 23 - Oct 26

3 night stay

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

United • Roundtrip • FirstClass
Price was $1,170, price is now $1,074 per person
$1,074
per person
found 1 day ago
Clean room nice pool close to everything

Reviewed on Aug 26, 2026

Evermore Orlando Resort
4.0-star property

Evermore Orlando Resort

9.6/10 Exceptional! (774 reviews)

Oct 23 - Oct 26

3 night stay

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

United • Roundtrip • FirstClass
Price was $2,316, price is now $2,064 per person
$2,064
per person
found 1 day ago
GREAT CUSTOMER SERVICE 👌

Reviewed on Aug 26, 2026

Rosen Centre Hotel
4.0-star property

Rosen Centre Hotel

9/10 Wonderful! (4,587 reviews)

Oct 23 - Oct 26

3 night stay

Newark Liberty Intl. Airport (EWR) to Orlando (MCO)

United • Roundtrip • FirstClass
Price was $1,390, price is now $1,283 per person
$1,283
per person
found 1 day ago
Overall, the hotel itself was very nice. Got a lot of dirty looks from the cleaning staff though. I was in town for a nearby furry convention. Every time I left my room and had my fursuit with me, and cleaning staff were nearby, it was dirty looks the whole way. I think I even got a rude comment at one point, but was hard to tell as they didn't seem to really speak English that well. The cleaning staff was also a bit too eager to let themselves into my room. They knocked on my door once, then immediately let themselves in, before anyone in my room could react.

Reviewed on Aug 26, 2026

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More About Flying To Windermere from New York

Route Information for Flights from New York to Windermere

Origin Airport IATA Code
NYC
Destination Airport IATA Code
ORL
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

New York to Windermere

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.