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Next weekend
Aug 8 - Aug 10
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Aug 15 - Aug 17
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Aug 29 - Aug 31
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Sep 26 - Sep 28

Browse Select Middletown Vacation Homes

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Relax on the serene deck, surrounded by bare trees and a frozen lake.

Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views

10.0 out of 10, Exceptional, (300)
"The lake views at this house are absolutely worth the trip and the money. It's a beautiful spot. And the host, Don, is super responsive, thoughtful and accommodating. Highly recommend!"
The price is CA $561
CA $747 total
includes taxes & fees
Aug 3 - Aug 4
Cozy Lakefront Home - 278 FIVE STAR Reviews - Kayaks, Sunsets & Panoramic Views
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Enjoy a serene view of lush greenery from the bay window, accompanied by a stylish seating area with a vase of flowers.

Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town

10.0 out of 10, Exceptional, (1)
"My girlfriend and I loved our stay here! We stayed for one night and it was perfect for what we needed. Very clean with easy self-check-in. The host was very responsive with all inquiries. Short walk to nice downtown area as well!"
The price is CA $158
CA $253 total
includes taxes & fees
Aug 6 - Aug 7
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Step out onto the deck and enjoy the serene surroundings.

3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.

10.0 out of 10, Exceptional, (4)
"Lovely property in a serene and interesting setting. The hosts were so kind and communicative. We stayed for a night and enjoyed local sights and a concert in Bethel! "
The price is CA $248
CA $446 total
includes taxes & fees
Aug 5 - Aug 6
3-bedroom house in charming Forestburgh with WiFi, AC. Start your getaway now.
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Relax in a hot tub with a serene lake and forest view.

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

9.8 out of 10, Exceptional, (16)
"Clean, comfortable, beautiful views, cute little town. Super accommodating host. Couldn’t have asked for more. "
The price is CA $431
CA $914 total
includes taxes & fees
Aug 3 - Aug 4
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Terrace/patio

Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9

9.6 out of 10, Exceptional, (8)
Ultimate Lakeside Getaway on 5 Acres - Private Dock, Kayaks, Fire Pit - Sleeps 9
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Enjoy cooking in this well-equipped kitchen with a large island, oven, and stainless steel range hood.

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks

2.0 star property
9.8 out of 10, Exceptional, (11)
"My husband and I had an amazing time. Absolutely beautiful home, great location, and overall amazing experience. "
The price is CA $555
CA $821 total
includes taxes & fees
Aug 3 - Aug 4
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC
Step into the grand lobby, featuring a stunning staircase, reception desk with a lighted panel, and elegant artwork on the walls.

Charming Inn Steps away from Downtown Warwick only an Hour away from NYC

8.8 out of 10, Excellent, (5)
The price is CA $105
CA $205 total
includes taxes & fees
Aug 4 - Aug 5
Charming Inn Steps away from Downtown Warwick only an Hour away from NYC
Red Barn Retreat - Shawangunk Mountains Getaway
Enjoy al fresco dining on this outdoor deck with a barbecue grill and seating for four.

Red Barn Retreat - Shawangunk Mountains Getaway

10.0 out of 10, Exceptional, (48)
"The property is close to Minawaska State Park where we went hiking. We enjoyed the hot tub and had a nice stay. There are a number of nice restaurants nearby too."
Red Barn Retreat - Shawangunk Mountains Getaway
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
Relax in this inviting living space with a floral-patterned sofa, wooden coffee table, and a dining area.

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

9.4 out of 10, Exceptional, (32)
"Really great place for an overnight trip to Mountain Creek. Plenty of space for 2 adults, great location and access to the amenities after a long day month slopes was a total bonus. Great communication, easy access and parking. "
The price is CA $198
CA $420 total
includes taxes & fees
Aug 4 - Aug 5
Mountain Creek Lovely 1 Bedroom/Pool/Jacuzzi/King Bed/Ski In/Out
The Warwick Inn Boutique Amity Room 3 an Hour from NYC
Interior

The Warwick Inn Boutique Amity Room 3 an Hour from NYC

8.6 out of 10, Excellent, (4)
"Was happy with the room, nice property easy to walk to main street. Would stay there again."
The price is CA $139
CA $232 total
includes taxes & fees
Aug 4 - Aug 5
The Warwick Inn Boutique Amity Room 3 an Hour from NYC
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
Relax in a hot tub surrounded by lush greenery and a wooden deck.

New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space

10.0 out of 10, Exceptional, (26)
"A beautiful and bright cottage in a serene but convenient location. It was thoughtfully set up for a family getaway and was exceptionally clean. My entire family enjoyed the stay!"
The price is CA $826
CA $1,312 total
includes taxes & fees
Aug 10 - Aug 11
New 5 Bedrm/3bath + Swim Spa & Huge Outdoor Space
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
Enjoy meals in the kitchen's dining area with a wooden table and comfortable seating.

The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard

9.0 out of 10, Wonderful, (24)
"Very relaxing vibe, played some jazz albums with my coffee in the morning 😊"
The Louie II: Accord Farmhouse near Arrowood w/ Hot Tub & Large Yard
Summer Retreat: Amazing Pool, Hot Tub, Game Room, Playground!
Surrounded by lush greenery, this secluded property offers a tranquil setting with a pool and lawn.

Summer Retreat: Amazing Pool, Hot Tub, Game Room, Playground!

9.8 out of 10, Exceptional, (19)
"Secluded, quiet idyllic area, ample space for sleeping/bedrooms available, we were 10 people, clean, game room, small-ish kitchen but fully functional, bathrooms great, hot tub great, pool closed, I loved that there is a playground for kids but we were all adults, restaurants and groceries within 10-15 minute drive, we stayed for a Spartan race at Mt. Vernon only 12 minutes away, would definitely request a stay again!"
Summer Retreat: Amazing Pool, Hot Tub, Game Room, Playground!
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Experience the classic elegance of this beautifully appointed room, featuring a stunning chandelier, comfortable sofa, and elegant artwork.

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

The price is CA $163
CA $259 total
includes taxes & fees
Sep 2 - Sep 3
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
4BR Home in Highland Near Wedding Venues with Mountain Views
Enjoy a serene winter view from the comfort of your room.

4BR Home in Highland Near Wedding Venues with Mountain Views

10.0 out of 10, Exceptional, (20)
"We travelled with two other couples and everyone had their own space, privacy and yet we all hung out in the living/kitchen dining room both days! The house was spotless and the owner answered any questions within minutes! "
4BR Home in Highland Near Wedding Venues with Mountain Views
The Woodbury Cottage
Relax in a serene outdoor space surrounded by lush greenery and trees, perfect for unwinding with a hammock and golf course nearby.

The Woodbury Cottage

8.8 out of 10, Excellent, (22)
"Really enjoyed our stay at this comfy cottage. Easily slept a family of 3 with plenty of room to lounge around. It's an older cottage, but the owner has added a lot of neat touches that make this a nice place to stay in this area."
The Woodbury Cottage
Charming Highland Falls Home < 2 Mi to West Point!
Cozy cottage with a covered porch, gabled roof, and a charming garden.

Charming Highland Falls Home < 2 Mi to West Point!

10.0 out of 10, Exceptional, (9)
"What a great property! Well maintained, great amenities and close to West Point! Will definitely be back!"
Charming Highland Falls Home < 2 Mi to West Point!
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Relax in this inviting living room with a large rug, sofa, and dining area.

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

9.8 out of 10, Exceptional, (14)
"Comfortable accommodations. Everything you need for a relaxing holiday "
The price is CA $262
CA $440 total
includes taxes & fees
Sep 2 - Sep 3
Cozy Hudson Valley Retreat - 1950's Ranch Close to Everything
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Cozy living space with a fireplace, comfortable seating, and a dining area.

Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons

2.0 star property
9.2 out of 10, Wonderful, (7)
"This property is great, our stay here was just amazing from start to finish. Communication with the host was great, we left some items there and the host was super accommodating. Would recommend this property very highly."
Experience luxury shopping paradise! 4-Bedroom Home & 7 mins to Woodbury Commons
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
Enjoy a spacious room with a high ceiling, large window, and cozy dining area.

Pet-Friendly ‘Pond View Loft' w/ Private Pool!

9.6 out of 10, Exceptional, (11)
"We loved the new furniture and sheets and blankets. Everything was spotless and felt super comfortable and homey. Big space as well! "
Pet-Friendly ‘Pond View Loft' w/ Private Pool!
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

Resorts World Catskills Casino

Resorts World Catskills Casino

10/10 Excellent
"Always a great clean room"
Nicole 1-night trip
Posted 1 day ago
Resorts World Catskills Casino