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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 Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
Price was $240, price is now $189 per person
$189
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Stay at this motel in Middletown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Galleria at Crystal Run and Orange County Fairgrounds are located nearby.
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
Save 100% on your flight
Price was $679, price is now $444 per person
$444
per person
Nov 27 - Nov 30
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Stay at this 4-star family-friendly hotel in Monticello. Enjoy 5 restaurants, 2 bars/lounges, and water park access (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.
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Save 100% on your flight
Price was $501, price is now $350 per person
$350
per person
Dec 11 - Dec 14
found 8 hours ago
Roundtrip flight included
Orlando (MCO) 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.
Cottage Suites

Cottage Suites

2 out of 5
Price was $288, price is now $228 per person
$228
per person
Jan 6 - Jan 9
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Stay at this hotel in Middletown. Enjoy free WiFi. Popular attractions Paramount Theatre and Orange County Fair Speedway are located nearby.
Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
Price was $247, price is now $198 per person
$198
per person
Dec 11 - Dec 14
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Book a stay at this business-friendly motel in Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions City Winery Hudson Valley and Orange County Farmers Museum are located nearby.
Candlewood Suites Middletown Goshen by IHG

Candlewood Suites Middletown Goshen by IHG

2.5 out of 5
Save 100% on your flight
Price was $489, price is now $394 per person
$394
per person
Dec 11 - Dec 14
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Stay at this hotel in Middletown. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

2.5 out of 5
Price was $425, price is now $345 per person
$345
per person
Dec 11 - Dec 14
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Chester. 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 Castle Fun Center are located nearby.
La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
Price was $517, price is now $422 per person
$422
per person
Dec 29 - Jan 2
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Stay at this 3-star 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 Galleria at Crystal Run and Orange County Fairgrounds are located nearby.

Middletown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Middletown

Super 8 by Wyndham Middletown

2.5 out of 5
Price was $240, price is now $189 per person
$189
per person
Dec 6 - Dec 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

4 out of 5
Save 100% on your flight
Price was $679, price is now $444 per person
$444
per person
Nov 27 - Nov 30
found 2 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Save 100% on your flight
Price was $501, price is now $350 per person
$350
per person
Dec 11 - Dec 14
found 8 hours ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $301, price is now $222 per person
$222
per person
Dec 11 - Dec 14
found 8 hours ago
Roundtrip 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.
Howard Johnson by Wyndham Newburgh/West Point

Howard Johnson by Wyndham Newburgh/West Point

2 out of 5
Price was $422, price is now $345 per person
$345
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Courtyard by Marriott Newburgh Stewart Airport

Courtyard by Marriott Newburgh Stewart Airport

3 out of 5
Price was $699, price is now $562 per person
$562
per person
Nov 23 - Nov 29
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $430, price is now $358 per person
$358
per person
Nov 23 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newburgh (SWF)
Resorts World Catskills Casino

Resorts World Catskills Casino

4.5 out of 5
Price was $1,331, price is now $1,118 per person
$1,118
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Newburgh (SWF)

Top Flight Deals

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

Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$133 Roundtrip, found 8 hours ago
$133
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $133 found 8 hours ago
Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$137 Roundtrip, found 3 days ago
$137
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $137 found 3 days ago
Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$138 Roundtrip, found 8 hours ago
$138
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $138 found 8 hours ago
Breeze Airways
Thu, Dec 4 - Sun, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
$142 Roundtrip, found 3 days ago
$142
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Dec 4 from Orlando Intl. to Stewart Intl., returning Sun, Dec 7, priced at $142 found 3 days ago