Photo by Vincent Ramundo

Search Vacation Homes in Middletown

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 549 Vacation Homes in Middletown with updated reviews, rates, and availability.

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (71)
"The home was large enough to accommodate our family and it was extremely clean. We would stay there again. Communication was excellent."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

9.8 out of 10, Exceptional, (93)
"We had a wonderful family long weekend at Michele’s beautiful home in the Hudson Valley. We were there to celebrate the birthdays of my husband, son, and grandson. The house was comfortable and well equipped to make meals. Michele the host couldn’t be more responsive. There are many great hikes and wineries close by. This was a 5 star expereince enjoyed by all."
Hiking & Climbing Paradise- walking distance to Mohonk,Gunks,Minnewaska

Catskills mountain gateway house.

9.8 out of 10, Exceptional, (17)
"The house comfortably slept the six of us."
Catskills mountain gateway house.

BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

10.0 out of 10, Exceptional, (2)
"My family and I had a fantastic stay! The house was even more beautiful and spacious than we expected, making it the perfect home base for our weekend trip to Mount Peter. It was clean, cozy, and had everything we needed for a comfortable and relaxing stay. My parents live nearby in Warwick and this will definitely be my go-to VRBO recommendation for anyone visiting the area. We can’t wait to come back!"
BillyMoe’s Bungalow, A low key 3 Bedroom house with lake view.

Sun Drenched Lakefront Cove

9.2 out of 10, Wonderful, (16)
"THIS PLACE IS BEAUTIFUL AND SO CLEAN. MOST OF ALL VERY ROOMY NO ONE WAS ONE TOP OF EACH OTHER. AREA WAS SO PEACEFUL. THE ONLT THING I LEFT MY GLASSES BEHIND. BUT OTHER THEN THAT WE LOVED IT. "
Sun Drenched Lakefront Cove

Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

10.0 out of 10, Exceptional, (46)
"This is the perfect spot for us to stay visiting our West Point cadet. Cozy, clean, well-appointed, & great communication. Thanks for everything! We'll be back! :)"
Cozy cottage w/hot tub, game room & backyard. Close to West Point and Bethel.

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (36)
"Needed rest and quiet away from the city! Not only was this the perfect location, but William is a fantastic host. Great communication before and after, from directions to access and operation with kindness and generosity of spirit. Will return! "
Red Barn Retreat - Shawangunk Mountains Getaway

Bright Cornwall-On-Hudson Vacation Rental!

9.8 out of 10, Exceptional, (14)
"Nice location. Clean and comfortable. Was very cold inside when we entered (52 degrees) and I could not find an extra blanket anywhere. Everything else was great. "
Bright Cornwall-On-Hudson Vacation Rental!

Spacious Westtown Home, Firepit, Up to 10 Guest

10.0 out of 10, Exceptional, (4)
"I stayed for business and this was perfectly located for what I needed to get done in the area. "
Spacious Westtown Home, Firepit, Up to 10 Guest

Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

10.0 out of 10, Exceptional, (284)
"I visited my college aged son over the weeend for a special event and wanted to stay somewhere with a little something special rather than a hotel. This property exceeded my expectations. Even with winter still lingering, the lake view was spectacular and was highlighted by the home's back wall of windows. Also, Don is a very responsive host and made sure the home had everything you could need - grill, grill tools, pots/pans, appliances, etc. I truly appreciated the hospitality. I hope to stay...
The price is AED 1,010
AED 1,200 total
includes taxes & fees
28 Mar - 29 Mar
Private Lakefront Home With Kayaks * Stunning Sunsets * Panoramic View

Our home is perfect for relaxing and having lots of fun, with near by activity’s

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay. The host is very responsive. The location is 30 minutes from Beacon, 10 minutes from Poughkeepsie and 2 hrs from NYC. The office was a nice feature and the house has great WiFi. "
Our home is perfect for relaxing and having lots of fun, with near by activity’s

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.0 out of 10, Wonderful, (6)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

2.0 star property
9.4 out of 10, Exceptional, (3)
"This home was newly renovated and very clean. Would stay there again."
The price is AED 1,175
AED 1,668 total
includes taxes & fees
30 Mar - 31 Mar
Luxury 3-bedroom fully renovated house in Goshen with brand new furniture.

Lakefront Luxury on Greenwood Lake

10.0 out of 10, Exceptional, (129)
"We were looking for a weekend in on the lake to relax and unwind and we got exactly that. The house was beautiful, clean and well maintained. Cheryl was attentive and came to help when needed. The views of the lake were breathtaking. Couldn’t have picked a better place. We can’t wait to come back! Thank you! "
Lakefront Luxury on Greenwood Lake

Renovated House w/Hot Tub, Deck, Grill & Fire Pit

9.8 out of 10, Exceptional, (50)
"Our family had a truly wonderful winter holiday stay - our kids (3 and 5) loved having the books and toys available to use. The location was super convenient to hiking, snow tubing and indoor playareas. House was clean and the beds were very comfortable - we slept great especially after using the hot tub!"
The price is AED 1,010
AED 1,960 total
includes taxes & fees
30 Mar - 31 Mar
Renovated House w/Hot Tub, Deck, Grill & Fire Pit

Beaver Lake Escape

9.4 out of 10, Exceptional, (15)
"Greatly enjoyed our short stay. The dog bones were a nice touch for our pups. Extremely clean, great layout - we would love to return soon"
The price is AED 606
AED 928 total
includes taxes & fees
31 Mar - 1 Apr
Beaver Lake Escape

Modern Farmhouse on pristine private 12 Acres

9.6 out of 10, Exceptional, (76)
"We had a perfect stay at the beautiful farmhouse with all of the modern amenities.Outdoor space is to die for fenced in for your pup walking trails nature trails water features running streams..Cherry on top is that the listing is very generous with check-in and checkout times you can check in at 3 and you check out at 12. This feature allows for true relaxation!Book it!!"
Modern Farmhouse on pristine private 12 Acres

Dream House in the Gunks

10.0 out of 10, Exceptional, (24)
"Awesome place, great location. We loved our stay."
The price is AED 301
AED 688 total
includes taxes & fees
3 Apr - 4 Apr
Dream House in the Gunks

Cozy Rustic Farmhouse With Wood Stove

Cozy Rustic Farmhouse With Wood Stove
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.
Don't see what you're looking for?
See all available properties in Middletown
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Middletown

Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

9.0 out of 10, Wonderful, (71)
"The home was large enough to accommodate our family and it was extremely clean. We would stay there again. Communication was excellent."
Lakefront Paradise: Views, Heated Pool, Games! Summer & Winter Fun For Everyone!

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (108)
"Awesome "
The price is AED 676
AED 955 total
includes taxes & fees
31 Mar - 1 Apr
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick

Stunning 10-Acre Luxury Retreat Breathtaking Views – 4BR, 4BA Near NYC & Warwick
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.