Middletown Holiday Homes from €109: Search Top House Rentals

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Our top choices for Middletown holiday homes

Holiday Home in Kerhonkson

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

10.0 out of 10, Exceptional, (14 reviews)

10/10

Exceptional

(14 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. "

Kyle T.

The price is €131

€131

includes taxes & fees

4 Mar - 5 Mar

Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks

3 bedrooms, desk, iron/ironing board, free WiFi

Holiday Home in Highland Falls

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

9.6 out of 10, Exceptional, (5 reviews)

9.6/10

Exceptional

(5 reviews)

"Looked like this property was recently renovated. Very clean and nice. "

Ellie M.

The price is €362

€362

includes taxes & fees

3 Mar - 4 Mar

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

Holiday Home in Hurleyville

New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"The house was adorable! It had all amenities. The hosts were super responsive. Definitely would stay there again. "

Chris L.

The price is €202

€202

includes taxes & fees

11 Mar - 12 Mar

New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi

Holiday Home in Warwick

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

9.2 out of 10, Wonderful, (9 reviews)

9.2/10

Wonderful

(9 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! "

Erin R.

The price is €133

€133

includes taxes & fees

2 Mar - 3 Mar

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

3 bedrooms, iron/ironing board, travel cot, free WiFi

Holiday Home in Goshen

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

10.0 out of 10, Exceptional, (61 reviews)

10/10

Exceptional

(61 reviews)

"This cottage was perfect for our stay. We have family nearby and this was the perfect retreat after busy days. We will be booking again. The space is clean and welcoming the land is beautiful! "

Heather A.

The price is €438

€438

includes taxes & fees

1 Mar - 2 Mar

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

Holiday Home in Montague

Rare River Views & Access, Cabin by Eden Islands

9.0 out of 10, Wonderful, (13 reviews)

9.0/10

Wonderful

(13 reviews)

"Nice convenient location, near the river and town. "

Steve W.

The price is €126

€126

includes taxes & fees

10 Mar - 11 Mar

Rare River Views & Access, Cabin by Eden Islands

Holiday Home in New Paltz

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

9.4 out of 10, Exceptional, (26 reviews)

9.4/10

Exceptional

(26 reviews)

"We stayed for wedding preparation. The space is clean and great layout for multiple guests. I am extremely satisfied with my reservation!"

Jean G.

The price is €429

€429

includes taxes & fees

11 Mar - 12 Mar

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

Holiday Home in Monroe

Hidden Lakefront Gem on a Gated Countryside Escape

2.0 star property

Hidden Lakefront Gem on a Gated Countryside Escape

Holiday Home in Rock Hill

Trails Head Tiny House

9.0 out of 10, Wonderful, (19 reviews)

9.0/10

Wonderful

(19 reviews)

"Host was very friendly and helpful. "

Michael R.

The price is €109

€109

includes taxes & fees

1 Mar - 2 Mar

Trails Head Tiny House

Holiday Home in Glen Spey

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

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Great place"

Johnny A.

The price is €372

€372

includes taxes & fees

2 Mar - 3 Mar

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

2 bedrooms, iron/ironing board, WiFi, bed sheets

Holiday Home in Highland Falls

House on the Babbling Brook- Quiet 2BR + King Bed!

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"Good stay, awesome place"

Scott G.

The price is €287

€287

includes taxes & fees

1 Mar - 2 Mar

House on the Babbling Brook- Quiet 2BR + King Bed!

3 bedrooms, iron/ironing board, WiFi, bed sheets

Holiday Home in Milford

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

7.2 out of 10, Good, (15 reviews)

7.2/10

Good

(15 reviews)

"Welcoming host, helpful and good instructions for getting there "

Alex R.

The price is €333

€333

includes taxes & fees

2 Mar - 3 Mar

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

Holiday Home in Highland Falls

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

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Lovely home, great location and space for my family to have privacy. Enjoyed the deck for morning coffee. Would book again. "

Briana T.

The price is €295

€295

includes taxes & fees

23 Mar - 24 Mar

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

Holiday Home in Rock Hill

Beaver Lake Escape

9.6 out of 10, Exceptional, (32 reviews)

9.6/10

Exceptional

(32 reviews)

"Clean place, friendly and accommodating host! "

Bryan A.

The price is €191

€191

includes taxes & fees

3 Mar - 4 Mar

Beaver Lake Escape

Holiday Home in New Paltz

Cozy private suite in the heart of beautiful Gardiner.

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Check-in was easy. Hosts very responsive to any questions and helpful to local recommendations. "

Chanah B.

The price is €206

€206

includes taxes & fees

1 Mar - 2 Mar

Cozy private suite in the heart of beautiful Gardiner.

Holiday Home in Montague

Scenic Views & River Access, Cozy River Home

9.0 out of 10, Wonderful, (12 reviews)

9.0/10

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."

ADAM K.

The price is €138

€138

includes taxes & fees

1 Mar - 2 Mar

Scenic Views & River Access, Cozy River Home

Holiday Home in Highland Falls

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

8.0 out of 10, Very good, (6 reviews)

8.0/10

Very good

(6 reviews)

"Excellent host, house is very clean. The queen and king beds are comfortable. The sound of the brook is relaxing. "

Penny D.

The price is €363

€363

includes taxes & fees

1 Mar - 2 Mar

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

Holiday Home in Highland Falls

Fabulous 3bdrm Home w/parking!

9.2 out of 10, Wonderful, (5 reviews)

9.2/10

Wonderful

(5 reviews)

"Clean home, conveniently located to West Point. Very comfortable beds. "

Danielle B.

The price is €275

€275

includes taxes & fees

2 Mar - 3 Mar

Fabulous 3bdrm Home w/parking!

Holiday Home in Wantage

Lux Lake Neepaulin Frontage & Panoramic Views Home

7.8 out of 10, Good, (7 reviews)

7.8/10

Good

(7 reviews)

"Nice place to stay. "

Bob

The price is €161

€161

includes taxes & fees

9 Mar - 10 Mar

Lux Lake Neepaulin Frontage & Panoramic Views Home

Holiday Home in Montague

Cozy Riverside View House

6.0 out of 10, (5 reviews)

6.0/10

(5 reviews)

"Great place and price. Stayed with my friends and we had a great time. The river view was amazing. House was clean and rooms were spacious. Cooktop worked fine and the dishwasher was working fine as well. Heater was functioning warm enough for 30F below. Great place and value for the stay."

Dongjoo K.

The price is €138

€138

includes taxes & fees

1 Mar - 2 Mar

Cozy Riverside View House

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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