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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Middletown vacation homes

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, (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. "
United States
Kyle T.
The price is AED 258
AED 579 total
includes taxes & fees
16 Mar - 17 Mar
Art Studio Retreat with Sauna Fireplace Forest Views | 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
9.2 out of 10, Wonderful, (10 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 311
AED 551 total
includes taxes & fees
16 Mar - 17 Mar
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Exterior

New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi

New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
Hurleyville
10.0 out of 10, Exceptional, (7 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
15 Mar - 16 Mar
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
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, (6 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AED 389
AED 1,337 total
includes taxes & fees
17 Mar - 18 Mar
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
15 Mar - 16 Mar
Trails Head Tiny House
Interior

Lux Lake Neepaulin Frontage & Panoramic Views Home

Lux Lake Neepaulin Frontage & Panoramic Views Home
Wantage
7.8 out of 10, Good, (7 reviews)
"Nice place to stay. "
United States
Bob
The price is AED 485
AED 680 total
includes taxes & fees
15 Mar - 16 Mar
Lux Lake Neepaulin Frontage & Panoramic Views Home
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
16 Mar - 17 Mar
Spacious 4 bedroom house with a private pool in a quiet area
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, (13 reviews)
"Nice convenient location, near the river and town. "
United States
Steve W.
The price is AED 345
AED 529 total
includes taxes & fees
17 Mar - 18 Mar
Rare River Views & Access, Cabin by Eden Islands
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
15 Mar - 16 Mar
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, (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 426
AED 868 total
includes taxes & fees
13 Mar - 14 Mar
Cozy private suite in the heart of beautiful Gardiner.
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 pleasant experience. "
United States
William J.
The price is AED 949
AED 1,800 total
includes taxes & fees
15 Mar - 16 Mar
Country House w/Hot Tub, Deck, Grill & Fire Pit
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
9.8 out of 10, Exceptional, (6 reviews)
"Looked like this property was recently renovated. Very clean and nice. "
United States
Ellie M.
The price is AED 496
AED 1,640 total
includes taxes & fees
17 Mar - 18 Mar
Sleek Escape: Modern 3 BR- 4 Min from West Point !
Outdoor spa tub

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi

Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Greenwood Lake
9.8 out of 10, Exceptional, (36 reviews)
"House was great, it had everything we needed and even provided coffee! "
United States
Colleen E.
The price is AED 735
AED 1,870 total
includes taxes & fees
17 Mar - 18 Mar
Waterfront Home with Hot Tub, Kayaks, and Fast Wifi
Interior

Our home is perfect for relaxing and having lots of fun, with near by activity’s

Our home is perfect for relaxing and having lots of fun, with near by activity’s
Highland
9.6 out of 10, Exceptional, (11 reviews)
"Host easy to communicate with. House spacious and conveniently located. "
United States
Susan F.
The price is AED 826
AED 2,588 total
includes taxes & fees
13 Mar - 14 Mar
Our home is perfect for relaxing and having lots of fun, with near by activity’s
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)
"We had a great time. The tent and toilet were clean. We appreciated the water provided and the cookware. The only thing to note is that there is a bit of walking on a rocky trail before reaching the campsite (not next to the parking spot). The river was fun to explore but can be difficult for younger kids to get to. The campsite is close to Minnewaska State Park, very convenient. "
United States
Angie W.
The price is AED 349
AED 597 total
includes taxes & fees
12 Apr - 13 Apr
Glamping Tent & Campsite by Minnewaska State Park
Interior

Cozy Family River Valley Retreat w/ Fireplace & Games

Cozy Family River Valley Retreat w/ Fireplace & Games
Sparrow Bush
10.0 out of 10, Exceptional, (3 reviews)
"Great stay, host was very responsive, would definitely stay again! "
United States
Shriraj S.
The price is AED 767
AED 980 total
includes taxes & fees
16 Mar - 17 Mar
Cozy Family River Valley Retreat w/ Fireplace & Games
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 1,178 total
includes taxes & fees
23 Mar - 24 Mar
Lovely 3BR Home with parking-Walk to WP Gate!
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 433
AED 634 total
includes taxes & fees
23 Mar - 24 Mar
Scenic Views & River Access, Cozy River Home
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.
The price is AED 716
AED 1,179 total
includes taxes & fees
14 Mar - 15 Mar
Pristine Country Cottage In Eldred, NY
Property grounds

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.
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

Resorts World Catskills Casino

Resorts World Catskills Casino

8/10 Good
"The kids loved the pool "
Corie 1-night trip
Posted 22 hours ago
Resorts World Catskills Casino