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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Middletown vacation homes

Interior

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, (34 reviews)
"Awesome place, great location. We loved our stay."
United States
Will R.
The price is AED 200
AED 558 total
includes taxes & fees
15 Apr - 16 Apr
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
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, (12 reviews)
"I really enjoyed my stay. The room was very clean, the inn is well located in town and it is great having the restaurant below. Would stay here again! "
United States
Erin R.
The price is AED 304
AED 544 total
includes taxes & fees
12 Apr - 13 Apr
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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, (15 reviews)
"Beautiful place tucked back in the woods. Very relaxing and incredibly clean. The free coffee was a nice touch too. Will 100% be returning to The Gunks because of this house. "
United States
Kyle T.
The price is AED 284
AED 605 total
includes taxes & fees
16 Apr - 17 Apr
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
Interior

Trails Head Tiny House

Trails Head Tiny House
Rock Hill
9.0 out of 10, Wonderful, (19 reviews)
"Host was very friendly and helpful. "
United States
Michael R.
The price is AED 261
AED 457 total
includes taxes & fees
12 Apr - 13 Apr
Trails Head Tiny House
Terrace/patio

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, (8 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AED 500
AED 1,478 total
includes taxes & fees
13 Apr - 14 Apr
House on the Babbling Brook- Quiet 2BR + King Bed!
Property grounds

Glamping Tent & Campsite by Minnewaska State Park

Glamping Tent & Campsite by Minnewaska State Park
Kerhonkson
8.8 out of 10, Excellent, (3 reviews)
"This is an "upgraded" camping experience! A peaceful setting for outdoor living, exceptionally private. Super convenient to Minnewaska. Everything you need amd exactly as described, plenty of seating for a larger group and sleeping tent/yurt makes inclement weather less of a concern than a regular tent or backpacking setup. Definitely stay here!"
United States
Megan
The price is AED 314
AED 557 total
includes taxes & fees
22 Apr - 23 Apr
Glamping Tent & Campsite by Minnewaska State Park
Exterior

New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi

New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
Hurleyville
10.0 out of 10, Exceptional, (9 reviews)
"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 AED 404
AED 848 total
includes taxes & fees
29 Apr - 30 Apr
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
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 reviews)
"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "
United States
Chanah B.
The price is AED 450
AED 895 total
includes taxes & fees
22 Apr - 23 Apr
Cozy private suite in the heart of beautiful Gardiner.
Beach

Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.6 out of 10, Exceptional, (33 reviews)
"Clean place, friendly and accommodating host! "
United States
Bryan A.
The price is AED 512
AED 866 total
includes taxes & fees
12 Apr - 13 Apr
Beaver Lake Escape
Interior

Lovely 3BR Home with parking-Walk to WP Gate!

Lovely 3BR Home with parking-Walk to WP Gate!
Highland Falls
10.0 out of 10, Exceptional, (7 reviews)
"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "
United States
Briana T.
The price is AED 597
AED 1,182 total
includes taxes & fees
14 Apr - 15 Apr
Lovely 3BR Home with parking-Walk to WP Gate!
3 bedrooms, desk, iron/ironing board, free WiFi

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

Sleek Escape: Modern 3 BR- 4 Min from West Point !
Highland Falls
9.2 out of 10, Wonderful, (7 reviews)
"The host was prompt and attentive to any questions that arose. The home appeared exactly as depicted in the pictures and was perfect for a weekend stay close to family and The city!"
United States
Julio J.
The price is AED 555
AED 1,707 total
includes taxes & fees
13 Apr - 14 Apr
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Exterior

Luxury home near West Point

Luxury home near West Point
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations are great—Very nice townhouse, lots of room, clean, comfortable, and pet-friendly."
United States
Suzy
The price is AED 731
AED 851 total
includes taxes & fees
13 Apr - 14 Apr
Luxury home near West Point
Exterior detail

Fabulous 3bdrm Home w/parking!

Fabulous 3bdrm Home w/parking!
Highland Falls
9.2 out of 10, Wonderful, (5 reviews)
"Clean home, conveniently located to West Point. Very comfortable beds. "
United States
Danielle B.
The price is AED 576
AED 1,079 total
includes taxes & fees
14 Apr - 15 Apr
Fabulous 3bdrm Home w/parking!
Interior

Scenic Views & River Access, Cozy River Home

Scenic Views & River Access, Cozy River Home
Montague
9.0 out of 10, Wonderful, (12 reviews)
"We were visiting for our daughtets wedding and needed a place mearby that accommodates pets. Nothing to look at on the outside but the inside is very nice. Very comfortableorganized and a good selection of teas and some coffee."
United States
ADAM K.
The price is AED 459
AED 664 total
includes taxes & fees
12 Apr - 13 Apr
Scenic Views & River Access, Cozy River Home
Outdoor spa tub

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

Country House w/Hot Tub, Deck, Grill & Fire Pit
Goshen
10.0 out of 10, Exceptional, (61 reviews)
"Very good host "
United States
Binyomin
The price is AED 950
AED 1,834 total
includes taxes & fees
29 Apr - 30 Apr
Country House w/Hot Tub, Deck, Grill & Fire Pit
TV, fireplace

Pristine Country Cottage In Eldred, NY

Pristine Country Cottage In Eldred, NY
Highland
10.0 out of 10, Exceptional, (4 reviews)
"The cottage was well set up for a quiet and cozy weekend in the woods. "
United States
Veronica R.
Pristine Country Cottage In Eldred, NY
Exterior detail

Spacious 4 bedroom house with a private pool in a quiet area

Spacious 4 bedroom house with a private pool in a quiet area
Glen Spey
10.0 out of 10, Exceptional, (7 reviews)
"Great place"
United States
Johnny A.
The price is AED 731
AED 1,627 total
includes taxes & fees
20 Apr - 21 Apr
Spacious 4 bedroom house with a private pool in a quiet area
Interior

Private Mountain Creek Getaway!

Private Mountain Creek Getaway!
Vernon Township
8.8 out of 10, Excellent, (6 reviews)
"This place is fantastic, Charlie was extremely helpful and went above and beyond to ensure our stay was satisfactory. This place includes a lot in your stay such as towels soap/shampoo and even cotton swabs. This place is a great location and will 100% recommend for anyone staying in the area. We will definitely book again at this place and so should you if you want privacy and a great stay with a fantastic host. Thank You Charlie for the warm welcome."
United States
Cristian S.
The price is AED 625
AED 1,498 total
includes taxes & fees
12 Apr - 13 Apr
Private Mountain Creek Getaway!
Smart TV, books, stereo

Cozy little retreat far from the city

Cozy little retreat far from the city
Mountain Dale
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home VERY CLEAN neighborhood was quite was everything we were looking for would definitely stay here again and recommend to others "
United States
Chris G.
The price is AED 437
AED 719 total
includes taxes & fees
22 Apr - 23 Apr
Cozy little retreat far from the city
TV, fireplace

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

3BR West Point Retreat-3min to Back Gate+ King Bed
Highland Falls
8.0 out of 10, Very Good, (6 reviews)
"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 AED 566
AED 1,799 total
includes taxes & fees
13 Apr - 14 Apr
3BR West Point Retreat-3min to Back Gate+ King Bed
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.
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Top Middletown Hotel Reviews

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

6/10 Okay
"Have not had this experience with Hampton before. It was like staying at a motel. Bedding, sheets, bed itself, bathroom were very low quality. Everything in the room was very low quality. And it is not cheap. "
Ahmed 2-night trip
Posted 2 hours ago
Hampton Inn by Hilton Middletown