A large steel bridge spanning a river, surrounded by trees and buildings.

Middletown Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Middletown vacation rentals

Luxury Studio | Free WiFi, bed sheets

Cottage Suites

Cottage Suites
3.0 star property
Middletown
6.6 out of 10, (7 reviews)
"It was a great place "
United States
Jose
The price is AED 461
AED 1,000 total
includes taxes & fees
1 Jul - 2 Jul
Cottage Suites
Interior

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 AED 595
AED 1,533 total
includes taxes & fees
13 Jul - 14 Jul
Hello Small Stone
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, (3 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 AED 571
AED 971 total
includes taxes & fees
22 Jul - 23 Jul
Cozy 1-bedroom retreat minutes from West Point!
TV

Walk to WP Gate + Free Parking!

Walk to WP Gate + Free Parking!
Highland Falls
9.8 out of 10, Exceptional, (24 reviews)
"Would definitely stay here again! It was a great experience!"
United States
Jodi P.
The price is AED 856
AED 1,401 total
includes taxes & fees
23 Jul - 24 Jul
Walk to WP Gate + Free Parking!
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, (9 reviews)
"Good stay, awesome place"
United States
Scott G.
The price is AED 459
AED 1,362 total
includes taxes & fees
25 Jun - 26 Jun
House on the Babbling Brook- Quiet 2BR + King Bed!
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, (139 reviews)
"The space was comfortable and clean with a great view of the Hudson River valley. Perfect for 2 people on a weekend getaway. "
United States
Meredith C.
The price is AED 727
AED 1,215 total
includes taxes & fees
25 Jun - 26 Jun
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Exterior detail

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen

Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Beacon
9.8 out of 10, Exceptional, (53 reviews)
"Have stayed a few times now… absolutely wonderful!! Clean, cozy, and comfortable! "
United States
Daniela C.
The price is AED 448
AED 896 total
includes taxes & fees
30 Jun - 1 Jul
Luxe Studio #3 on Main Street- Amazing Steam Shower! Washer/Dryer, Kitchen
Exterior detail

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer

Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Beacon
10.0 out of 10, Exceptional, (58 reviews)
"Great location and quiet just like we like it. Unit was very charming."
Canada
Thomas
The price is AED 441
AED 939 total
includes taxes & fees
1 Jul - 2 Jul
Luxe Studio 4 On Main Street -Luxury Steam Shower, Views! Kitchen, Washer/ Dryer
Exterior

Cabin in the heart of the Hudson Valley, Cabin 2

Cabin in the heart of the Hudson Valley, Cabin 2
Newburgh
9.6 out of 10, Exceptional, (36 reviews)
"This was a great place to stay with our cats for a night on our way to Vermont."
United States
George J.
The price is AED 474
AED 733 total
includes taxes & fees
28 Jun - 29 Jun
Cabin in the heart of the Hudson Valley, Cabin 2
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, (35 reviews)
"Cute, clean and perfect for our needs"
United States
Richard H.
The price is AED 621
AED 1,024 total
includes taxes & fees
28 Jun - 29 Jun
Cabin in the Heart of the Hudson Valley, Cabin 1
Smart TV

Grant - A Tranquil One Bedroom Steps from River

Grant - A Tranquil One Bedroom Steps from River
Newburgh
9.6 out of 10, Exceptional, (45 reviews)
"Great lil tranquil home. Had all the things you'd need with some bonus touches and Stan was very quick and easy to communicate with. "
United States
Jen G.
The price is AED 496
AED 1,084 total
includes taxes & fees
13 Jul - 14 Jul
Grant - A Tranquil One Bedroom Steps from River
Interior

Large,Cozy,Bright Apartment, Business Themed.

Large,Cozy,Bright Apartment, Business Themed.
Newburgh
9.0 out of 10, Wonderful, (15 reviews)
"Very cozy stay with responsive host"
United States
Adhith P.
The price is AED 1,521
AED 2,031 total
includes taxes & fees
5 Jul - 6 Jul
Large,Cozy,Bright Apartment, Business Themed.
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)
"Comfy cozy weekend retreat"
United States
Michael M.
The price is AED 551
AED 1,076 total
includes taxes & fees
25 Jun - 26 Jun
Cozy country efficiency in the Hudson Valley
Outdoor spa tub

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King

3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Cornwall
10.0 out of 10, Exceptional, (9 reviews)
"So cute and cozy!! We had the best time and loved it. "
United States
corinne n.
The price is AED 716
AED 1,471 total
includes taxes & fees
25 Jun - 26 Jun
3 Bedroom Dream: Hudson Valley views, Woodbury Commons, West Point & Storm King
Terrace/patio

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 AED 621
AED 1,024 total
includes taxes & fees
25 Jun - 26 Jun
Cabin in the heart of the Hudson Valley, Cabin 3
Outdoor dining

Cabin in the heart of the Hudson Valley, Cabin 4

Cabin in the heart of the Hudson Valley, Cabin 4
Newburgh
9.2 out of 10, Wonderful, (28 reviews)
"We LOVE this place and have stayed here twice."
United States
jennifer w.
The price is AED 474
AED 733 total
includes taxes & fees
25 Jun - 26 Jun
Cabin in the heart of the Hudson Valley, Cabin 4
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, (12 reviews)
"We had was great time and the host Mary was amazing and excellent at communicating. Everything was perfect in the home. Thank you"
United States
Pinal
The price is AED 1,131
AED 2,969 total
includes taxes & fees
29 Jun - 30 Jun
Our home is perfect for relaxing and having lots of fun, with near by activity’s
Outdoor spa tub

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

Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
New Paltz
9.6 out of 10, Exceptional, (32 reviews)
"Exactly as listed, great property and host."
United Kingdom
Neil C.
The price is AED 970
AED 1,615 total
includes taxes & fees
29 Jun - 30 Jun
Scenic New Paltz Escape: River Views, Hot Tub & Deck | Dream House in the Gunks
Cottage (2 Bedrooms) | Interior

Hudson Valley Retreat w/ Pool Near Greenwood Lake

Hudson Valley Retreat w/ Pool Near Greenwood Lake
3.0 star property
Monroe
10.0 out of 10, Exceptional, (3 reviews)
"fantastic accommodations"
United States
David
The price is AED 672
AED 1,891 total
includes taxes & fees
28 Jun - 29 Jun
Hudson Valley Retreat w/ Pool Near Greenwood Lake
Property grounds

Villa Verde B&B, Greenwood Lake NY, 1

Villa Verde B&B, Greenwood Lake NY, 1
Monroe
10.0 out of 10, Exceptional, (31 reviews)
"Great host. Home is very clean and well appointed. Would definitely stay here again."
United States
Thomas
The price is AED 882
AED 1,359 total
includes taxes & fees
30 Jun - 1 Jul
Villa Verde B&B, Greenwood Lake NY, 1
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

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

8/10 Good
"The rooms were large, staff was friendly and complimentary breakfast had a large variety of food."
Susan 1-night trip
Posted 7 hours ago
Holiday Inn Express Hotel & Suites Chester by IHG

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?

Lakefront Paradise Pool + Paddle Boats Sleeps 12: This vacation home rental outside of Middletown offers an outdoor pool, a balcony, and air-conditioning to help you feel perfectly comfortable in your new surroundings. You can relax into your vacation with a garden and a pool table.

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.