Deals on vacations and trips to Middletown

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

The Crossroads Hotel, Newburgh

3 out of 5
Save 100% on your flight
Price was $559, price is now $432 per person
$432
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Newburgh (SWF)
A gym is featured at this hotel, along with free self parking. WiFi in public areas is free. A fireplace in the lobby is provided and the front desk is staffed around-the-clock.
Pine Brook Manor

Pine Brook Manor

2 out of 5
Save 100% on your flight
Price was $739, price is now $520 per person
$520
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Newburgh (SWF)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free local cuisine breakfast each morning. A terrace and a picnic area are also provided.
Aspiratinns Hotel & Wellness Center

Aspiratinns Hotel & Wellness Center

3 out of 5
Save 100% on your flight
Price was $1,157, price is now $841 per person
$841
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Newburgh (SWF)
A full-service spa and a restaurant are featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. The front desk is staffed around-the-clock and concierge services are on offer.
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
Save 100% on your flight
Price was $660, price is now $530 per person
$530
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Newburgh (SWF)
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $4,936, price is now $3,980 per person
$3,980
per person
May 20 - May 24
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to Newburgh (SWF)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free resort. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like valet parking and WiFi in public areas. Enjoy the seasonal outdoor pool and conveniences like a 24-hour front desk and concierge services.

Top Middletown hotels deals

La Quinta Inn & Suites by Wyndham Middletown-Goshen

La Quinta Inn & Suites by Wyndham Middletown-Goshen

3 out of 5
551 Route 211 E Middletown NY
Free Cancellation
Reserve now, pay when you stay
$109 nightly
The price is $129 total per night
$129 total
Mar 12 - Mar 13
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Sleep Inn & Suites Middletown - Goshen

Sleep Inn & Suites Middletown - Goshen

2.5 out of 5
3491 Route 6 Middletown NY
Free Cancellation
$108 nightly
The price is $128 total per night
$128 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

3 out of 5
24 Crystal Run Xing Middletown NY
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $109 total per night
$109 total
Mar 10 - Mar 11
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, express check-out, and luggage storage are also on offer.
Pool
Pet friendly
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

2.5 out of 5
20 Crystal Run Crossing Middletown NY
Free Cancellation
Reserve now, pay when you stay
$93 nightly
The price is $109 total per night
$109 total
Mar 19 - Mar 20
Total with taxes and fees
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
Tru by Hilton Middletown

Tru by Hilton Middletown

2.5 out of 5
41 Dunning Road Middletown NY
Free Cancellation
Reserve now, pay when you stay
$102 nightly
The price is $120 total per night
$120 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free English breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and free newspapers.
Breakfast included
Pet friendly
Holiday Inn Express & Suites Middletown - Goshen by IHG

Holiday Inn Express & Suites Middletown - Goshen by IHG

2.5 out of 5
20 MED PARC ROAD Middletown NY
Free Cancellation
$118 nightly
The price is $139 total per night
$139 total
Mar 15 - Mar 16
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Breakfast included
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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.

Popular places to visit

Ferris wheel at the sunset

Orange County Fairgrounds

4.5/5(4 reviews)

Enjoy an outing to Orange County Fairgrounds during your stay in Mechanicstown. Discover the area's festivals and churches.

Orange County Fairgrounds
Overview of Cold Spring and Hudson Highlands State Park in Fall, New York - October 2024

Highland Lakes State Park

You can take time to visit Highland Lakes State Park during your travels to Middletown. While in this family-friendly area, you can savor the top-notch restaurants.

Highland Lakes State Park
Lake George on a summer day, in Bolton, New York

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Middletown. While in this family-friendly area, you can savor the top-notch restaurants.

Highland Lake

Frequently asked questions

How much are vacation packages to Middletown?
Vacation packages, which include hotels and flights in Middletown, are priced from as little as $432. Turn your travel dreams into reality and lock in your trip with Travelocity today.
How long should my Middletown vacation be?
Around 2 nights is what many visitors book for their Middletown vacation. That's a great guide, but there's plenty more to explore if you allow yourself a few extra days.
Where can I get the best vacation package deals for Middletown?
It's difficult to beat Travelocity when it comes to piecing together your Middletown package deal. There are at least 400 airlines and 1,000,000 properties around the world to select from. Plan your escape now and get ready to cross another exciting destination off your must-visit list.
Why should I book my Middletown vacation package with Travelocity?
Savings, support and a stress-free booking are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to round-the-clock support. With the Travelocity Price Match Guarantee, you know you'll always get the best deal available.
Will I save money on my Middletown car rental if I book it with a hotel or flight?
With a Middletown vacation package, you can bundle your flight, car and hotel bookings and save loads. If you're in the mood to uncover the best of this fantastic destination, why not make a beeline for Times Square? This top sight is 55 mi from Middletown. With a rental car, you'll be there in no time.
Which airport is best for Middletown?
Liberty Intl. Airport (EWR) is 55 mi from the downtown area and is the starting point for many unforgettable experiences. Alternatively, LaGuardia Airport (LGA) is 55 mi away from central Middletown and Stewart Intl. Airport (SWF) is 18 mi away from central Middletown.
What is there to do in Middletown?
While veering off the tourist trail is no doubt rewarding, you shouldn't ignore the popular sights that make a place famous. Orange County Fair Speedway and Orange County Fairgrounds are just two of them in Middletown.
Where should I stay when visiting Middletown?
If you're looking for someplace comfortable to lay your head, take a look at the Holiday Inn Express & Suites Middletown - Goshen, an IHG Hotel. It's the top pick for many travelers.

Photos of local treasures

Browse Middletown vacation photos for more inspiration

Route 17 in ny is a great road to view the fall foliage
Route 17 in ny is a great road to view the fall foliage

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