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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Middletown vacation homes

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, (15 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
22 Apr - 23 Apr
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
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 492
AED 1,470 total
includes taxes & fees
19 Apr - 20 Apr
House on the Babbling Brook- Quiet 2BR + King Bed!
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
19 Apr - 20 Apr
Trails Head Tiny House
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 611
AED 1,207 total
includes taxes & fees
11 May - 12 May
Lovely 3BR Home with parking-Walk to WP Gate!
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 590
AED 1,153 total
includes taxes & fees
11 May - 12 May
Fabulous 3bdrm Home w/parking!
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
19 Apr - 20 Apr
Glamping Tent & Campsite by Minnewaska State Park
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 290
AED 648 total
includes taxes & fees
7 May - 8 May
Relaxed Mountain Living Near Minnewaska | Dream House in the Gunks
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
21 Apr - 22 Apr
Beaver Lake Escape
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, (8 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 907 total
includes taxes & fees
20 Apr - 21 Apr
Cozy private suite in the heart of beautiful Gardiner.
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, (14 reviews)
"Nice convenient location, near the river and town. "
United States
Steve W.
The price is AED 404
AED 599 total
includes taxes & fees
19 Apr - 20 Apr
Rare River Views & Access, Cabin by Eden Islands
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 872 total
includes taxes & fees
19 Apr - 20 Apr
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
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 318
AED 639 total
includes taxes & fees
5 May - 6 May
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
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 949
AED 1,800 total
includes taxes & fees
19 Apr - 20 Apr
Country House w/Hot Tub, Deck, Grill & Fire Pit
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
19 Apr - 20 Apr
Private Mountain Creek Getaway!
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 855 total
includes taxes & fees
19 Apr - 20 Apr
Luxury home near West Point
Property grounds

Lake front on glacial lake, swimming, boating, fishing. Floating dock

Lake front on glacial lake, swimming, boating, fishing. Floating dock
Milford
7.2 out of 10, Good, (15 reviews)
"Welcoming host, helpful and good instructions for getting there "
United States
Alex R.
Lake front on glacial lake, swimming, boating, fishing. Floating dock
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
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
TV

Luxury House Near West Point

Luxury House Near West Point
Highland Falls
The price is AED 735
AED 1,188 total
includes taxes & fees
19 Apr - 20 Apr
Luxury House Near West Point
Exterior

Secluded lakefront home With an EV charger

Secluded lakefront home With an EV charger
Monticello
9.8 out of 10, Exceptional, (13 reviews)
"Wonderful place with a focus on detail and a great view. Would certainly stay again. "
United States
Russell Z.
Secluded lakefront home With an EV charger
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

Courtyard by Marriott Middletown Goshen

Courtyard by Marriott Middletown Goshen

4/10 Poor
"Our whole room felt like it needed a wipe down… there were smudges on the walls and headboard. Sheets felt and looked clean. Pool was disgusting. It was so murky you couldn’t see the bottom. And there was easily 30 kids crammed into it. Also there was flooding around the pool. "
Victoria 1-night trip
Posted 3 hours ago
Courtyard by Marriott Middletown Goshen