Photo by Vincent Ramundo

Holiday 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

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured Holiday Homes in Middletown

Interior
Charming bungalow in lovely Middletown NY
Charming bungalow in lovely Middletown NY
The price is NZ$340
includes taxes & fees
21 Oct - 22 Oct
Charming bungalow in lovely Middletown NY
Exterior
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
10.0 out of 10, Exceptional, (6)
"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 NZ$409
includes taxes & fees
20 Oct - 21 Oct
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
Interior
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
9.6 out of 10, Exceptional, (4)
"The Warwick Inn is an amazing stay for anyone trying to escape for a few days. The rooms were amazing, spacious, and comfortable. Gabriela was amazing at setting up our check-in and was always available for any questions we had. Highly recommend. "
United States
Nicolas
The price is NZ$262
includes taxes & fees
20 Oct - 21 Oct
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior
Dream House in the Gunks
Dream House in the Gunks
10.0 out of 10, Exceptional, (31)
"This little house is so much better in person. Clean, well outfitted and just a great restful get away. It's very quiet and so close to so many great options. Will definitely return!"
United States
meg l.
The price is NZ$434
includes taxes & fees
19 Nov - 20 Nov
Dream House in the Gunks
Outdoor spa tub
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
2.0 star property
10.0 out of 10, Exceptional, (3)
"Outstanding. "
United States
Sarah-Phil S.
The price is NZ$478
includes taxes & fees
20 Oct - 21 Oct
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
Outdoor dining
Glamping Tent & Campsite by Minnewaska State Park
Glamping Tent & Campsite by Minnewaska State Park
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 NZ$265
includes taxes & fees
20 Oct - 21 Oct
Glamping Tent & Campsite by Minnewaska State Park
Terrace/patio
perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain
perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain
2.0 star property
The price is NZ$503
includes taxes & fees
20 Oct - 21 Oct
perfect studio, few minutes away to the heart of new Paltz & Mohonk Mountain
Property grounds
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
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 NZ$415
includes taxes & fees
22 Oct - 23 Oct
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
Interior
Lovely 3BR Home with parking-Walk to WP Gate!
Lovely 3BR Home with parking-Walk to WP Gate!
10.0 out of 10, Exceptional, (6)
"Easy booking, arrival, and departure. Very nice home. Very Clean and comfortable. Host was very kind and clear on everything for stay. Will book again!"
United States
Molly s.
The price is NZ$492
includes taxes & fees
20 Oct - 21 Oct
Lovely 3BR Home with parking-Walk to WP Gate!
Exterior
House on the Babbling Brook- Quiet 2BR + King Bed!
House on the Babbling Brook- Quiet 2BR + King Bed!
10.0 out of 10, Exceptional, (2)
"Good stay, awesome place"
United States
Scott G.
The price is NZ$656
includes taxes & fees
20 Oct - 21 Oct
House on the Babbling Brook- Quiet 2BR + King Bed!
Dining
Lake Front Catskills Lodge
Lake Front Catskills Lodge
2.0 star property
The price is NZ$557
includes taxes & fees
21 Oct - 22 Oct
Lake Front Catskills Lodge
Property grounds
★Rare River Views & Access, Cabin by Eden Islands★
★Rare River Views & Access, Cabin by Eden Islands★
9.0 out of 10, Wonderful, (13)
"Nice convenient location, near the river and town. "
United States
Steve W.
The price is NZ$407
includes taxes & fees
20 Oct - 21 Oct
★Rare River Views & Access, Cabin by Eden Islands★
Shower, hair dryer
Hudson Valley Luxury | Pool, Theater, Sleeps 28
Hudson Valley Luxury | Pool, Theater, Sleeps 28
2.0 star property
The price is NZ$2,718
includes taxes & fees
20 Oct - 21 Oct
Hudson Valley Luxury | Pool, Theater, Sleeps 28
Terrace/patio
Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
9.6 out of 10, Exceptional, (4)
"Overall it was comfortable. Could have used a small table in kitchen to eat at. Wasn’t stocked with enough kitchen essentials.. two small pans needed replacing and owner was very responsive and thankful for the ideas. Beds and pillows were comfortable. Back deck had nice lighting and clean grill but lacked ambiance because of placement of garbage pails. Owner said they would move them next time. We would return but felt it was too pricey for a place with no A/C!"
United States
Anthony G.
The price is NZ$682
includes taxes & fees
21 Oct - 22 Oct
Retro Countryside Cabin | Cozy Upstate NY Private Retreat!
Terrace/patio
Sweet Old Farmhouse in a Tranquil Setting
Sweet Old Farmhouse in a Tranquil Setting
3.0 star property
10.0 out of 10, Exceptional, (1)
"Nice place - clean - good location.Owner was responsive when I called with question"
United States
Richard W.
The price is NZ$552
includes taxes & fees
20 Oct - 21 Oct
Sweet Old Farmhouse in a Tranquil Setting
Exterior
Spacious 4 bedroom house with a private pool in a quiet area
Spacious 4 bedroom house with a private pool in a quiet area
10.0 out of 10, Exceptional, (7)
"The house was very roomy and the kids just loved the layout. The host was very helpful. We appreciated that there was paper towels and a few essentials."
United States
Roberta K.
The price is NZ$761
includes taxes & fees
20 Oct - 21 Oct
Spacious 4 bedroom house with a private pool in a quiet area
Private kitchen
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
10.0 out of 10, Exceptional, (1)
"5 stars!!! 100% recommended and I will be coming back! Host is prompt, attentive, and is great with communication!! No complaints at all!!! "
United States
Fantasia
The price is NZ$1,067
includes taxes & fees
20 Oct - 21 Oct
Welcome to New Paltz. Charming 3-bedroom house with AC, WIFI,
Fridge, microwave, oven, stovetop
Marvelous 6-bedroom house with AC in Monroe
Marvelous 6-bedroom house with AC in Monroe
The price is NZ$5,975
includes taxes & fees
22 Oct - 23 Oct
Marvelous 6-bedroom house with AC in Monroe
Interior
Beaver Lake Escape
Beaver Lake Escape
9.6 out of 10, Exceptional, (29)
"This is the perfect getaway for a couple. The place is beautiful, quiet, private. Me and my husband really enjoy it "
United States
Penelope
The price is NZ$437
includes taxes & fees
20 Oct - 21 Oct
Beaver Lake Escape
Smart TV, fireplace
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
9.4 out of 10, Exceptional, (40)
"Very nice condo, had everything we needed. Included a parking pass, gym pass and pool pass. Super clean. Thanks for having us!"
United States
Louise S.
The price is NZ$531
includes taxes & fees
24 Oct - 25 Oct
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
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
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

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

10/10 Excellent
"The young man was so nice and helpful. Had a great stay. "
Holly 5-night trip
Posted 20 hours ago
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
145
Accommodation
492 Holiday Homes
Lowest Price
NZ$262
Highest Price
NZ$5,975

Explore a world of travel with Expedia