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Middletown Vacation Packages

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Middletown Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
per person
Sep 6 - Sep 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newburgh (SWF)
Book a stay at this business-friendly motel in Newburgh. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Save 100% on your flight
per person
Aug 28 - Aug 31
found 23 hours ago
Roundtrip flight included
Nashville (BNA) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Ice Time Sports Complex and Resorts World Hudson Valley are located nearby.
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newburgh (SWF)
Stay at this 4-star family-friendly hotel in Monticello. Enjoy 5 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Resorts World Catskills and Concord Monster Golf Course are located nearby.
YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Newburgh (SWF)
Stay at this 4-star spa hotel in Monticello. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Resorts World Catskills and The Kartrite Resort & Indoor Waterpark are located nearby.
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Save 100% on your flight
per person
Sep 6 - Sep 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newburgh (SWF)
Stay at this 4.5-star luxury hotel in Monticello. Enjoy a full-service spa, 6 restaurants, and a casino. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Resorts World Catskills and Concord Monster Golf Course are located nearby.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
per person
Sep 6 - Sep 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Paramount Theatre and Soons Orchards are located nearby.
Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown

2 out of 5
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.
Newburgh Inn

Newburgh Inn

2 out of 5
per person
Sep 6 - Sep 8
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and a conference center. Popular attractions Hamilton Fish Bridge and Resorts World Hudson Valley are located nearby.

Middletown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Newburgh (SWF)
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Save 100% on your flight
per person
Aug 28 - Aug 31
found 23 hours ago
Roundtrip flight included
Nashville (BNA) to Newburgh (SWF)
YO1 Longevity & Health Resorts, Catskills

YO1 Longevity & Health Resorts, Catskills

4 out of 5
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Newburgh (SWF)
Microtel Inn & Suites by Wyndham Middletown

Microtel Inn & Suites by Wyndham Middletown

2 out of 5
per person
Jul 25 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Newburgh (SWF)

Middletown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

2 out of 5
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Newburgh (SWF)
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
per person
Aug 31 - Sep 4
found 23 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Newburgh (SWF)

Top Flight Deals

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

Breeze Airways
Tue, Jul 8 - Thu, Jul 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$206 Roundtrip, just found
$206
Roundtrip
just found
Select Breeze Airways flight, departing Tue, Jul 8 from Orlando Intl. to Stewart Intl., returning Thu, Jul 10, priced at $206 just found
Breeze Airways
Thu, Jul 3 - Sun, Jul 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$212 Roundtrip, found 3 days ago
$212
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jul 3 from Orlando Intl. to Stewart Intl., returning Sun, Jul 6, priced at $212 found 3 days ago
Breeze Airways
Tue, Jul 8 - Thu, Jul 10
MCO
Orlando Intl.
SWF
Stewart Intl.
$216 Roundtrip, just found
$216
Roundtrip
just found
Select Breeze Airways flight, departing Tue, Jul 8 from Orlando Intl. to Stewart Intl., returning Thu, Jul 10, priced at $216 just found
Breeze Airways
Mon, Jul 7 - Sun, Jul 13
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$535 Roundtrip, found 4 days ago
$535
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Mon, Jul 7 from Raleigh - Durham Intl. to Stewart Intl., returning Sun, Jul 13, priced at $535 found 4 days ago