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USA  USA - Holiday Rentals in Hudson Valley Fl USA
USA Country: USA (4033) | Region: Florida (1116)
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    Found 21 Hudson Valley Fl properties for vacation rental

    Hudson Valley FL, Cottage for rent
    Cottage • 10 People • 4 • 3 • pets pool wifi
    From
    $
    4,228 USD /night
    Min Stay 2 nights


    View Details

    Hudson Valley FL, USA 

    $ 4,228 USD /Night (minimum stay 2 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Hawk - Falcon

    Unplug, tune out and drop off the grid for a while. Nestled out of the way in the Rondout Valley in Upstate New York, this secluded barn house and cottage combo is perfect for anyone looking to get away from it all. Sat within seventy-five acres of idyllic woodland, the scene is set for you to live out your Captain Fantastic fantasies. There's even a renovated bus to sleep in (available to rent separately). Host Casey has built fairytale hangouts to immerse you in nature, including a hammock overlooking a waterfall, a gazebo beside a lily pond, and a yoga platform in the woods. The barn decking and outdoor kitchen adorned with fairy lights is a magical spot for family meals. Entertaining the family is easy with fireside songs (your hosts recommend making s'mores with Tate's Cookies instead of Graham Crackers – you can thank them later), swims in the pool and indoor and outdoor games for all ages to enjoy. We fully envision your kids dau...More Details


      • Booked Available
    Hudson Valley FL, House for rent
    House • 6 People • 3 • 2 • pets wifi
    From
    $
    3,244 USD /night
    Min Stay 2 nights


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    Hudson Valley FL, USA 

    $ 3,244 USD /Night (minimum stay 2 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    Quilted Star

    Looking a little like the house from Grant Wood's famous American Gothic – and with a pared-down rustic interior to match – this extraordinary rural retreat is perfect for those looking to escape the trappings of modern life, if only for a little while. Spend your time here enjoying the quintessential countryside experience without neglecting luxurious touches and timeless style. We love the vintage kitchen, the light painted wooden floors, and the fireplaces in almost every room. All of these details combine to turn this sympathetically restored farmhouse into a warm and cosy home where you can take your time to rest, explore and appreciate the stunning views by the fireside with a glass of red. If heading into town won't shatter the illusion of having travelled back to the 1930s – there are plenty of dining options twenty-five minutes away in Poughkeepsie. You'll find locally sourced seasonal offerings at Farmers and Chefs, farm-fresh...More Details


      • Booked Available
    Hudson Valley FL, House for rent
    House • 6 People • 3 • 3 • pets pool wifi
    From
    $
    2,286 USD /night
    Min Stay 2 nights


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    Hudson Valley FL, USA 

    $ 2,286 USD /Night (minimum stay 2 nights)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    If you’re heading to the Catskills, you want to be fully immersed in the wild greenery. This minimalist home is all glass and clapboard, surrounded by towering trees and secluded from the rest of the world. A wrap-around terrace lets you enjoy the silence of the forest while breathing in the fresh air, and there’s a sustainable garden brimming with vegetables and flowers amidst the pines. The real surprise is the infinity-edge pool and hot tub overlooking the trees, and a boxing gym and games room in the pool house. The architect has done a fantastic job of blurring the lines between nature and the building – it feels like you’re outdoors when you’re inside, thanks to walls of glass. Sleek minimalism is present, with a slate-grey Valcucine kitchen catering for cooks and a simple yet elegant living room set around a fireplace for chilly evenings. Those that enjoy their privacy can bag the garden guest house, which is fully self-contained...More Details


      • Booked Available
    Hudson Valley FL, House for rent
    House • 4 People • 2 • 1 • pets wifi
    From
    $
    354 USD /night
    Min Stay 2 nights


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    Hudson Valley FL, USA 

    $ 354 USD /Night (minimum stay 2 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    Cottontail Creek

    Fill your lungs with the scent of freshly chopped firewood as you step from the crisp Catskills mountain air into this gabled-roofed cottage. Whether you're a couple seeking stolen moments or a group of friends in search of calm, you'll find what you're looking for here. The wood-heady interiors cater to those in love with old-school design, particularly with the vintage wood-burning stove, record player and accompanying vinyl collection. On sunny days, a curl up on the hammock and listen to the babbling brook for hours on end – this simple pleasure is surely a tonic for the soul.Keen hikers will no doubt be drawn to the nearby trails, taking you through the Catskill Mountains with the promise of spectacular vistas along the way. The town of Woodstock, made famous by the iconic 1969 music festival, is just a forty-minute drive away. Here you can load up on supplies and enjoy a hearty meal before heading back to your country retreat. *U...More Details


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    Hudson Valley FL, House for rent
    House • 8 People • 3 • 2 •
    From
    $
    541 USD /night
    Min Stay 2 nights


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    Hudson Valley FL, USA 

    $ 541 USD /Night (minimum stay 2 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    Great Mountain

    Sitting on the deck of this beautiful home in Rosendale, which overlooks the Catskills mountains in one direction and the woods in the other, you'd be forgiven for thinking you're secluded away, miles from civilisation. When in actual fact, Main Street is just down the road. However, the privileged location means that hiking and biking trails start right on your doorstep. After a day exploring the great outdoors, fire up the barbecue for an alfresco meal, or cosy up in front of the wood burner with a book. Inside, the simple, pared-back decor lets the jaw-dropping views take centre stage, with something to catch your eye in every direction. The home is well set-up for kids, with an art/music room, toys, games, books and even a trampoline in the back yard. The lack of TV and occasionally spotty internet connection means the stage is set to unplug from the virtual world and reconnect with the physical one. If you're not ready to let go co...More Details


      • Booked Available
    Hudson Valley FL, House for rent
    House • 6 People • 3 • 2 •
    From
    $
    476 USD /night
    Min Stay 2 nights


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    Hudson Valley FL, USA 

    $ 476 USD /Night (minimum stay 2 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    Make the most of the New York state countryside from this home in Amenia, which is within driving distance of some excellent hikes, such as Macedonia Brook State Park (twenty minutes in the car). It’s also only thirty minutes from the Catamount ski resort, meaning there’s plenty on offer for active guests. Or watch a movie at the drive-in cinema, a two-minute ride away. Back at this home itself, you’ll find a stylish space to return to after a day of exploring the surrounding area. Whether you’re sitting around the fire pit in the yard, lounging on the sofa as a group or enjoying a family meal, the spacious home is ideal for socialising. We love the vintage pieces offering a nod to the area’s agricultural roots. What’s more, there's two laptop-friendly workspaces, making it easy to work from home. *The upstairs bedroom has been built in the eaves, so taller guests may need to stoop in some areas*We recommend having a car to explore all...More Details


      • Booked Available
    Hudson Valley FL, House for rent
    House • 5 People • 3 • 1 •
    From
    $
    881 USD /night
    Min Stay 1 night


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    Hudson Valley FL, USA 

    $ 881 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    The Pond House

    This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home. It was proudly featured in Italy's Icon Design Magazine for its attention to detail and considered use of elegant and characterful materials. We loved the living space, particularly the expansive ceilings, enormous windows and integration of concrete and wood. Rise and shine to picturesque views of the beautiful garden. Relax on the outdoor day bed, which looks out over the legendary Indian Head mountain ridge, have a picnic by the swimming pond, surrounded by juniper trees and century-old cedars, or follow the burbling stream into the woods. Then later, gather around the fire pit. Whatever you decide to do, this home invites you to slow down the pace in style.If you'd like to explore further afield, lace-up your boots and take a drive out to a hiking ...More Details


      • Booked Available
    Hudson Valley FL, Apartment for rent
    Apartment • 6 People • 3 • 3 •
    From
    $
    318 USD /night
    Min Stay 28 nights


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    Hudson Valley FL, USA 

    $ 318 USD /Night (minimum stay 28 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    Unscripted Upstate

    It's guaranteed love from the moment you pull up to this beautiful home in Woodstock. Step through the front door and it's like you've stumbled upon the front cover of a magazine, dramatic wooden stairs juxtaposed with chic upholstery and a light ambience. Every corner of this home has been considered from coffee table books, to Sonos speakers in the living areas, to professional chef's knives and a KitchenAid for cooking. This is a home you'll truly want to live in forever. As for the area itself? Woodstock is the bohemian heart of upstate New York, a hive of local farms, artsy boutiques, and scenic hikes in the Catskills. *There is a minimum 30-night stay here*If you want your four-legged friends to keep you company, pets are welcome at this property *We recommend a car for exploring the Catskills. There is parking outside this home Air ConditioningBathtubBreakfast IncludedCarbon Monoxide DetectorCentral HeatingDishwasherDryerFire E...More Details


      • Booked Available
    Hudson Valley FL, Apartment for rent
    Apartment • 11 People • 4 • 2 •
    From
    $
    1,071 USD /night
    Min Stay 2 nights


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    Hudson Valley FL, USA 

    $ 1,071 USD /Night (minimum stay 2 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    Which Way The River

    Have you ever wanted your very own slice of the Catskills? Of course, you have. Well, here's ten acres of it, to be precise. And it all comes with riverside deckchairs, a six-person hot tub, dense woods, and tubes for floating down the river. It's also safe to say that from this Big Indian Victorian manor, you'll have plenty of stellar hiking and ski resorts within a thirty-minute drive. Not to mention the Peekamoose Restaurant – just one minute away for moments when you don't feel like cooking. Of course, if you want to whip up your own culinary masterpiece, you'll have your enormous kitchen opening onto the outdoor deck, for leisurely riverside dinners too. Your host – a New York-based designer – has crafted the interiors to his idiosyncratic taste, so you'll find that the thoughtful touches such as Moroccan tiles, high-end bedding and paintings by local artists offer an unforgettable experience worth writing home about. So set off on...More Details


      • Booked Available
    Hudson Valley FL, Apartment for rent
    Apartment • 6 People • 3 • 2 •
    From
    $
    811 USD /night
    Min Stay 2 nights


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    Hudson Valley FL, USA 

    $ 811 USD /Night (minimum stay 2 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    Soul Of The Willow

    What at first glance appears to be an abandoned wooden turret lives a secret life as a blissful modern retreat, in this converted willow silo. Nestled amongst the trees ten minutes away from Woodstock, this wondrous three-storey tower is as well positioned to hiking nearby woods and mountains as it is to the galleries and boutiques of Woodstock. Keen skiers will love staying here thanks to its close proximity to the Hunter ski centre, a 30-minute drive away. Discover the hidden lakes and waterfalls nearby by day, and stargaze from your own hammock by night. By the time you leave, you'll be at one with the woods. *The second bedroom has a double sofa bed, rather than a permanent bed*The second and third bedrooms are connected by an adjoining door*If staying here in winter, you may need a 4x4 to get to the silo Air ConditioningBalconyBarbequeBathtubCarbon Monoxide DetectorCentral HeatingChild FriendlyCoffee MakerCooking EssentialsDishwa...More Details


      • Booked Available
    Hudson Valley FL, Apartment for rent
    Apartment • 10 People • 3 • 2 •
    From
    $
    1,151 USD /night
    Min Stay 2 nights


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    Hudson Valley FL, USA 

    $ 1,151 USD /Night (minimum stay 2 nights)
  • Swimming Pool
    Pets Allowed
    WiFi

    Pine's Reach

    It's back to camp at this lakeside home, which has been designed to make the most of its beautiful surroundings. Wooden floorboards, adjoining cabins, folding doors, and outdoor walkways give the sense of being in a giant – and rather quirky – treehouse. First up on your camp agenda will be running wild in the gorgeous grounds. We love the array of activities the spot has on offer, with a barbecue, fire pit, ping pong and foosball tables, kayaks, and a deck to jump straight into the freshwater lake. When you're not exploring the surrounding state parks, the home is full of nooks and crannies to explore. Lounge in the Japanese soaking tub, lie back in an indoor hammock, or watch the sunset from the deck before planning another day of action at this peaceful hideaway. *There are two additional sofa beds available in the master bedroom, and hammocks in the communal areas *During the winter, usually the main house is available to rent - th...More Details


      • Booked Available
    Hudson Valley FL, House for rent
    House • 16 People • 8 • 7 •
    From
    $
    1,817 USD /night
    Min Stay 1 night


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    Hudson Valley FL, USA 

    $ 1,817 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Hudson Grandeur

    This grand, old home in the Hudson Valley feels like a mix between a beautiful Midwest farmhouse and an English manor. A blue clapboard facade and white bannisters suggest country-chic while the pristine white columns at the entrance add the grandeur. It’s set on 1.6 acres of land where you’ll find a resort-style swimming pool and integrated Jacuzzi to rival Palm Springs and terraces shaded by trees for wining and dining outdoors. Inside, we can see why this place has featured in the Wallstreet Journal and Hudson Valley Magazine – the main living room is a vision of class, set around an ornate fireplace and the original tiger oak panelling remains in the entrance hall. The solarium offers a sunny spot to read a book, and the breakfasting room is currently set up as a home office should you need to get some work done. Chefs will be delighted with the beautiful kitchen with its own butler’s pantry and the hand-painted wallpaper in the din...More Details


      • Booked Available
    Hudson Valley FL, Apartment for rent
    Apartment • 10 People • 5 • 3 •
    From
    $
    1,548 USD /night
    Min Stay 1 night


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    Hudson Valley FL, USA 

    $ 1,548 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Surrounded by majestic woodland and meadows, this Salt Point home is filled with the spirit of adventure. It’s the kind of space that transports you to an idyllic retreat – one that is rich in natural beauty. Set within seven acres of sweeping countryside, this is a wonderful place for families and friends to share the magic and wonder of New York State. And from the moment you arrive, you’ll want to savour the lightness and freshness of this home. With views across the garden, the communal spaces are perfect for socialising, relaxing and simply enjoying quality time together. And whether you’re gathering around the table for breakfast or spending cosy nights by the fire pit, this is a lovely setting to celebrate life’s special moments.Days can be spent relaxing by the pool or hiking through the surrounding woodland, while the historic town of Rhinebeck and the village of Millbrook are only a twenty–minute drive away. *There is free pa...More Details


      • Booked Available
    Hudson Valley FL, Apartment for rent
    Apartment • 6 People • 3 • 3 •
    From
    $
    479 USD /night
    Min Stay 1 night


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    Hudson Valley FL, USA 

    $ 479 USD /Night (minimum stay 1 night)
  • Pets Allowed
    Air Conditioning
    WiFi

    The Gallery Wall

    Art lovers, rejoice – this retreat between Beacon and Fishkill is for you. The homely space is a work of taste, elegance and impeccable interior design, with contemporary furnishings complemented by the owner's impressive art collection. Let us paint a picture: you wake up with a woodland vista visible through floor-to-ceiling windows, prepare fresh coffee in the sleek subway-tiled kitchen and lounge on the L-shaped sofa while you fully wake up. The atmosphere is calming, and the day feels like a blank canvas. On the wrap-around deck, you can listen to the breeze rustling the trees and the gentle birdsong of your only neighbours. Experience a renaissance of self-care at this home, whether soaking in the deep free-standing tub or having a potter around art galleries in the nearby town of Beacon – just a nine-minute drive away. The village of Fishkill is also within easy reach, where you can enjoy meals out and pick up any necessities you...More Details


      • Booked Available
    Hudson Valley FL, Apartment for rent
    Apartment • 8 People • 4 • 2 •
    From
    $
    725 USD /night
    Min Stay 2 nights


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    Hudson Valley FL, USA 

    $ 725 USD /Night (minimum stay 2 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    The Dutch Farmhouse

    Set between the Hudson River and the Catskill Mountains, this spectacular 18th-century farmhouse is full of upstate New York charm. Nestled in 35 acres of secluded woodland, the house is a breath of fresh air less than two hours’ drive from the hustle and bustle of Manhattan. Step inside and you will instantly notice the owners’ keen aesthetic eye and attention to detail. Each room is bursting with character, and full of antique furniture, contemporary art, and vintage trinkets. The distinctive living room has a large wood burning fireplace and plenty of games for the kids. There is also a sun room which is perfect for relaxing in with a book. The farmhouse kitchen is well equipped with a range of appliances and cooking essentials. Upstairs, the palatial main suite comes with an office for remote working, a living area with its own fireplace and coffee station, and a claw-footed bathtub in the bathroom. The second and third bedroom hav...More Details


      • Booked Available
    Hudson Valley FL, Cottage for rent
    Cottage • 6 People • 3 • 1 •
    From
    $
    421 USD /night
    Min Stay 2 nights


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    Hudson Valley FL, USA 

    $ 421 USD /Night (minimum stay 2 nights)
  • Pets Allowed
    WiFi

    The Mountain Glow

    Immersed in a sanctuary of trees, this rustic cabin invites you to enjoy a serene retreat in the Catskill Mountains. Set across five acres and just a six-minute drive from the charming town of Roscoe, there’s everything you could need to feel inspired and renewed by the majestic beauty of this special environment. From the atmospheric views to the exceptional styling, every detail has been considered to fill your stay with freedom and ease. And from the moment of arrival, you’ll want to pause and savour the calming simplicity of this space. High ceilings and large windows create a wonderful sense of lightness, while the seamless blend of natural tones reflects the beauty of the surroundings. Step outside and you’ll discover the expansive deck is ideally positioned for a quiet morning coffee, or later with magical evening drinks and stargazing by the welcoming fire pit. Follow the mountain road and you’ll find the bustling town of Living...More Details


      • Booked Available
    Hudson Valley FL, House for rent
    House • 8 People • 4 • 5 •
    From
    $
    1,244 USD /night
    Min Stay 2 nights


    View Details

    Hudson Valley FL, USA 

    $ 1,244 USD /Night (minimum stay 2 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    High Tea - Hedgerows

    This home sits pretty as an English manor in the countryside of upstate New York, a ten-minute drive from the picturesque town of Pawling. Grecian-style columns greet you on arrival and the striking white facade glows against the verdant green gardens – it sits on 18 acres of land. The gardens are studded with ancient oak trees between perfectly manicured lawns and those that enjoy their privacy can opt to stay in the separate cottage in the grounds.Dating back to 1840, the interior is an homage to elegance and eloquence. The main lounge, with its big Georgian windows and grand piano, looks out over the gardens. Then there are two further living areas – the garden room with a traditional old fireplace and a library lined with towering bookcases. The kitchen looks as though scullery maids still bustle through, with its hanging pots and farmhouse charm. Though all the appliances are state-of-the-art modern. The huge dining room features a...More Details


      • Booked Available
    Hudson Valley FL, Apartment for rent
    Apartment • 6 People • 3 • 1 •
    From
    $
    379 USD /night
    Min Stay 1 night


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    Hudson Valley FL, USA 

    $ 379 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    The Foggy Falls

    Based in a leafy spot in the peaceful village of Highland Falls, this idyllic and quintessentially American holiday home is waiting with open arms to welcome you on your holiday to the North East of the USA. Highland Falls is a cosy community on the bank of the Hudson, close to West Point and its fascinating museum, and also near lots of beautiful outdoor spots that make the state of New York so sought-after by those looking to be impressed by Mother Nature.We love the modern feel of this home, with stylish furniture, cool lighting and trendy soft furnishings that make it feel contemporary. The large lounge area is great for spending family time together while you watch a movie on the big screen, and the dining area makes a wonderful place for feasting on burgers and hot dogs before spending the evening sipping beers and playing card games. No need to leave the pooch at home when you stay here too, as dogs are welcome to join you for yo...More Details


      • Booked Available
    Hudson Valley FL, House for rent
    House • 6 People • 3 • 2 •
    From
    $
    617 USD /night
    Min Stay 2 nights


    View Details

    Hudson Valley FL, USA 

    $ 617 USD /Night (minimum stay 2 nights)
  • Pets Allowed
    Air Conditioning
    WiFi

    Rust - Stars

    Featured in both Dwell and the New York Times, we couldn't help but be impressed by this cabin, standing on 19 acres of private land. The reason for the media attention will be evident in the open living space. Perfect for socialising with your guests, the wooden furniture and beams overhead capture the frontier spirit – turn on the woodstove and play games, or make use of the projector. The bedrooms are small but comfortable and kids will love the bunk beds. Of course, the real draw here is the outdoor area – acres of private, forested land, a private pond (perfect for spotting wildlife), tree swings and fire pits collude to create a rustic paradise. *The bunk beds are only suitable for children under 12, so a maximum of four adults and two children are allowed here. The bedrooms are small with limited storage space.*Your host provides a free Pack 'N Play on request. Due to the unfenced pond and forests, children must be supervised at...More Details


      • Booked Available
    Hudson Valley FL, Apartment for rent
    Apartment • 10 People • 4 • 2 •
    From
    $
    741 USD /night
    Min Stay 1 night


    View Details

    Hudson Valley FL, USA 

    $ 741 USD /Night (minimum stay 1 night)
  • Pets Allowed
    Air Conditioning
    WiFi

    Natural Calm

    For those in search of a rustic retreat filled with the warmth and charm of country living, this cabin-inspired home welcomes you to put down your bags, and experience its range of comforting features. From lazy afternoons by the fire to long soaks in the jacuzzi bath and magical evenings gathered around the table, every detail of this setting inspires a wonderful sense of relaxation. And with two living rooms, a fully equipped kitchen and four bedrooms, you’ll find an abundance of space to unwind and enjoy quality time together. Days can be spent embracing the great outdoors with long hikes or exploring the little town of Monroe (just a five-minute drive away). From cosy cafes and restaurants to grocery stores and museums, you’ll find everything you could need for a fulfilling stay. Wherever the day takes you, this home provides the perfect setting for fun-filled barbecue meals, and heartwarming evenings cuddled up around the roaring...More Details


      • Booked Available
    Hudson Valley FL, Apartment for rent
    Apartment • 16 People • 8 • 4 •
    From
    $
    3,621 USD /night
    Min Stay 1 night


    View Details

    Hudson Valley FL, USA 

    $ 3,621 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    The Picket Fence

    Found on 11 acres of verdant green land, this home might seem like a typical American house with its New York-style architecture, but what it represents is rest, relaxation and just the right amount of seclusion. It might only take an hour to get into the heart of New York, but the sheer size of this property ensures that it’s as peaceful as you make it. Take scenic strolls around the garden, thermos in hand, until you find the perfect spot for a picnic. From the porch, you can admire the rolling hills and on the balcony or porch swing, you can nurse a cup of coffee with a proper dose of contemplation. The swimming pool with its cool, welcoming waters is perfect for bright sunshine days, but don’t be surprised if the little ones want to spend every waking minute taking the custom slide into the water. The cinema room is ideal for family movie night but can also be turned into a home bar after the little ones go to bed. Ideally, you’d wa...More Details


      • Booked Available
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