Book Villas in Middletown, NY
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Villas in Middletown
7BR Monroe Getaway: Pool, Hot Tub, & Huge Living Space
Monroe NY
$1,394 nightly
The price is $1,577 total per night
$1,577 total
Dec 29 - Dec 30
Total with taxes and fees
This villa features an outdoor pool and a hot tub. Laundry facilities and barbecue grills are also provided.
Pool
Hot Tub
Luxury 9BR Retreat w/Pool & Hot Tub
Chester NY
This villa features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. A garden and laundry facilities are also provided.
Pool
Hot Tub
Family Fun Getaway near Cascade Lake in Warwick NY
Warwick NY
This villa features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the in-room fitness and conveniences like a garden and laundry facilities.
Pool
Hot Tub
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Chester NY
This villa features an outdoor pool and a gym. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. A garden is also provided.
Pool
Kitchen
Pool, Fire Pit Bedroom & Alaska King – Sleeps 16
goshen NY
$652 nightly
The price is $732 total per night
$732 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
A garden is available at this villa. There's fun for all ages with a playground and an arcade/game room.
Pool
Kitchen
Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.
Monroe NY
A hot tub is featured at this villa, along with laundry facilities and barbecue grills.
Malkita Aria: Mountainview Escape with Postcard-Perfect Scenery
Woodbury NY
This villa features a gym and a hot tub. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the sauna and conveniences like a garden and barbecue grills.
Hot Tub
Kitchen
Lakefront Paradise w/Pool, Hot Tub, Sauna & Kayaks
Woodridge NY
This villa features an outdoor pool and a hot tub. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the sauna and conveniences like a garden and laundry facilities.
Warm Escape, Wood Stove, HotTub, Pets, <1 Hr NYC
Harriman NY
This villa features a garden, laundry facilities, and barbecue grills.
Luxury School House Retreat With Sauna & Pool- 1HR from NYC
New Hampton NY
$1,064 nightly
The price is $1,257 total per night
$1,257 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Ski-in/ski-out access and an outdoor pool are featured at this smoke-free villa. There's fun for all ages with a playground and an arcade/game room, and families will appreciate the onsite laundry facilities. Enjoy the gym and conveniences like a garden and barbecue grills.
Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!
Monticello NY
A water park and an outdoor pool are featured at this villa. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the indoor pool and conveniences like a garden and laundry facilities.
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.
Top hotels in Middletown
La Quinta Inn & Suites by Wyndham Middletown-Goshen
551 Route 211 E Middletown NY
$122 nightly
The price is $144 total per night from Jan 4 to Jan 5
$144 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (944 reviews)
Middletown Villas essential information
Accommodation | 26 Villas |
|---|---|
Lowest Price | $85 |
Highest Price | $1,577 |
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, Luxury School House Retreat With Sauna & Pool- 1HR from NYC, Hemlock Estate: Indoor Hot Tub, Heated Pool, Game Room; Spacious, Ski & More!, Spacious 8BR Catskills Cabin w/ Game Room & Deck |
More ways to wander Middletown
Explore More Ways to Travel with Travelocity
- Hotels near LEGOLAND® New York
- Hotels near Orange County Fairgrounds
- Hotels near Harness Racing Museum and Hall of Fame
- B&B in Otisville
- Condos in Otisville
- Cottages in Otisville
- Otisville Hotels
- Hotels near Galleria at Crystal Run
- Beach Resorts & in Orange County
- Hotels with Pools in Orange County
- Pet Friendly Hotels in Orange County
- Cabins in Orange County
- Resorts in Orange County
- 3 Star Hotels in Howells
- Chalets in Howells
- Howells Hotels
- Mechanicstown Hotels
- Resorts in Mechanicstown
- Country Houses in Hunter
- Hotels near Soons Orchards
- Cabins in New Hampton
- Chalets in New Hampton
- Condos in New Hampton
- Cottages in New Hampton
- Hotels with Pools in New Hampton
- New Hampton Hotels
- Inns in New Hampton
- Rv Parks in New Hampton
- Johnson Hotels
- Hotels near Paramount Theatre
- Hotels near Castle Fun Center
- Hotels near Orange County Fair Speedway
- 4 Star Hotels in Goshen
- Farmstay in Goshen
- B&B in Goshen
- Cabins in Goshen
- Chalets in Goshen
- Condos in Goshen
- Cottages in Goshen
- Extended Stay Hotels in Goshen
- Guest Houses in Goshen
- Casino Resorts & in Goshen
- Convention Center Hotels in Goshen
- Kid Friendly Hotels in Goshen
- Gay Friendly Hotels in Goshen
- Hotels with Pools in Goshen
- Hotels with Shopping in Goshen
- Spa Resorts & in Goshen
- Hotel Wedding Venues Hotels in Goshen
- Goshen Hotels
- Inns in Goshen
- Motels in Goshen
- Rv Parks in Goshen
- Resorts in Goshen
- Chester Hotels
- Hotels near Orange County
- 3 Star Hotels in Cuddebackville
- Cuddebackville Hotels
- Campbell Hall Hotels
- Hotels near Orange County Arboretum
- Hotels near Goshen Historic Track
- 4 Star Hotels in Bloomingburg
- Bloomingburg Hotels
- Hotels near Thomas Bull Memorial Park
- Condos in Jones Beach Island
- Extended Stay Hotels in Jones Beach Island
- Historic Hotels in Wurtsboro
- Hotels with Hot Tubs in Wurtsboro
- Wurtsboro Hotels
- 3 Star Hotels in Slate Hill
- Apartments in Slate Hill
- B&B in Slate Hill
- Condos in Slate Hill
- Slate Hill Hotels
- Inns in Slate Hill
- Rv Parks in Slate Hill
- Condos in City Island
- Hostels in City Island
- Town Houses in City Island
- Florida Hotels
- New York Hotels