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    Found 29 Hudson Valley Fl holiday homes for rent

    Cottage • 10 People • 4 3 pets pool wifi
    From
    $
    4,758 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 4,758 USD /Night (minimum stay 1 night)
  • 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
    House • 20 People • 8 10 pool wifi
    From
    $
    2,953 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 2,953 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Rise with the Sun


    Nestled within 26 acres of beautiful grounds, this private estate welcomes you to an immersive retreat in Rhinebeck. From the indoor sauna and hot tub to the calm rooms, every detail has been considered to inspire optimum relaxation. There is also a yoga and fitness studio as well as a pool table and a wet bar – ensuring entertainment options for the whole group. Remote workers will appreciate the dedicated desk space, while we imagine everyone will love gathering by the fire for games or movie nights. From here, you can follow hiking trails straight from the door and it’s less than a fifteen-minute drive to Hyde Park and Rhinebeck. *There is free private parking for up to ten cars here. *Please note this home is spread across two floors with two bedrooms located on the ground floor. *You won't find a welcome hamper here, so we'd recommend packing some bits and bobs to get you started. *Hen and stag parties are strictly not allowed a...More Details


    • Booked Available
    House • 16 People • 8 7 pets pool wifi
    From
    $
    1,476 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 1,476 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
    Apartment • 10 People • 3 2 pets pool wifi
    From
    $
    1,393 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 1,393 USD /Night (minimum stay 1 night)
  • 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 -...More Details


    • Booked Available
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    House • 6 People • 4 1 pool wifi
    From
    $
    1,378 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 1,378 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    A New Perspective


    On the bank of the Hudson river lies A New Pespective. Designed by renowned architect Philip Johnson in the late 20th Century, attention has been paid to every element of the architecture here. You'll enjoy mornings as the light streams into the house just as much as you'll enjoy the golden evenings sipping drinks and taking in the panoramic views. With everything the Hudson Valley has to offer right on your doorstep, you'll spend your days exploring waterfalls and trails before returning home to relax in style. *A car is recommended to make the most of the surrounding area Air Conditioning Balcony Barbeque Bathtub Blender Board Games Carbon Monoxide Detector Central Heating Cleaning Products Cooking Essentials Dishwasher Dryer Drying Rack Exercise Equipment Extra Pillows and Blankets Fire Extinguisher Fireplace First Aid Kit Free Parking On Premises Freezer Fridge Garden Gym Hair Dryer Hangers Iron Ironing Board Kettle Kitchen Kit...More Details


    • Booked Available
    House • 8 People • 4 5
    From
    $
    1,271 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 1,271 USD /Night (minimum stay 1 night)
  • 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...More Details


    • Booked Available
    House • 6 People • 3 3
    From
    $
    1,165 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 1,165 USD /Night (minimum stay 1 night)
  • Pets Allowed
    Air Conditioning
    WiFi

    This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods. Floor-to-ceiling windows make full use of the region’s scenery, and sliding doors out onto a deck mean you can practically reach out and touch the pines – you can even listen to the rushing waters of the creek from here. Modern and stylish, the design here isn't trying to outshine the views, with wood floors, white walls and a Scandi feel to its furnishings. Two of the bedrooms are on the top floor and have such great views across the canopy you'll think you're staying in a treehouse, while immaculate bathrooms are outfitted with marble, lava stone and Italian Porcelanosa tiles. If you can drag yourself away, head out on hikes, explore the nearby farm shops, or book a meal at a...More Details


    • Booked Available
    Apartment • 8 People • 4 2
    From
    $
    1,067 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 1,067 USD /Night (minimum stay 1 night)
  • 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 ha...More Details


    • Booked Available
    Cottage • 9 People • 4 3
    From
    $
    1,047 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 1,047 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    The Archway


    Urbanites looking for a tranquil getaway will enjoy the large indoor and outdoor spaces to relax and unwind. Each room has been lovingly styled by the host, Ayanna, who has instilled her character and charm into the home. The location has a semi-rural feel, which is wonderfully peaceful, but The Archway is still located near to the village centre. The home is well suited for families as there's lots of room for children to play and the twin bedroom has been thoughtfully designed to welcome young ones. * There is no access to the garage, there is however plenty of space to park on the driveway * It works perfectly smoothly, but the kitchen isn’t enormous Air Conditioning Baby Bath Baby Monitor Balcony / Patio Barbeque Bathtub Beach Essentials Bicycles Black-Out Blinds Blender Board Games Buzzer / Wireless Intercom Carbon Monoxide Detector Central Heating Cleaning Products Coffee Maker Cooking Essentials Cot / Crib Dishwasher Dryer Dr...More Details


    • Booked Available
    House • 6 People • 3 3
    From
    $
    945 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 945 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Air Conditioning
    WiFi

    Sweetwater Hideaway


    Sweetwater Hideaway is a magnificently organic cabin nestled in the forestry Woodstock landscape. The timber vaulted ceiling, exposed wooden beams and deep chestnut finishings create a grand interior. Inviting sofas set around a stone-walled fireplace and a quaint library nook add a homely, cosy element to the house that is furthered by the wonderfully rustic kitchen. Simple, elegant bedrooms have plush beds and plentiful dressing room, including one organically-inspired room and a bright, colorful dedicated children’s room. There are luxurious bathrooms that have exquisitely tiled walk-in showers and soaking tubs. The cabin is nestled into the beautiful natural outdoors, while also being near enough to Woodstock to wander through legendary town. Just take a short drive to the town centre to explore all the shops and restaurants there are, or perhaps head to the Overlook Mountain Trailhead for a wholesome day of hiking. * The pool is ...More Details


    • Booked Available
    House • 5 People • 3 1
    From
    $
    823 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 823 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 hik...More Details


    • Booked Available
    Apartment • 11 People • 4 2
    From
    $
    706 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 706 USD /Night (minimum stay 1 night)
  • 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
    House • 6 People • 3 2
    From
    $
    703 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 703 USD /Night (minimum stay 1 night)
  • Swimming Pool
    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 ...More Details


    • Booked Available
    Apartment • 6 People • 3 2
    From
    $
    660 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 660 USD /Night (minimum stay 1 night)
  • 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 Conditioning Balcony Barbeque Bathtub Blender Board Games Carbon Monoxide Detector Central Heating Child Friendly Clean...More Details


    • Booked Available
    House • 8 People • 4 3
    From
    $
    653 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 653 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    WiFi

    Doric Detail


    Originally built in the 1870s, this farmhouse has been added to over time to create a sociable family home. Inside, original details such as exposed wooden beams and large sash windows are complemented by vintage furniture and traditional furnishings, while a bar is ideal for evening cocktails. But you’re likely to spend most of your time outside, exploring the ten acres of land, enjoying a drink outside on the deck, taking some time to reflect at the koi pond, or gathering around the outdoor fireplace after the sun goes down. There’s also a natural pool fed by a mountain stream, which you can swim in, surrounded by frogs, water lilies and other aquatic life. * The home is spread over numerous levels, so it is not wheelchair friendly * The pool is natural, so while you can swim in it, you will share the mountain water with aquatic life * Children should be supervised around the pool and pond Barbeque Bathtub Blender Carbon Monoxide ...More Details


    • Booked Available
    House • 10 People • 5 3
    From
    $
    645 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 645 USD /Night (minimum stay 1 night)
  • Pets Allowed
    Air Conditioning
    WiFi

    Dahlia Darling


    Indulge yourself in the natural world at this sun-drenched home, with plenty of space for friends and family indoors and out. You'll find toys and games along with free children's sledges for enjoying the snow, and kids will love the bunk beds. The outdoor fire pit offers cosy evenings under the stars, and the babbling brook at the end of the 5-acre garden brings you that bit closer to nature. Just minutes away you'll find Bethel Woods, the home of the original Woodstock, and the town of Bethel along with the picturesque Lake Superior State Park are an easy drive away. *There is space to park for free outside this home. Due to its location, we recommend hiring a car here. *There is a loft over the living room for overflow guests with two single mattresses on the floor – these aren't suitable for unsupervised children under 14 due to the low ceilings, and are accessed via a ladder. *Your host can provide a high chair and two children's...More Details


    • Booked Available
    Apartment • 6 People • 4 3
    From
    $
    590 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 590 USD /Night (minimum stay 1 night)
  • Swimming Pool
    Pets Allowed
    Air Conditioning
    WiFi

    Art - Nature


    This home's architecture, interiors and colourful prints all share a mid-century modern style, but its woodland surroundings are more Hansel and Gretel than Gilbert and George. In a tiny hamlet in upstate New York, it’s surrounded by mountains, lakes and forest – great for skiers, hikers and wild swimmers alike. The home has several standout features but we love the double-height living area, with its huge windows and cosy fireplace. The galleried landing has a desk in case you need to keep one eye on work while you're away, and the huge deck has a gas barbecue for those long lazy lunches outdoors. While its statement design pieces add interest, it's a homely place too, with a bedroom set up for children, logs provided for the fire, and plenty of books to pick through on the shelves. Just minutes from a choice of state parks, forests, orchards, and wineries, your days will be filled with outdoor adventures – and all just an easy drive f...More Details


    • Booked Available
    House • 8 People • 3 2
    From
    $
    569 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 569 USD /Night (minimum stay 1 night)
  • 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
    House • 6 People • 3 2
    From
    $
    491 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 491 USD /Night (minimum stay 1 night)
  • 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 a...More Details


    • Booked Available
    House • 4 People • 2 1
    From
    $
    490 USD /night
    Min Stay 1 night

    Hudson Valley FL, USA 

    $ 490 USD /Night (minimum stay 1 night)
  • Pets Allowed
    Air Conditioning
    WiFi

    The Ashokan


    The Ashokan is an exquisite barn-styled house nestled within rich woodland landscape. The quaint exterior shelters an incredibly contemporary and stylish interior. From the patterned floors and wonderful impressionist paintings, to the rustic oak furnishings and floorboards, this house seamlessly blends homeliness with elegance. The large bedrooms have plush deluxe beds (although the mezzanine bedroom offers very little privacy and has no curtains), as well as plentiful dressing space and luxurious bathrooms. The estate is located moments away from the beautiful Ashokan reservoir. Spend your days taking in the breathtaking landscape while hiking the trails, or perhaps head into the nearby Woodstock to wander around the legendary town. * The house is fairly remote and a car would be useful to get around * Be prepared to share as there is only one bathroom *Bedroom two is on a mezzanine level – there is little privacy with the open-plan...More Details


    • Booked Available
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