Compare Middletown Villas

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Featured Villas in Middletown

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space

Monroe NY
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. This smoke-free villa also has barbecue grills.
Pool
Hot Tub
Luxury 9BR Retreat w/Pool & Hot Tub

Luxury 9BR Retreat w/Pool & Hot Tub

Chester NY
Guests of this villa enjoy features like an outdoor pool, a hot tub, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, barbecue grills, and a garden.
Pool
Hot Tub
Family Fun Getaway near Cascade Lake in Warwick NY

Family Fun Getaway near Cascade Lake in Warwick NY

Warwick NY
Guests staying at this villa enjoy a gym, in-room fitness, and a hot tub. Other amenities at this family-friendly villa include an arcade/game room, laundry facilities, and a garden.
Pool
Hot Tub
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard

Chester NY
Guests of this villa enjoy features like an outdoor pool, a gym, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities and a garden.
Pool
Kitchen
Pool, Fire Pit Bedroom & Alaska King – Sleeps 16

Pool, Fire Pit Bedroom & Alaska King – Sleeps 16

2 out of 5
goshen NY
$731 nightly
The price is $823 total per night
$823 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
At this villa, guests have access to features like an arcade/game room. This family-friendly villa also has a garden.
Pool
Kitchen
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

2 out of 5
Monroe NY
Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills.
Pool
Hot Tub
Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery

Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery

Woodbury NY
This villa offers a gym, a sauna, and a hot tub. Other amenities at this family-friendly villa include an arcade/game room, laundry facilities, and barbecue grills.
Hot Tub
Kitchen
Lakefront Paradise w/Pool, Hot Tub, Sauna & Kayaks

Lakefront Paradise w/Pool, Hot Tub, Sauna & Kayaks

2 out of 5
Woodridge NY
Guests staying at this villa enjoy an outdoor pool, a sauna, and a hot tub. Other amenities at this family-friendly villa include an arcade/game room, laundry facilities, and a garden.
Pool
Hot Tub
Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

Harriman NY
At this villa, guests have access to an arcade/game room, laundry facilities, and a garden. This family-friendly villa also has barbecue grills.
Pool
Kitchen
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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.

Hotel Options in Middletown

    Sleep Inn & Suites Middletown - Goshen

    Sleep Inn & Suites Middletown - Goshen

    3491 Route 6 Middletown NY
    $97 nightly
    The price is $115 total per night from Jan 11 to Jan 12
    $115 total
    Jan 11 - Jan 12, 2026
    Total with taxes and fees
    8.4/10 Very Good! (1,004 reviews)
    Hampton Inn by Hilton Middletown

    Hampton Inn by Hilton Middletown

    20 Crystal Run Crossing Middletown NY
    $75 nightly
    The price is $89 total per night from Dec 28 to Dec 29
    $89 total
    Dec 28 - Dec 29
    Total with taxes and fees
    8.4/10 Very Good! (1,002 reviews)
    La Quinta Inn & Suites by Wyndham Middletown-Goshen

    La Quinta Inn & Suites by Wyndham Middletown-Goshen

    551 Route 211 E Middletown NY
    $105 nightly
    The price is $125 total per night from Dec 23 to Dec 24
    $125 total
    Dec 23 - Dec 24
    Total with taxes and fees
    9.2/10 Wonderful! (939 reviews)

Luxury Villas

Book luxury villas in Middletown
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Middletown. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Middletown, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Middletown
You won’t have a problem finding your own space in Middletown. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Middletown on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Middletown rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Middletown Villas essential information

Accommodation
26 Villas
Lowest Price
$89
Highest Price
$823
Popular accommodation
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space, Luxury 9BR Retreat w/Pool & Hot Tub, Family Fun Getaway near Cascade Lake in Warwick NY, Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard, Pool, Fire Pit Bedroom & Alaska King – Sleeps 16, Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY., Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery, Lakefront Paradise w/Pool, Hot Tub, Sauna & Kayaks, Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC

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