We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Middletown, NY and nearby

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 26 Rentals in the Middletown Area
    loading...
    Don't let other travelers get your favorite Middletown area vacation rental. You're so close to securing your perfect getaway. Book today.
    Sort by

    The following rentals are within 20 miles of Middletown, New York.

    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 19
    5 of 5 stars (2) Excellent
    Monticello
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    From
    $149
    / Night
    Payment Protection
    View Details
    1 / 19
    5 of 5 stars (1) Excellent
    Vernon, NJ
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    From
    $145
    / Night
    Payment Protection
    View Details
    1 / 13
    Wallkill
    1 Bedroom / 3 Bathrooms / Sleeps 2
    Overview Make Inquiry
    From
    $170
    / Night
    Payment Protection
    View Details
    1 / 4
    Arden
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Asheville River Cabins offers a truly memorable and unique experience for guests looking for the best of both worlds. Our cabins are the only cabin rentals in Asheville, NC located directly on the French Broad River, the third oldest river in the world. Our cabins provide panoramic sights and... View all property information
    Make Inquiry
    From
    $119
    / Night
    Payment Protection
    View Details
    1 / 19
    Vernon, NJ
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Hot Tub
    • Mountain Views
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Welcome to Unit 406 at The Appalachian Lodge in the beautiful mountains of Vernon NJ. This year round resort offers the areas best skiing, golfing, water park, mountain biking and lots of family friendly activities. This fully furnished unit offers you the highest ceilings of any other floor,... View all property information
    Make Inquiry
    From
    $130
    / Night
    Payment Protection
    View Details
    1 / 25
    Monroe
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Situated on 7 wooded acres, a one-bedroom cottage with full kitchen, and bath. The cottage is one of two dwellings on the property. Our family lives full time in the main house. Located near major highways, just 55 miles north of New York City. Also only 10 minutes from the world famous... View all property information
    Make Inquiry
    From
    $135
    / Night
    Payment Protection
    View Details
    1 / 26
    5 of 5 stars (2) Excellent
    Vernon, NJ
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    1 BR luxury condo, come with a cozy electric fireplace, fully equipped kitchenette,dininng room area for 6 and 2 LCD TVs, free cable, free internet, wifi, dishwasher,Mini-fridge, 2 burner cooktop, microwave, central AC. Granite countertops, and all feature private balconies overlooking the... View all property information
    Make Inquiry
    5 of 5 stars Reviewed February 1, 2015
    I thank Derrick for how amazing the place looked when we arrived. I was in Killington,VT last week and Mt. Creek was such better condition for skiing and room was so much nicer...
    5 of 5 stars Reviewed July 11, 2014
    One of our best vacations ever. The condo was clean, the whole resort was clean as well. No hassels as far as checking in because we went through tripadvisor and the owner of the...
    See all reviews
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 8
    4 of 5 stars (1) Very good
    Ellenville
    2 Bedrooms / 1 Bathroom / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Cozy 2 bedroom 1 bath cottage, sleeps 6, is available for summer rental. Beautiful wooded property leading to your private beach. Swim, fish or boat in a pristine 100 acre lake. The house is fully furnished, enclosed porch and a deck with lakeviews. Lots of hiking trails nearby. Ideal for... View all property information
    Make Inquiry
    From
    $300
    / Night
    Payment Protection
    View Details
    1 / 5
    5 of 5 stars (1) Excellent
    Monroe
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Caren House Bed and Breakfast is located 3 miles from Woodbury Commons Premium Outlets in Harriman, NY. We provide transportation to and from the Commons. We are also close to West Point Military Academy, a Jack Nicklaus Golf Course, the Applachian Trail, wineries, Orange County Choppers. We are... View all property information
    Make Inquiry
    From
    $175
    / Night
    Payment Protection
    View Details
    1 / 11
    Vernon, NJ
    3 Bedrooms / 1 Bathroom / Sleeps 8
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Hot Tub
    • Mountain Views
    • Safe
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Fall is rapidly approaching and the Winter Ski Season is just around the corner. Skiing, Golf, Horseback Riding, Minerals Spa, The Water park and more......Book Now!!!!! Fully furnished Condominium in Great Gorge Village Mountain Creek Resort The first floor consists of a Living room, Dining Room,... View all property information
    Make Inquiry
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $117
    / Night
    Payment Protection
    View Details
    1 / 8
    Forestburgh
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Woodsy Catskill Summer House in Merriewold. Merriewold is a private enclave of summer homes dating back to the late 1890's. The house was built in 1931 by John Moody, the financier. The house is in a mature pine forest, surrounded by ferns and mountain laurel. Merriewold is entirely private,... View all property information
    Make Inquiry
    From
    $119
    / Night
    Payment Protection
    View Details
    1 / 27
    5 of 5 stars (7) Excellent
    Vernon, NJ
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (7) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Welcome to The Appalachian Hotel, a 4 season ski-in/ski-out luxury hotel on the mountain. When you rent by owner, you enjoy the same Suites as the Hotel with all amenities included for a much lower price. This 1 bedroom Suite (Additional Studios and One bedrooms are also available) sleeps 4 and... View all property information
    Make Inquiry
    5 of 5 stars Reviewed April 6, 2015
    My hubby and I stayed here for a weekend getaway. It was 50 degrees out but they had the slopes open for one last weekend ski/snowboard weekend. We loved the heated outdoor pool...
    5 of 5 stars Reviewed February 10, 2015
    The unit I rented from Joe was exactly as described. Everything was clean and in good order and I had a very smooth experience. Would rent this unit again and I learned about a...
    See all reviews
    From
    $110
    / Night
    Payment Protection
    View Details
    1 / 27
    4.5 of 5 stars (2) Very good
    Vernon, NJ
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Shared Indoor Pool
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This vacation rental is in a desirable location near the Mountain Creek Ski Area/ Water Park, within walking distance of Minerals Sports Club and Elements Spa, Action Park, as well as proximity to the 7 golf courses of Crystal Springs Resort. Access to Minerals Sports Club is an additional fee,... View all property information
    Make Inquiry
    4 of 5 stars Reviewed December 3, 2014
    We stayed in Esteban's condo in October. The master bed was very comfortable. It was a cold night and we turned the heat on and it was fine. Clean condo. A bit sparse. But it was...
    5 of 5 stars Reviewed September 9, 2014
    Place was spotless. I say all the amenaties on the Listing so I brought food with me even though it was one quick stay. Wish I had more time to enjoy the hotel and awesome pool...
    See all reviews
    From
    $325
    / Night
    Payment Protection
    View Details
    1 / 5
    5 of 5 stars (2) Excellent
    Matamoras, PA
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Mountain Views
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Very private 3+ acre property with two bedrooms, 1 bath and a 400 square foot Great Room. Wood covered walls, lots of windows, expensive leather furniture, unique art throughout, cable TV with ProLogic sound system, Wi-Fi. Two miles into town. There are many restaurants and stores and a brand new... View all property information
    Make Inquiry
    From
    $1,800
    / Night
    Payment Protection
    View Details
    1 / 7
    Campbell Hall
    6 Bedrooms / 5 Bathrooms / Sleeps 20
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Set at the end of an upscale neighborhood. Our home has great space for entertaining and/or meeting space. We are minutes away from Brotherhood Winery, Woodbury Common Premium Outlets, West Point, Bear Mountain, Skiing and Golfing. We have a large great room, sunporch, back deck overlooking 18... View all property information
    Make Inquiry
    From
    $395
    / Night
    Payment Protection
    View Details
    1 / 30
    Monticello
    5 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Paddle Boards, Kayaks, Fire Pit, BBQ, Hammock and a Big Pier... We Have it All!! Welcome to Heller High Water, a five bedroom, two and a half bathroom water front property retreat located on the nine mile Swinging Bridge Lake in Monticello New York. The house is seven miles from the Village of... View all property information
    Make Inquiry
    From
    $245
    / Night
    View Details
    1 / 12
    4 of 5 stars (2) Very good
    Vernon, NJ
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Shhh! The secret is out, but not everyone knows it yet. There is finally an all year round resort that caters to the sports person providing skiing, snowboarding, mountain biking at Diablo Park, water park activities, and other fun such as golf at 7 championship courses, horseback riding and ice... View all property information
    Make Inquiry
    3 of 5 stars Reviewed March 7, 2015
    We had an amazing time on our trip. But we where staying very far up the mountain and of course is snowed three times while there. The first time we experianced the snow it was...
    See all reviews
    From
    $145
    / Night
    View Details
    1 / 12
    4.5 of 5 stars (4) Very good
    Vernon, NJ
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Fireplace
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The Appalachian at Mountain Creek offers year round vacation excitement by owner at discount rates. Ski in, ski out or snowboard in winter. Other seasons use the nearby Water Park, Freeride Mountain Biking Park, golf at seven championship courses, horseback ride or use the exciting new Zip line.... View all property information
    Make Inquiry
    5 of 5 stars Reviewed May 6, 2014
    Bill was great to communicate with and was very responsive to my initial contact as well as follow up emails. Our trip was last minute and he went out of his way to help us. The...
    4 of 5 stars Reviewed March 1, 2012
    We went for a holiday ski weekend. Although the ski conditions are not good this year, we all had a great time. The condo was large, clean and comfortable. The lodge next door...
    See all reviews
    From
    $195
    / Night
    View Details
    1 / 24
    5 of 5 stars (16) Excellent
    Vernon, NJ
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travelers have booked this property
    Overview Reviews (16) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Mountain Views
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Private country setting with great mountain views. On premises you have 1 indoor & 2 outdoor pools, golf course, minerals spa, indoor tennis, indoor basketball, racketball, game room, 2 jacuzies, steam room, sauna, indoor track, exercise room & gourmet restaurant. Close by you have horse back... View all property information
    Make Inquiry
    5 of 5 stars Reviewed March 18, 2015
    I love the place. Love the pool. I'm definitly going back this summer. It's a little pricy but I really like it. I will recommended to other people.
    5 of 5 stars Reviewed September 10, 2013
    Wasn't sure what to expect when we found it on the Internet, we had never been to Vernon New Jersey. Not a bad drive from Long Island and when we got there was pleasantly...
    See all reviews
    From
    $180
    / Night
    View Details
    1 / 8
    5 of 5 stars (39) Excellent
    Ellenville
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (39) Make Inquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Emerald Forest Bungalows is an enchanted locatin tucked away in Ellenville, NY. The White Pine is our brand new Chalet style Cabin. This unit was designed to blend perfectly with our forested landscape (we have just under 75 acres to frolic in). Ellenville is just a 2 hour drive north of... View all property information
    Make Inquiry
    5 of 5 stars Reviewed February 18, 2015
    The remote location of the chalet and property were exactly what we were seeking for a long weekend escape from Manhattan, yet it was very conveniently located for exploring...
    5 of 5 stars Reviewed October 30, 2014
    Trust me, you will not be disappointed! Beautiful area, wonderful chalet, great little town with plenty of restaurants, Mike/Jake is a great host, you could not ask for a more...
    See all reviews
    Get the List
    From
    $250
    / Night
    View Details
    1 / 24
    Washingtonville
    3 Bedrooms / 4 Bathrooms / Sleeps 20
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Garden or Yard
    • Grill
    • Hot Tub
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    The perfect vacation home nestled in storybook woods just 60 miles from New York City. Find yourself surrounded by luxury within and lush greenery without. Spacious yet cozy, fully-furnished rooms are ideal for relaxation: TV and home entertainment system, kitchen with breakfast area, formal... View all property information
    Make Inquiry
    From
    $400
    / Night
    View Details
    1 / 3
    Monticello
    3 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Idyllic Catskill romantic hideaway, 19 acres, private lake next to designer house, minutes from Monticello raceway and casino and Bethel Woods, 2-3 bedrooms, 90 minutes from Manhattan, Memorial Day to Labor Day, $12,000, no pets. View all property information
    Make Inquiry
    From
    $500
    / Night
    View Details
    1 / 24
    Pine Bush
    6 Bedrooms / 8 Bathrooms / Sleeps 16
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This incredible, newly-built home is nestled on three sides by private old growth forest with a meadow on the southern side for maximum solar gain in winter. Large white oak trees hug the southern side providing natural cooling shade in summer. The radiant floor heat along with other energy... View all property information
    Make Inquiry
    From
    $1,550
    / Week
    View Details
    1 / 26
    Otisville
    7 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This 7 bedroom 1920s Farmhouse style home has a dream wrap around, screened in porch which is 100 feet from the lake. Art deco wall sconces, a wood beam salon ceiling, and an open face wood stove set against an old stone fireplace add character to this rustic,charming old fashioned 1920s home. The... View all property information
    Make Inquiry
    From
    $148
    / Night
    View Details
    1 / 16
    Ellenville
    1 Bedroom / 1 Bathroom / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The deluxe lodge is located on our amenity filled resort and includes a private bedroom with a queen-sized bed. An 8' x 12' carpeted loft for kids with 3 pull-out single mattresses. A full kitchen and living room with a double-bed futon sofa, hardwood floors and a 8' x 12' screened in porch! There... View all property information
    Make Inquiry
    From
    $450
    / Night
    View Details
    1 / 10
    Monticello
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The home is located in Monticello New York on Swinging Bridge Lake in the Catskills, just 10 miles from the Monticello Gambling Casino and Bethel Woods Center for the Arts. It is located adjacent to an eagle preserve as close to the water as you can get! This lake-house features a multilevel cedar... View all property information
    Make Inquiry