Middletown Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Middletown vacation rentals

Exterior

Hello Small Stone

Hello Small Stone
Middletown
9.6 out of 10, Exceptional, (5 reviews)
"The house was great. It was nice to sit and relax by the small pond in the back."
United States
John H.
The price is ￥21,079
￥59,944 total
includes taxes & fees
May 14 - May 15
Hello Small Stone
Interior

Dream getaway apartment in the foot of Gunks Ridge

Dream getaway apartment in the foot of Gunks Ridge
Wallkill
9.6 out of 10, Exceptional, (26 reviews)
"Clean and quiet."
United States
Ted
The price is ￥8,551
￥23,861 total
includes taxes & fees
May 14 - May 15
Dream getaway apartment in the foot of Gunks Ridge
Exterior

Historic Cabin with Pool & Fire Pit

Historic Cabin with Pool & Fire Pit
Montgomery
10.0 out of 10, Exceptional, (3 reviews)
"This little cabin was exactly what we needed for our stay in NY. It looks just as described, was clean, and the location was perfect for all of the places we wanted to visit. Overall it was very cozy and relaxing and we can't wait to stay again! "
United States
Sarah A.
The price is ￥16,807
￥33,596 total
includes taxes & fees
May 14 - May 15
Historic Cabin with Pool & Fire Pit
Exterior

Cabin in the heart of the Hudson Valley, Cabin 3

Cabin in the heart of the Hudson Valley, Cabin 3
Newburgh
9.8 out of 10, Exceptional, (14 reviews)
"We had a great stay, everything you need is provided. Would recommend to anyone."
United States
Bill W.
The price is ￥26,565
￥44,192 total
includes taxes & fees
May 14 - May 15
Cabin in the heart of the Hudson Valley, Cabin 3
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, (36 reviews)
"Awesome place, great location. We loved our stay."
United States
Will R.
The price is ￥12,663
￥28,013 total
includes taxes & fees
May 17 - May 18
Relaxed Mountain Living Near Minnewaska | 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
9.0 out of 10, Wonderful, (16 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 ￥13,475
￥23,804 total
includes taxes & fees
May 27 - May 28
Room 1 at The Warwick Inn – Cozy Elegance in the Heart of Town
Living area

Cozy 2BR condo w/ valley views

Cozy 2BR condo w/ valley views
Vernon Township
9.6 out of 10, Exceptional, (27 reviews)
"Very nice stay really clean and beautiful views thanks a lot enjoyed snowboarding at creek for the 2 days "
United States
Jacqueline
The price is ￥16,312
￥40,861 total
includes taxes & fees
May 14 - May 15
Cozy 2BR condo w/ valley views
Exterior

Tiny Home, King Bed & Hot Tub, Unit B

Tiny Home, King Bed & Hot Tub, Unit B
Ellenville
9.6 out of 10, Exceptional, (9 reviews)
"Everything was perfect. Don’t miss the owners restaurant either it’s great "
United States
Matthew
The price is ￥24,522
￥44,894 total
includes taxes & fees
May 14 - May 15
Tiny Home, King Bed & Hot Tub, Unit B
Fridge, oven, stovetop, coffee/tea maker

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.8 out of 10, Exceptional, (20 reviews)
"Very good communication and helpful. "
United States
Liam C.
The price is ￥18,124
￥48,363 total
includes taxes & fees
May 27 - May 28
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
1 bedroom, free WiFi, bed sheets

Cozy Loft Cabin high above Bashakill Wildlife Refuge

Cozy Loft Cabin high above Bashakill Wildlife Refuge
Wurtsboro
9.4 out of 10, Exceptional, (29 reviews)
"Great weekend getaway, very communicative and easy to access"
United States
Marlon R.
The price is ￥17,021
￥31,542 total
includes taxes & fees
Jun 8 - Jun 9
Cozy Loft Cabin high above Bashakill Wildlife Refuge
Beach

Beaver Lake Escape

Beaver Lake Escape
Rock Hill
9.6 out of 10, Exceptional, (34 reviews)
"I had a lovely getaway. "
United States
Paul J.
The price is ￥18,391
￥33,058 total
includes taxes & fees
May 14 - May 15
Beaver Lake Escape
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cabin in the Heart of the Hudson Valley, Cabin 1

Cabin in the Heart of the Hudson Valley, Cabin 1
Newburgh
10.0 out of 10, Exceptional, (32 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is ￥26,565
￥44,192 total
includes taxes & fees
May 14 - May 15
Cabin in the Heart of the Hudson Valley, Cabin 1
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 ￥24,428
￥66,108 total
includes taxes & fees
May 18 - May 19
House on the Babbling Brook- Quiet 2BR + King Bed!
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy country efficiency in the Hudson Valley

Cozy country efficiency in the Hudson Valley
Newburgh
9.8 out of 10, Exceptional, (68 reviews)
"Such a cute place to stay"
United States
Melissa
The price is ￥23,579
￥45,680 total
includes taxes & fees
May 14 - May 15
Cozy country efficiency in the Hudson Valley
TV

Cozy 1-bedroom retreat minutes from West Point!

Cozy 1-bedroom retreat minutes from West Point!
Highland Falls
10.0 out of 10, Exceptional, (2 reviews)
"Easy check in , good comms, very nice and convenient while visiting West Point (order your Uber early!) "
United States
Zack C.
The price is ￥19,361
￥35,662 total
includes taxes & fees
May 27 - May 28
Cozy 1-bedroom retreat minutes from West Point!
Interior

Trails Head Cabin

Trails Head Cabin
Rock Hill
9.8 out of 10, Exceptional, (110 reviews)
"Was very pet friendly. "
United States
Kevin
The price is ￥21,221
￥36,766 total
includes taxes & fees
May 20 - May 21
Trails Head Cabin
Property grounds

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Fort Montgomery
9.8 out of 10, Exceptional, (137 reviews)
"Amazing place Thanks for the stay "
United States
Julien C.
The price is ￥29,552
￥49,949 total
includes taxes & fees
May 28 - May 29
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Interior

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer

Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Beacon
10.0 out of 10, Exceptional, (50 reviews)
"We loved our stay. The room was so comfortable and had everything we needed. We loved being abl to walk to so many great restaurants and bars. "
United States
Amanda W.
The price is ￥18,863
￥39,631 total
includes taxes & fees
May 17 - May 18
Luxe Studio 1 Loft Main St. Beacon Luxury Steam Shower! Kitchen, Washer/Dryer
Dining

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 ￥18,174
￥32,478 total
includes taxes & fees
May 27 - May 28
Art Studio Retreat with Sauna Fireplace Forest Views | Dream House in the Gunks
1 bedroom, free WiFi, bed sheets, wheelchair access

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen

Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
Warwick
10.0 out of 10, Exceptional, (39 reviews)
"The Luxe Loft 1 is a beautiful place, meticulously cared for and appointed, and in a prime location to enjoy Warwick, NY. Communication was excellent, check-in directions clear and perfect. I can't wait to rent it again!!"
United States
Charles
The price is ￥17,684
￥40,989 total
includes taxes & fees
May 20 - May 21
Luxe Penthouse Loft on Main St- Steam Shower, Elevator, Parking, Views, Kitchen
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

Sleep Inn & Suites Monroe - Woodbury

Sleep Inn & Suites Monroe - Woodbury

10/10 Excellent
"Great place! Thank you"
Maria 1-night trip
Posted 6 hours ago
Sleep Inn & Suites Monroe - Woodbury

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

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Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find a vacation rental in Middletown?

Yes, we offer vacation rentals in Middletown close to Orange County Fairgrounds, or you can go with a more remote option if you'd like a relaxing place to stay. Visitors like the top-notch restaurants and shops in Middletown. Make sure you have time to check out the churches and architecture during your trip.

What are some of the best vacation home rentals that Middletown has to offer?

Perfect and Spacious Hudson Valley Escape!: This vacation home rental outside of Middletown has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Middletown?

With 11 Expedia vacation rentals, you're sure to find just the right place for your Middletown stay.

What’s there to see and do in Middletown?

Highland Lake and Thomas Bull Memorial Park are a couple of scenic spots to enjoy the outdoors, whereas Paramount Theatre is one of the cultural attractions. Orange County Fair Speedway and Orange County Fairgrounds are other places to visit while you're in town.

What’s a vacation rental in Middletown like?

Vacation rentals are privately owned properties you can book for short or long periods in Middletown. Vacation rentals offer extras such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.