Beautiful Autumn View in Bear Mountain State Park

Holiday Homes in Middletown

  • 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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Middletown holiday homes

Interior

1. 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, (18 reviews)
"Great value and beautiful room and In ."
United States
Paul E.
The price is €137
includes taxes & fees
3 Aug - 4 Aug
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior

2. Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (20 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is €130
includes taxes & fees
6 Aug - 7 Aug
Trails Head Tiny House
TV

3. Hike & Fish: Outdoor Retreat Near Trails

Hike & Fish: Outdoor Retreat Near Trails
Wurtsboro
9.6 out of 10, Exceptional, (9 reviews)
"Nice, clean little property in a secluded area. Great to get away."
United States
David F.
The price is €361
includes taxes & fees
30 Aug - 31 Aug
Hike & Fish: Outdoor Retreat Near Trails
TV, fireplace

4. Hike, Ski & Explore: Otisville Retreat w/ Yard!

Hike, Ski & Explore: Otisville Retreat w/ Yard!
Otisville
8.0 out of 10, Very good, (3 reviews)
"Great staff, Bill was very helpful. "
United States
MARCO
The price is €558
includes taxes & fees
29 Aug - 30 Aug
Hike, Ski & Explore: Otisville Retreat w/ Yard!
Beach

5. Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.8 out of 10, Exceptional, (41 reviews)
"Very thoughtfully appointed and lovingly maintained. Excellent value with lots of extras. I travelled in July, and the lake was amazing"
United States
Olga
The price is €226
includes taxes & fees
4 Aug - 5 Aug
Beaver Lake Escape
Property grounds

6. Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
9.0 out of 10, Wonderful, (4 reviews)
"This place was amazing and our hosts were as equally as awesome as their campsite. My family highly recommends this place! It's got everything you need and is close to so many beautiful hiking and swimming areas!"
United States
Andie C.
The price is €136
includes taxes & fees
2 Aug - 3 Aug
Glamping Tent & Campsite by Minnewaska State Park
Interior

7. 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
Warwick
8.4 out of 10, Very good, (15 reviews)
"I absolutely loved my stay. A beautiful place with Victorian inspired, a big comfy bed, a really nice cozy reading nook with stone glass windows, and had an enjoyable stay!! Very easy check-in and check-out process. Great air conditioning during a heat wave!!"
United States
Daisy
The price is €135
includes taxes & fees
3 Aug - 4 Aug
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Terrace/patio

8. 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, (10 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is €359
includes taxes & fees
5 Aug - 6 Aug
House on the Babbling Brook- Quiet 2BR + King Bed!
Coffee/tea maker, fridge, microwave, oven

9. Bright Contemporary Near The Best Hiking Trails

Bright Contemporary Near The Best Hiking Trails
Pine Bush
10.0 out of 10, Exceptional, (4 reviews)
"Nice property, very close to Sam’s Point trailheads. We were there to hike, so this was perfect. We would definitely book again."
United States
Amy L.
Bright Contemporary Near The Best Hiking Trails
3 bedrooms, iron/ironing board, WiFi

10. 3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.

3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.
Goshen
8.0 out of 10, Very good, (1 review)
"The check-in process went smoothly. The property was very clean and comfortable. Location was close to many different small towns. "
United States
Kelly M.
The price is €440
includes taxes & fees
1 Aug - 2 Aug
3-bedroom house in marvelous Goshen. Luxury cabin vibes for your getaway.
Property grounds

11. Rare River Views & Access, Cabin by Eden Islands

Rare River Views & Access, Cabin by Eden Islands
Montague
9.0 out of 10, Wonderful, (14 reviews)
"Host was accessible and very nice location to enjoy what nature brings."
United Kingdom
Rohan L.
The price is €187
includes taxes & fees
4 Aug - 5 Aug
Rare River Views & Access, Cabin by Eden Islands
Exterior

12. Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out

Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Vernon Township
9.4 out of 10, Exceptional, (56 reviews)
"The area is very convenient for doing outdoor activities. Room was clean."
United States
Siyu
The price is €268
includes taxes & fees
2 Aug - 3 Aug
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Smart TV

13. The DeVita House Est. 1900

The DeVita House Est. 1900
Gardiner
10.0 out of 10, Exceptional, (36 reviews)
"Great house, well equipped, very accommodating hosts!"
United States
Christopher T.
The price is €387
includes taxes & fees
2 Aug - 3 Aug
The DeVita House Est. 1900
Living area

14. 4BD Ultimate Country Retreat w Pool in Warwick

4BD Ultimate Country Retreat w Pool in Warwick
Warwick
4BD Ultimate Country Retreat w Pool in Warwick
Interior

15. Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks

Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Kerhonkson
10.0 out of 10, Exceptional, (40 reviews)
"Sweet place, very close to Minnewaska State Park which was great for us"
United States
Sueane
The price is €189
includes taxes & fees
6 Aug - 7 Aug
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
Property grounds

16. New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi

New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
Hurleyville
10.0 out of 10, Exceptional, (3 reviews)
"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 €218
includes taxes & fees
3 Aug - 4 Aug
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
Outdoor dining

17. Forest and River Side Tranquil House

Forest and River Side Tranquil House
Montague
8.4 out of 10, Very good, (15 reviews)
"Wonderful place to relax! The location is convenient, the house is clean, cozy, and exactly as described. The hosts were very attentive and always ready to help. Great value for the price. We definitely recommend this place and would love to come back again!"
United Kingdom
Otabek K.
The price is €175
includes taxes & fees
2 Aug - 3 Aug
Forest and River Side Tranquil House
Property grounds

18. Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz

Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
wallkill
9.8 out of 10, Exceptional, (60 reviews)
"This is a wonderful property. Very clean and well maintained. It was centrally located to everything we needed. The outdoor area is amazing! We really enjoyed sitting by the river and having coffee in the morning"
United States
Nate B.
The price is €373
includes taxes & fees
26 Aug - 27 Aug
Luxe Waterfront Retreat w/ Infrared Sauna & Red Light. Near New Paltz
Interior

19. Scenic Views & River Access, Cozy River Home

Scenic Views & River Access, Cozy River Home
Montague
9.0 out of 10, Wonderful, (16 reviews)
"House was very homey feeling, very dog friendly with large yard."
United States
Catherine F.
The price is €183
includes taxes & fees
25 Aug - 26 Aug
Scenic Views & River Access, Cozy River Home
Interior

20. 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, (15 reviews)
"It was great! "It's about a whale"."
United States
jwinegra W.
The price is €199
includes taxes & fees
31 Aug - 1 Sept
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
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

Tru by Hilton Middletown

Tru by Hilton Middletown

10/10 Excellent
"It’s a compact stay with useful amenities after a long day at the parks. We stayed over for one night while visiting Lego Land. The rooms are clean and well designed with good storage. The lobby area has well thought out snacks and lounge areas to make the stay comfortable. There is a small outdoor area with table and chairs. The morning breakfast is a highlight of the stay. The breakfast is plentiful and coffee is always available. A good overnight stay with great dinner options in the area."
Diana 1-night trip
Posted 7 hours ago
Tru by Hilton Middletown

Find out more about Middletown

Middletown Holiday Homes information

Number of reviews
337
Accommodation
502 Holiday Homes
Lowest Price
€130
Highest Price
€567