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Vacation rentals in Middletown, NY and nearby

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All 25 Rentals in the Middletown Area
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The following rentals are within 30 kilometres of Middletown, New York.

From
$149
Per Night
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1 / 7
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Vernon, NJ
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
From
$137
Per Night
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1 / 27
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Vernon, NJ
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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From
$249
Per Night
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1 / 8
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Ellenville
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
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From
$311
Per Night
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1 / 19
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Monticello
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautiful log cabin private setting, sit on large porch sipping your morning coffee. Warm up to a roaring fire on chilly nights. Beautiful drive up from the city (1.5 hours from Manhattan GWB) enjoy the changing foliage that fall brings to the Catskills. Or summer hikes or swimming in nearby... View all property information
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5 of 5 stars Reviewed 27 January 2015
Matteo the owner of this property was a Great Guy. Met us upon arrival, to ensure our stay was going to be a comfortable one. His home was spotless and a Perfect getaway from NYC...
5 of 5 stars Reviewed 7 July 2014
The Cabin was in perfect condition. Matt (Owner) was very nice and even offered to drop us off at the local walmart for some last minute grocercies and snacks. The fire pit added...
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From
$405
Per Night
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1 / 5
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Matamoras, PA
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Enquiry
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
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From
$374
Per Night
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1 / 5
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Monroe
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
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
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From
$123
Per Night
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1 / 27
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Vernon, NJ
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (6) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • 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
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5 of 5 stars Reviewed 10 February 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...
5 of 5 stars Reviewed 3 January 2015
This is the 3rd unit I've rented from Joe and it won't be the last. We had a great time, the condo is very cozy and impeccably clean. It's so nice to be able to eat in or out...
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From
$168
Per Night
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1 / 26
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Vernon, NJ
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Enquiry
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
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5 of 5 stars Reviewed 1 February 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 11 July 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...
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From
$146
Per Night
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1 / 8
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Forestburgh
5 Bedrooms, 3 Bathrooms, Sleeps 10
Booking
Details Make Enquiry
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
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From
$218
Per Night
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1 / 11
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Vernon, NJ
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
Details Make Enquiry
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... View all property information
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From
$148
Per Night
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1 / 19
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Vernon, NJ
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Make Enquiry
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
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From
$2,242
Per Night
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1 / 7
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Campbell Hall
6 Bedrooms, 5 Bathrooms, Sleeps 20
Details Make Enquiry
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
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From
$181
Per Night
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1 / 13
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Wallkill
1 Bedroom, 3 Bathrooms, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Housekeeping...
  • Mountain Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Spa B&B of the Hudson Valley is a boutique vacation destination that combines everything you expect from an upscale bed and breakfast, clean airy rooms, lovely living areas, and delicious breakfasts with the opportunity to benefit from spa treatments at the in-house Miracles Day Spa. Spa B&B of the... View all property information
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From
$198
Per Night
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1 / 19
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Vernon, NJ
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Welcome to the community of Black Creek Sanctuary in Mountain Creek Four Seasons Getaway Resort, it is Mountain Creek only gated neighborhood . The community is situated just across the street from the ski resort where you can ski and snowboard, snow tube, mountain bike, zoom zip lines, or visit... View all property information
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From
$162
Per Night
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1 / 25
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Monroe
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Make Enquiry
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
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From
$181
Per Night
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1 / 12
Vernon, NJ
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (4) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Gym
  • Hot Tub
  • Mountain Views
  • 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
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5 of 5 stars Reviewed 6 May 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 1 March 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...
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From
$305
Per Night
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1 / 12
Vernon, NJ
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
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
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From
$243
Per Night
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1 / 24
Vernon, NJ
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (15) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
  • Mountain Views
  • Satellite TV
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
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5 of 5 stars Reviewed 10 September 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...
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From
$224
Per Night
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1 / 8
Ellenville
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (39) Make Enquiry
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
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5 of 5 stars Reviewed 18 February 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 30 October 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...
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From
$184
Per Night
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1 / 16
Ellenville
1 Bedroom, 1 Bathroom, Sleeps 6
Details Make Enquiry
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
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From
$498
Per Night
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1 / 3
Monticello
3 Bedrooms, 1 Bathroom, Sleeps 6
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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
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From
$1,930
Per Week
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1 / 26
Otisville
7 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
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
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From
$311
Per Night
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1 / 24
Washingtonville
3 Bedrooms, 4 Bathrooms, Sleeps 20
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden
  • 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
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From
$623
Per Night
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1 / 24
Pine Bush
6 Bedrooms, 8 Bathrooms, Sleeps 16
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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
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From
$560
Per Night
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1 / 10
Monticello
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
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
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