Photo by Vincent Ramundo

Search Vacation Homes in Middletown

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Dec - 7 Dec
In two months
16 Jan - 18 Jan
In three months
13 Feb - 15 Feb
In four months
13 Mar - 15 Mar

Vacation Homes in Middletown

Interior
Charming bungalow in lovely Middletown NY

Charming bungalow in lovely Middletown NY

Middletown
The price is SAR 506
SAR 731 total
includes taxes & fees
4 Dec - 5 Dec
Charming bungalow in lovely Middletown NY
Interior
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything

Kerhonkson
9.8 out of 10, Exceptional, (22)
"Beautiful property on a quiet block. The house is nicely stocked with everything you need and has charming decor elements. "
United States
Julia S.
The price is SAR 641
SAR 1,096 total
includes taxes & fees
4 Dec - 5 Dec
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!

House on the Babbling Brook- Quiet 2BR + King Bed!

Highland Falls
10.0 out of 10, Exceptional, (3)
"Good stay, awesome place"
United States
Scott G.
The price is SAR 458
SAR 1,454 total
includes taxes & fees
23 Nov - 24 Nov
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds
Sleek Escape: Modern 3 BR- 4 Min from West Point !

Sleek Escape: Modern 3 BR- 4 Min from West Point !

Highland Falls
10.0 out of 10, Exceptional, (2)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is SAR 518
SAR 1,622 total
includes taxes & fees
24 Nov - 25 Nov
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Interior
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

Kerhonkson
10.0 out of 10, Exceptional, (14)
"Can’t emphasize how nice the surrounding area and property itself are. Very relaxing while still being close to several small towns with great restaurants. Communication was excellent, overall a great experience! "
United States
jose f.
The price is SAR 424
SAR 764 total
includes taxes & fees
4 Dec - 5 Dec
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Exterior detail
Cozy private suite in the heart of beautiful Gardiner.

Cozy private suite in the heart of beautiful Gardiner.

New Paltz
10.0 out of 10, Exceptional, (7)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
The price is SAR 479
SAR 961 total
includes taxes & fees
23 Nov - 24 Nov
Cozy private suite in the heart of beautiful Gardiner.
Exterior
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi

New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi

Hurleyville
10.0 out of 10, Exceptional, (7)
"The house was adorable! It had all amenities. The hosts were super responsive. Definitely would stay there again. "
United States
Chris L.
The price is SAR 413
SAR 882 total
includes taxes & fees
24 Nov - 25 Nov
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
House | 7 bedrooms
West Point Villa - Jacuzzi Pool BBQ Games Pets

West Point Villa - Jacuzzi Pool BBQ Games Pets

2.0 star property
Cornwall
The price is SAR 3,571
SAR 4,355 total
includes taxes & fees
24 Nov - 25 Nov
West Point Villa - Jacuzzi Pool BBQ Games Pets
Property grounds
3BR West Point Retreat-3min to Back Gate+ King Bed

3BR West Point Retreat-3min to Back Gate+ King Bed

Highland Falls
9.0 out of 10, Wonderful, (4)
"Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. "
United States
Penny D.
The price is SAR 499
SAR 1,689 total
includes taxes & fees
3 Dec - 4 Dec
3BR West Point Retreat-3min to Back Gate+ King Bed
Outdoor dining
Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park

Kerhonkson
8.8 out of 10, Excellent, (3)
"We had a great time. The tent and toilet were clean. We appreciated the water provided and the cookware. The only thing to note is that there is a bit of walking on a rocky trail before reaching the campsite (not next to the parking spot). The river was fun to explore but can be difficult for younger kids to get to. The campsite is close to Minnewaska State Park, very convenient. "
United States
Angie W.
The price is SAR 321
SAR 569 total
includes taxes & fees
23 Nov - 24 Nov
Glamping Tent & Campsite by Minnewaska State Park
Shower, hair dryer
Hudson Valley Luxury | Pool, Theater, Sleeps 28

Hudson Valley Luxury | Pool, Theater, Sleeps 28

2.0 star property
Greenfield Park
8.0 out of 10, Very Good, (1)
"Very spacious! Clean! Kid friendly, toys, playground. Issues. In bonus apt. Horrible smell from drains.Hot tub Not working. That was big disappointing as I was looking forward to it."
United States
Stacey D.
The price is SAR 2,689
SAR 5,835 total
includes taxes & fees
2 Dec - 3 Dec
Hudson Valley Luxury | Pool, Theater, Sleeps 28
Terrace/patio
Poconos Mansion| Pool Hot Tub |Sauna |Tennis| Lake

Poconos Mansion| Pool Hot Tub |Sauna |Tennis| Lake

2.0 star property
Milford
The price is SAR 11,252
SAR 16,521 total
includes taxes & fees
7 Dec - 8 Dec
Poconos Mansion| Pool Hot Tub |Sauna |Tennis| Lake
Property grounds
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi

New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi

Hurleyville
10.0 out of 10, Exceptional, (2)
"Clean, neat, well stocked cabin in a peaceful village. We enjoyed a walk on the nearby rail trail and is not far from other interesting sites. We would definitely recommend."
United States
Holly L.
The price is SAR 413
SAR 882 total
includes taxes & fees
23 Nov - 24 Nov
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,

new paltz
9.6 out of 10, Exceptional, (4)
"Very clean Good communication with host Close to town & hiking Recommend! "
United States
Jennifer E.
The price is SAR 750
SAR 2,739 total
includes taxes & fees
4 Dec - 5 Dec
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Property grounds
Charming house with brook in the picturesque Village of Wurtsboro min from shops

Charming house with brook in the picturesque Village of Wurtsboro min from shops

Wurtsboro
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Interior
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!

2.0 star property
Warwick
10.0 out of 10, Exceptional, (3)
"Had a lovely weekend in the little red barn. And the little market next door has the best breakfast egg and bacon sandwich."
United States
michelle d.
The price is SAR 587
SAR 1,466 total
includes taxes & fees
17 Dec - 18 Dec
5 Min to Downtown Warwick, Wineries, Breweries, Hikes, Shops, & Greenwood Lake!
Fridge, microwave, oven, stovetop
★Scenic Views & River Access, Cozy River Home ★

★Scenic Views & River Access, Cozy River Home ★

Montague
9.0 out of 10, Wonderful, (11)
"Had a great time. Great location close to good food and sight seeing. We will definitely book again when good weather hits. "
United States
William H.
The price is SAR 334
SAR 728 total
includes taxes & fees
1 Dec - 2 Dec
★Scenic Views & River Access, Cozy River Home ★
Property grounds
★Rare River Views & Access, Cabin by Eden Islands★

★Rare River Views & Access, Cabin by Eden Islands★

Montague
9.0 out of 10, Wonderful, (13)
"Nice convenient location, near the river and town. "
United States
Steve W.
The price is SAR 364
SAR 767 total
includes taxes & fees
2 Dec - 3 Dec
★Rare River Views & Access, Cabin by Eden Islands★
Exterior detail
GRANDMA'S COTTAGE

GRANDMA'S COTTAGE

Monticello
9.4 out of 10, Exceptional, (18)
"I love the part that it really makes you feel like you at grandmas house and it’s close to a lot of fun things to do."
United States
Jordan
The price is SAR 675
SAR 1,197 total
includes taxes & fees
1 Dec - 2 Dec
GRANDMA'S COTTAGE
Interior
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town

Warwick
9.0 out of 10, Wonderful, (6)
"Nice to have top notch bar/restaurant downstairs!"
United States
John E
The price is SAR 311
SAR 555 total
includes taxes & fees
23 Nov - 24 Nov
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

The Kartrite Resort & Indoor Waterpark

The Kartrite Resort & Indoor Waterpark

10/10 Excellent
"Cool"
Tyrik 2-night trip
Posted 7 hours ago
The Kartrite Resort & Indoor Waterpark

Explore a world of travel with Expedia