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Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Middletown Vacation Homes

Glamping Tent & Campsite by Minnewaska State Park
Outdoor dining

Glamping Tent & Campsite by Minnewaska State Park

8.8 out of 10, Excellent, (3)
"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. "
The price is CA $119
CA $210 total
includes taxes & fees
Aug 21 - Aug 22
Glamping Tent & Campsite by Minnewaska State Park
Charming house with brook in the picturesque Village of Wurtsboro min from shops
Interior

Charming house with brook in the picturesque Village of Wurtsboro min from shops

Charming house with brook in the picturesque Village of Wurtsboro min from shops
Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts
Property grounds

Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts

The price is CA $99
CA $142 total
includes taxes & fees
Aug 24 - Aug 25
Okama Abon Bell Tent, River View Taino Woods 15 minutes to Bethel Woods Concerts
The Warwick Inn Boutique Amity Room 3 an Hour from NYC
Interior

The Warwick Inn Boutique Amity Room 3 an Hour from NYC

8.4 out of 10, Very good, (5)
"Was happy with the room, nice property easy to walk to main street. Would stay there again."
The price is CA $140
CA $234 total
includes taxes & fees
Sep 16 - Sep 17
The Warwick Inn Boutique Amity Room 3 an Hour from NYC
Close to Trails: Studio w/ Water Views
Exterior detail

Close to Trails: Studio w/ Water Views

10.0 out of 10, Exceptional, (4)
"Neat, clean, cozy, well stocked and enjoyable!"
The price is CA $150
CA $320 total
includes taxes & fees
Aug 31 - Sep 1
Close to Trails: Studio w/ Water Views
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308
Property grounds

Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay at the Appalachian Resort hosted by Milagros & Sergio. They were incredibly friendly and gave us clear and helpful explanations from the start. The room was very clean, and it was great having the water park within walking distance. They also offered flexible early check-in depending on the situation, which we really appreciated. Whenever we had questions, they responded very quickly, so we felt completely comfortable during our stay. We would love to come back again!"
The price is CA $173
CA $372 total
includes taxes & fees
Aug 26 - Aug 27
Condo at Mtn Creek 1 Bdr 1 Bath sleep 4 Mtn view #308
Lunar Lounge - 6 acres of green escape
Terrace/patio

Lunar Lounge - 6 acres of green escape

The price is CA $168
CA $481 total
includes taxes & fees
Aug 21 - Aug 22
Lunar Lounge - 6 acres of green escape
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Interior

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 $152
CA $248 total
includes taxes & fees
Sep 2 - Sep 3
Room 2 at The Warwick Inn – Cozy Elegance in the Heart of Town
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
Outdoor spa tub

Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,

2.0 star property
10.0 out of 10, Exceptional, (3)
"Outstanding. "
The price is CA $236
CA $378 total
includes taxes & fees
Aug 21 - Aug 22
Guest Suite 2-bedrooms with AC, Hot Tub and WiFi in peaceful Matamoras,
Country Comfort Cabin by Eden Islands
TV, fireplace

Country Comfort Cabin by Eden Islands

The price is CA $137
CA $288 total
includes taxes & fees
Aug 25 - Aug 26
Country Comfort Cabin by Eden Islands
Romantic spot above restaurant., ideal for the gourmet
Exterior

Romantic spot above restaurant., ideal for the gourmet

10.0 out of 10, Exceptional, (2)
"Highly recommended! Such a vibe, quiet & cozy. You can hear the birds in the morning, so peaceful. I would go back!! "
The price is CA $207
CA $269 total
includes taxes & fees
Aug 24 - Aug 25
Romantic spot above restaurant., ideal for the gourmet
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Exterior

Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit

10.0 out of 10, Exceptional, (1)
"Guido was very responsive and thoughtful! My partner and I stayed with our small dog and it was safe, clean, well stocked and in a beautiful area. Highly recommend to those looking to stay in the area!"
The price is CA $282
CA $420 total
includes taxes & fees
Sep 15 - Sep 16
Cozy Cabin Gateway I 1.5 Acres w. Pool & Firepit
Trails Head Tiny House
Exterior

Trails Head Tiny House

9.0 out of 10, Wonderful, (19)
"A lovely tiny house, great hosts "
The price is CA $111
CA $186 total
includes taxes & fees
Aug 26 - Aug 27
Trails Head Tiny House
Hike & Fish: Outdoor Retreat Near Trails
Exterior

Hike & Fish: Outdoor Retreat Near Trails

9.6 out of 10, Exceptional, (4)
"A wonderful stay. Comfortable beds and very clean. A short walk to a beautiful stream. We will be back!"
The price is CA $203
CA $421 total
includes taxes & fees
Aug 21 - Aug 22
Hike & Fish: Outdoor Retreat Near Trails
Hudson Valley Luxury | Pool, Theater, Sleeps 28
Shower, hair dryer

Hudson Valley Luxury | Pool, Theater, Sleeps 28

2.0 star property
The price is CA $990
CA $2,140 total
includes taxes & fees
Sep 9 - Sep 10
Hudson Valley Luxury | Pool, Theater, Sleeps 28
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
Property grounds

New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi

10.0 out of 10, Exceptional, (2)
"Clean, neat, well stocked cabin in a peaceful village. We enjoyed a walk on the nearby rail trail and is not far from other interesting sites. We would definitely recommend."
The price is CA $152
CA $319 total
includes taxes & fees
Sep 14 - Sep 15
New! Relaxing Agrihood Bungalow Getaway-Fireplace/WiFi
Fabulous 3bdrm Home w/parking!
Fridge, microwave, oven, stovetop

Fabulous 3bdrm Home w/parking!

8.0 out of 10, Very good, (2)
"Great place. Close to West Point activity. Clean and new."
The price is CA $198
CA $407 total
includes taxes & fees
Aug 21 - Aug 22
Fabulous 3bdrm Home w/parking!
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
Exterior

New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi

10.0 out of 10, Exceptional, (6)
"Only stayed overnight , but will be back , we r from tht area"
The price is CA $152
CA $319 total
includes taxes & fees
Sep 14 - Sep 15
New! Romantic Agrihood Bungalow Getaway-Fireplace/WiFi
Dream Art Studio in the Gunks
Interior

Dream Art Studio in the Gunks

10.0 out of 10, Exceptional, (12)
"A quiet, artful place for some peaceful time."
The price is CA $148
CA $268 total
includes taxes & fees
Sep 9 - Sep 10
Dream Art Studio in the Gunks
Secluded Modern Retreat
5 bedrooms, desk, free WiFi, bed sheets

Secluded Modern Retreat

The price is CA $293
CA $695 total
includes taxes & fees
Sep 2 - Sep 3
Secluded Modern Retreat
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
"Was very happy with everything and have already decided to come"
Jeffrey 1-night trip
Posted 1 day ago
Resorts World Catskills Casino