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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.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $318, price is now $242 per person
$242
per person
Jan 6 - Jan 10
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Book a stay at this business-friendly hotel in Newburgh. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. Popular attractions Ice Time Sports Complex and Resorts World Hudson Valley are located nearby.
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
Save 100% on your flight
Price was $382, price is now $275 per person
$275
per person
Jan 6 - Jan 10
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Stay at this hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions LEGOLAND® New York and Galleria at Crystal Run are located nearby.
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
Price was $601, price is now $468 per person
$468
per person
Feb 22 - Mar 1
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Stay at this hotel in New Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Hamilton Fish Bridge and National Purple Heart Hall of Honor are located nearby.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $329, price is now $262 per person
$262
per person
Jan 22 - Jan 25
found 23 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
Price was $395, price is now $324 per person
$324
per person
Jan 2 - Jan 6
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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
Price was $348, price is now $295 per person
$295
per person
Jan 6 - Jan 10
found 7 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Super 8 by Wyndham Montgomery Maybrook

Super 8 by Wyndham Montgomery Maybrook

2.5 out of 5
Price was $362, price is now $316 per person
$316
per person
Jan 2 - Jan 6
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $1,821, price is now $1,618 per person
$1,618
per person
Jan 9 - Jan 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Book a stay at this luxury resort in Gardiner. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Tuthilltown Spirits and DM Weil Gallery are located nearby.

Middletown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
Price was $318, price is now $242 per person
$242
per person
Jan 6 - Jan 10
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
Save 100% on your flight
Price was $382, price is now $275 per person
$275
per person
Jan 6 - Jan 10
found 7 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Price was $329, price is now $262 per person
$262
per person
Jan 22 - Jan 25
found 23 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)
Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

Super 8 by Wyndham Newburgh/West Point Near Stewart Airport

2 out of 5
Price was $395, price is now $324 per person
$324
per person
Jan 2 - Jan 6
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Newburgh (SWF)

Middletown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Save 100% on your flight
Price was $474, price is now $301 per person
$301
per person
Jan 7 - Jan 13
found 14 hours ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Newburgh (SWF)
Homewood Suites Stewart Airport

Homewood Suites Stewart Airport

3 out of 5
Price was $601, price is now $468 per person
$468
per person
Feb 22 - Mar 1
found 5 hours ago
Roundtrip flight included
Dallas (DFW) to Newburgh (SWF)

Top Flight Deals

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

Breeze Airways
Fri, Jan 9 - Mon, Jan 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$98 Roundtrip, found 5 days ago
$98
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Jan 9 from Orlando Intl. to Stewart Intl., returning Mon, Jan 12, priced at $98 found 5 days ago
Breeze Airways
Fri, Jan 9 - Mon, Jan 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$109 Roundtrip, found 5 days ago
$109
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Jan 9 from Orlando Intl. to Stewart Intl., returning Mon, Jan 12, priced at $109 found 5 days ago
Breeze Airways
Sun, Jan 11 - Mon, Jan 12
MCO
Orlando Intl.
SWF
Stewart Intl.
$112 Roundtrip, found 22 hours ago
$112
Roundtrip
found 22 hours ago
Select Breeze Airways flight, departing Sun, Jan 11 from Orlando Intl. to Stewart Intl., returning Mon, Jan 12, priced at $112 found 22 hours ago
Breeze Airways
Wed, Jan 7 - Sun, Jan 11
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$518 Roundtrip, found 4 days ago
$518
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Jan 7 from Raleigh - Durham Intl. to Stewart Intl., returning Sun, Jan 11, priced at $518 found 4 days ago