Vacation Home Rentals By Owner In Woodstock, NY

$410.67

Serene Woodstock 3 bedroom cottage with sweeping mountain views

Woodstock, New York, United States

Recently built 3 bedroom/2 bath house with mountain views on 5 beautiful secluded acres surrounded by trees, a quick 3 minute drive to the center of town. Fantastic in all seasons and close to amazing Catskill hikes, skiing, sledding, waterfalls, and the Hudson River, as well as the towns of Phoenicia, Saugerties, Kingston, Catskill, Hudson, Rhinebeck, and Tivoli.brbrFollow us on Instagram! @ohayowoodstockbrbrThe space:brbrWhile looking for a small, move-in-ready cottage in Woodstock we fell in love with this beautiful piece of land with views of Overlook Mountain — despite the fact that the existing house was falling to the ground, unoccupied for years.brbrWe decided to change course from our original plan and build a new house from the ground up, which has been an exhilarating adventure. Our goal was to build a comfortable, Byrdcliffe-meets-Scandinavia getaway for our family and friends, and we sometimes rent it when we are not able to be here to enjoy it ourselves.brbrThe house has a spacious kitchen with all the amenities, large dining table, kitchen bar, comfortable living room with record player and lots of vinyl, and an upstairs library with comfy couch and tv. Outside we have a hammock, fire pit, Adirondack chairs, covered front porch, and large sunny patio with table and umbrella. The house is super cozy in cold weather and breezy in the summer months.brbrGuest access:brbrOur guests have access to the entire house, private driveway, patio, and 5 gorgeous acres.brbrInteraction with guestsbrbrOur property manager is available by text/phone for any help you may need, and lives nearby in case of emergency.brbrOperating Permit #22H-186 Woodstock, NY

3

Bed

2

Bath

5

Sleeps

$567.8

/ Nightly

Private Vacation Home

Cozy Escape in Woodstock

Woodstock, New York, United States

Summary:brFind complete country zen within walking distance of the village of Woodstock. This charming 3-bedroom has all the essentials for time spent upstate: a grassy yard with an old growth tree, porch rockers, and even a private library.brbrEvery season here has its moments of magic, from winter snow to summer fireflies. Bring a group and enjoy spacious living areas and a full kitchen, plus easy access to everything from dining to concerts to outdoor recreation including hiking, skiing, and swimming.brbrThe Space:brMidcentury modern touches add a splash of chic to an otherwise perfectly quaint getaway. Enjoy all the comforts, including heat and A/C as well as a washer and dryer.brbrbrA YARD OF YOUR OWNbrbrGet ready for lazy days spent relaxing in the yard. Nothing says summertime quite like a barefoot afternoon picnic here. Visit during the fall months for a vivid display of colors, winter for whisper-quiet snow scenes, and spring to see the 150-year-old hydrangea tree burst into bloom. Gather around the fire pit or sit back in the hot tub to watch the day fade into star-studded night.brbrBring a cold pitcher of lemonade or a warm mug of cocoa out to the covered porch and settle into a rocking chair. We guarantee it’ll be your favorite spot to watch fireflies glowing at dusk, autumn leaves falling in the wind, or winter birds landing in the snow.brbrA PLACE FOR EVERYONEbrbrSun-dappled and fully stocked, the kitchen is just as suited for whipping up meals as it is for lingering over morning coffee. Here, you’ll find a full suite of appliances as well as a quaint dining nook overlooking the yard.brbrAsk us about our favorite nearby markets for delicious local ingredients—you’ll want to save at least one night for a homemade feast served in the candlelit dining area.brbrAn open floor plan means that everyone can be a part of the same moment. You can cozy up on the living room sofa to gaze out over the yard or catch a movie on the flat-screen TV without losing touch with those still chatting in the dining area.brbrBut when quiet is what you crave, the library is the answer: pull a book from the shelf and sink into the sofa for some solitary bliss. Many say it’s the best spot in the house—we’ll let you decide whether to let your fellow guests in on the secret.brbrWHERE DREAMS HAPPENbrbrThe best days spent in the mountains are those fueled by a good night’s sleep, so we’ve designed our bedrooms to be restful to the core. Our home features:brbr- Master bedroom suite with king-size bed, flat-screen TV, and en-suite bath with shower/tub combinationbrbr- Second bedroom with a full-size bed and easy access to a newly renovated shared bath with shower/tub combinationbrbr- Converted sleeping space in the library with a pull-out sofa with upgraded memory foam mattress and en-suite bath with shower, and, of course, a nearly endless source of bedtime storiesbrbrOperating Permit # 21N-204 - Woodstock NYbrbrGuest Access:brYour code to enter will be shared with you before check in. Upon your arrival - go through the screened porch entrance and enter your code into the keypad and your in!brbrThe Neighborhood:brWe live in a great spot. We are within walking distance to town but almost at the end of a quiet dead end road.brbrGetting Around:brWOODED SETTING, VILLAGE CHARMbrbrWalk one mile to the village of Woodstock to find a thriving dining scene, boutiques ranging from psychedelic to modern chic, and theaters and venues for concerts, shows, and more. Even in the age of Covid, the village is thriving with socially distanced revelry.brbrBring your boots and get ready to explore miles upon miles of hiking trails. Bring the whole family for a woodland stroll, or see how many 3,500’+ peaks you can check off your list—there’s 35 of them in the Catskills region.brbrNearby Hunter and Bellayre resorts offer skiing in the wintertime and lake swimming or festivals in the spring, summer, and fall. Spend an afternoon tubing down the Esopus and finish the day with a stop in the village of Phoenicia, or head to the city of Kingston for even more dining and cultural options.brbrInteraction with Guests:brWhen you confirm your booking we will send you all of the info you need for the home. If you need anything just message us or email us and we can be sure to take care of you right away.

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Bath

Sleeps

$722.38

/ Nightly

Private Vacation Home

Woodstock historic artist estate - The Pond House

Woodstock, New York, United States

This is an architect/artist home featured in various design magazines including Architectural Digest and Icon Design Magazine Italy. GQ magazine rated the Pond House amongst the 7 best vacation rentals in the US. In short walking distance to the center of Woodstock the secluded setting with a surrounding pond and private waterfall bordering public preserves, as well as the attention to architectural detail, is unique.brbrThe Pond House is the 1930s original Reginald Marsh artist studio building with 16' ceiling height and tall artist windows. Frederick Dana Marsh, father of the well known Social Realist painter Reginald Marsh, married Mabel Van Alstyne in 1930, starting a notable artistic partnership as the Van Alstyne Marsh Collection that was later acquired by the Smithsonian Institution. Their home was unique for Woodstock —'It was in the background of the Mona Lisa; a Van Gogh landscape; a train ride through Tuscany, ball shaped junipers; a pond that bracketed the house; expansive lawns; a gathering of birches. But most of all, big cone shaped cedar trees. It is a marvelous thing to look up at backlit clouds at sunset, see the intrusion of cedar peaks, pointing up like soft missiles and the erratic flight of mosquito catcher bats making ninety degree turns down the channels between the trees. A photographer friend was here last weekend, “Don't worry about framing the picture, just point and shoot. The landscaper framed it for you hundred years ago. ' Here we quote Austin Metze, a long time Woodstock writer. brbrToday the former artist studio of the estate is an architect-renovated gem featuring elevated design standards that include architectural details, high vaulted ceilings, original art work, a hand-selected library, a piano, a wood burning stove. The contemporary kitchen is fully equipped with premium appliances and amenities. The house comes with central A/C and radiant floor heat. The floor plan is open, which is ideal for a family, but not ideal for guests seeking privacy from each other.brIt’s a socially enhancing and creative space, from the bedrooms to the open dining/living room, gardens and terraces with an outdoor charcoal grill, outdoor dining and lounge areas.brbrThere are 2 bedrooms and a kids room, the master bedroom is offering an especially tranquil overlook of the pond under the stars, with floor to ceiling windows on three sides without obstructing shades. It is open to the staircase with the kids room adjacent. The kids room with a twin-sized bed can only be accessed through the master bedroom. The queen-size bedroom is next to the bathroom downstairs, adjacent to the pond with a glass facade and sliding doors to the staircase and bathroom. It's a very special room, with deer walking by the glass facade a few feet from the bed. There are no neighbors on that side of the house, hence the glass facade in both bedrooms and bathroom need no coverings. brbrPond and Carriage House are separated by the owner-occupied adjacent Manor House, facing away from each other ensuring privacy. No other house is visible from inside the Pond House with its own designated back yard facing the pond and the stream. The grounds and pond surrounding the Pond House are reserved for the Pond House. The Pond House feels very secluded, since two sides of the property are bordering preserves. The pond is not a swimming pond, but the stream comes with multiple swim holes and a waterfall. The swim hole with outcroppings and waterfall is shared with the Carriage and Manor House, with other swim holes a short stroll through the woods away. An outdoor day-bed overviews the legendary Indian Head mountain ridge. The parking area comes with an electric car port.brbrWoodstock is an historically aspirational location with a variety of farm-to- table restaurants, eclectic bars and artisan shops. Upon request we offer professional resources from childcare and house keeping services to a private chef and a massage therapist. The estate is a within a 40 minute driving distance to major New York skiing destinations Belleayre Mountain, Hunter Mountain and Windham Mountain.

Bed

Bath

Sleeps

$272.52

/ Nightly

Private Vacation Home

Woodstock Paradise with Gardens / Private Heated Pool--& Cozy Winter Wonderland

Woodstock, New York, United States

Our cozy art-filled home is nestled in the Woodstock forest with an acre of perennial gardens and private swimming pool. It is also a snug winter retreat for a single or couple (possibly an additional small child).brbrThe charming and comfortable cottage-like home we have remodeled out of a well-built 1950s Swedish-style country home is perfect for couples sharing a lovely king-size bed, singles seeking a get-away, or couples-plus-1 (extra fee for use of our twin-size sleep space--babies in portable cribs stay free!). The main bedroom has an excellent king mattress with white organic cotton sheets. The simple windows have French lace coverings for privacy.brbrThis is an open house with beautiful wood floors / hand placed ceramic tiles in bathroom and kitchen, with skylights, bay windows, and a beautiful vintage claw-foot tub for long soaks (a shower head also provided). It also has a gorgeous upright piano. Musicians and artists have loved our space. brbrOur space is located inside the village of Woodstock, only 10-minute walk to the Village Green (or 3 min drive). In season, our swimming pool is surrounded by forest and gardens open for summer guests (heating available per your request). Our indoor space is a charming private home including French antiques as well as the piano, with an inset fireplace for winter-spring and fall evenings. Private drive to house in forest makes this extra tranquil as you don't see or hear a road, although we are so accessible to the quaint Woodstock village with its bars, restaurants and food markets. Fountains, flowers, and birds help enjoy the special perennial gardens spring through fall. The deer will come wandering through...and you hear the birds everywhere in and outside the house. br brQuiet and peaceful, yet close to Woodstock town businesses like chic boutiques, and some wonderful restaurants, our location offers the best of both worlds. A perfect space for artists and couples or close friends seeking a restful vacation. And everyone loves the pool in season! brbrWe are also pet friendly -- one small or medium size dog (or cat) allowed per stay. brbrEnticing decks with various garden seating and views of garden and forest. Barbecue under the stars--or use one of our garden fire-pits. brbrA front bay window full of plants faces a front deck. brbrFor colder nights, we have a living room bluestone fireplace (now a smoke free inset with sealed glass door provides lovely wood heat). House has great winter lighting and ample shade in summer. brbrAC in summer is available (additional fee--just let us know your needs). The house also stays cool as it is covered by shade trees in summer. (In winter, the sunlight comes through south-facing bay window for added natural warmth. Regular oil-furnace heat is also available for winter as well as inset-fireplace, which operates like a wood stove but looks like a fireplace with gorgeous bluestone work. brbrBeautiful screened windows as well as sliding door open out to private back deck with forest views all around. brbrCook delicious meals in our simple but fully equipped kitchen with granite counters and Spanish tile floors--or use the barbecue on the deck in the warm season. Enjoy nights of stargazing while eating at the outdoor table with chairs and lounges. There is also an antique French dining table indoors that pulls open with antique chairs. brbrOur 30-foot pool is excellent for swimming or just bobbing, and is surrounded by the forest and a special pool garden with blooming perennials including a magnificent rose bush, and colorful wildflowers. We offer sun umbrellas and chairs for lounging around the pool and in other outdoor seating spots. There's also a hammock for your use.brbrFor a change of pace, can also take a 5 minute walk down the road to the Woodstock Millstream swim hole for a refreshing cool dip on hot summer days, or visit one of our other local stream swim holes (just ask for info!)brbrConsider taking a walk in the woods following the Town of Woodstock paths through the Comeau Property forests along the Millstream. It takes 5 min. to drive to the trailhead. These rambles are refreshing and joyful. Dogs must be on leash!brbrThis is our real weekend home, developed over 30 years of love and care. We are writers and professors who love books, art, writing, and the quiet of our special house. Come enjoy our books, French antiques, and artwork. We love to share it with others when we ourselves are traveling. Come and enjoy our soothing, magical, tranquil atmosphere. Our space is the perfect retreat for one to three people.brbrMusicians can play our lovely piano. Cooks can make magical meals to serve on our antique French table or, in good weather, out on the deck. brbrOr take a stroll into the heart of the Woodstock village very close by to shop or eat great food. Hear music in local venues for the cost of a drink in places like the Colony (restored 19th century hotel made into a music venue) right in town. We can give more information about live music venues, such as the renown Ramble, the Bearsville theater down the road, or the Station Bar. Woodstock is a town of music! brbrWe provide a full Woodstock House Manual for your stay, with local venue tips. And just ask for information -- we can recommend our favorite current restaurants and local hang-out spots. The gardens also have art and mobile sculptures by our renown family artists. (All information in the Manual hardcopy.) You may not even want to leave the Gardens! They are fabulous in summer/early fall. You even have fresh herbs available there for cooking. brbrDon't miss this opportunity to relax by the pool, on the decks surrounded by flowers and greenery, with sumptuous views of the forest when our calendar allows. We do think this is a PARADISE. IOur guests over the years tell us how peaceful and relaxing our place is, and that the photos often don't do the place justice. brbr***brbrMore detailed information: brbrPolished wood floors are laid with authentic Persian carpets (sometimes removed in summer months), Our calm living room opens up to skylights and a bay window. Relaxing chairs and rockers are located multiple parts of the house. brbrThe bathroom is charming and simple, with a large claw tub (no standup shower but we provide a shower head in our antique tub). Our equally simple kitchen has authentic Italian tile floors and granite counters, but is fully equipped for real cooking (basic appliances and herbs etc available for use).brbrEnjoy our superb classical / jazz CD collection, as well as turntable for historic vinyls (organized in living room closet). brbrThe house has private safe parking, and is located on a private drive off a low-traffic road. brbrWe are licensed by the town of Woodstock Permit #20H-172. We follow all town, county, and state laws for short term rentals.brbrWe are animal lovers. One pet can be allowed during your stay (ONE well-trained dog or cat). Please let us know. Note that dogs when outside must be on leash to protect local property owners. There are also sound ordinances we can point you to. No parties or loud noises, due to local laws protecting Woodstock neighborhoods. brbr***brWe hope you will be our guest!

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Bath

Sleeps

$461.07

/ Nightly

Private Vacation Home

Blissful Retreat Elegant , Charming & Peaceful

Woodstock, New York, United States

Permit # 20H-095brBrand new, stylish, elegant, 1 bedroom apartment with office above a garage, located on 10.5 acres and a 3 minute drive from Woodstock.brFully equipped kitchen, cozy lounge room with fireplace, beautiful bathroom, vaulted ceilings with weathered wood beams, antique doors with glass knobs and antique chandeliers create an ambience of old and new world charm.brThe apartment is located in a separate building from the main house where the owner lives with their lovable labradoodle Buddy. Great quiet location.brbrThe owners wanted to create a space that was warm & comfortable with a touch of rustic, old world charm. The weathered beams , chandeliers, old doors with crystal knobs combine the old and new charm and elegance to every room. A full kitchen has everything one needs to cook a gourmet meal with pots & pans, platters, drip coffee machine & french press coffee maker, nutri bullet, wine refrigerator, GE CAFE series gas range & a large GE fridge .brbrThe quartz countertops & the kitchen island create an exceptional kitchen space where you can sit and enjoy mountain views out the kitchen window while sipping your morning coffee.brbrThe Master bedroom hosts a Queen sized bed, with storage room for luggage and hanging space . The office has a desk 3 large storage cupboards for luggage and hanging space and living room has additional pull out couch.brbrThe bathroom has a European feel with Spanish ceramic tile , and a rain shower with glass enclosure. The vanity provides lots of drawers and cupboards for toiletries . There is also weathered beam shelving which provides additional storage space in the bathroom. There is an old school house window feature in the bathroom to create light.brbrThere are weathered beams throughout the vaulted ceilings in every room & the chandeliers bring a sense of elegance and chic to the space.brbrThe fireplace is the focal point of the lounge room & creates a cozy ambience. There is a 55 inch TV that you can logon to your streaming platforms.brbrAll lighting is dimmable throughout the apartment and every room has a very efficient AC/ heating system for your comfort depending on the season.brDownstairs on the first floor there is a full laundry room/ mudroom where you can leave your jackets, shoes and ski gear.brbrThe deck is very private from the main house and overlooks the woods. One has a sense of being in the treetops.You can dine at the outdoor table and chairs on the deck and soak up the sun on the chaise lounges, while reading a book or taking a nap.brbrThere is a washer/ dryer located on the first floor for your convenience during your stay. You can close the door to reduce the noise.

Bed

Bath

Sleeps

$454.53

/ Nightly

Private Vacation Home

Woodstock Mid-Century Gem in the Woods - Secluded Getaway Close to Town

Woodstock, New York, United States

You will have total privacy and safety on four wooded acres, 1.1 miles from the Woodstock village green. Enjoy the eclectically-decorated three bedrooms, large living room, separate dining room with cathedral ceiling and sunken seating area and 1.5 baths. Period 1960 s galley kitchen features updated appliances and new cook s stove. Also includes full laundry, Smart TVs with premium cable in LR and master BR and high-speed WIFI throughout. Recently added: vinyl listening station with 50+ classic rock and folk LP's and vintage stereo system.brbrYou can't do any better in Woodstock than the historic Byrdcliffe Arts Colony, and you can't get any closer to the colony than this home, built in 1968 and still brimming with authentic mid-century charm and a musical history. As you approach the house on the stream-side private road, you'll immediately know you have arrived someplace special. It's surrounded by woods for ample privacy, but there is plenty of open and sunny outdoor living space as well. The main living room features a large sectional sofa and a Roku Smart TV with full premium cable, high-speed WIFI, vinyl listening station, as well as a pro electric keyboard and acoustic guitar, if the spirit moves you (ask us about our moment in Woodstock music history). An open floor plan connects the living room to the kitchen, and beyond that a dining room with a 22 ft. cathedral ceiling and a sunken seating area. The master bedroom has a queen-sized bed, cable TV, private patio and semi-private bath, with rustic pine walls and ceiling. The second bedroom has a queen-sized bed, writer's desk, and north and west peek-a-boo windows which allow for sleeping under the stars while still providing total privacy. The third bedroom has a cozier feel with a double bed and extra built-in window seat (which one could sleep on, too) under another peek-a-boo window. The second (half) bath includes full laundry. The retains its 60's charm with a brand new stove and other updates. There is an open loft area above the dining room, accessible by ladder, and a bonus yoga room beyond. The decor is an eclectic mix of original and new pieces - lots of interesting things to look at. All of the mattresses are new and the towels and linens are high thread count cotton, washed with sensitive detergent. We have had nothing but good times in this vacation house for fifty years, and we know you will, too.br

3

Bed

1

Bath

5

Sleeps

$342.69

/ Nightly

Private Vacation Home

Woodstock Mountaintop Country Compound w. Pool & Sauna on 10 Acres

Woodstock, New York, United States

A newly-renovated home for your family just 4 minutes from Woodstock center! Surround yourself in nature in our Woodstock farmhouse and guest cottage, which sleeps 8+ and is surrounded by gardens, majestic mountain views, saline pool, wood-fired sauna. Perfect for longer stays with family or friends, work-from-home in the office and enjoy sunsets on the patio, lawn games on 10 acres of rolling fields, fully equipped modern kitchen and meals around our large dining room table.brbr---brbrOur newly-renovated home features gorgeous Catskill Mountain views. The first floor of the main house features a spacious and fully equipped chef's kitchen, large dining area, big living room with woodburning stove and home office. The second floor has two bedrooms with queen beds, and a baby's room with crib. Each floor has a full bathroom with gorgeous tiling and details. brbrOur guest cottage is fully equipped as a stand-alone, with living room, full bath, kitchenette and lofted bedroom. Perfect for families traveling with child-care-givers. brbrOutside you'll find 10 acres of meadow and forest with mountain views, a large deck equipped with comfortable furniture, and a wood-fired sauna. br brAll of our appliances are new, including induction stove, ovens, refrigerator, washing machine, dishwasher and more. Giant windows admit light at every hour of the day, and were just installed this year. brbrThe Wifi and television with Hulu, HBOGo, Roku, and Sonos are also provided, as well as electric car charger.brbrThe home is perfect for couples or a family looking to settle in for several weeks and enjoy the Catskills, with all the ease and convenience of working from home.

4

Bed

3

Bath

10

Sleeps

$171.73

/ Nightly

Private Vacation Home

Mid-Century Woodstock Retreat

Woodstock, New York, United States

Welcome to our mid-century Woodstock retreat! This one-level home features an open-concept layout that seamlessly blends the kitchen, dining, and living spaces, creating the perfect setting for family gatherings and entertaining friends. As you step inside, you'll be greeted by an abundance of natural light pouring in through large windows on two sides. The house is on the west side of Woodstock, set back from the street on a secluded driveway. It's a just a 3 min drive to the center of town!brbrSome info about the house:br- 3 bed/1 bathbr- 2 of the bedrooms have a queen bed and the other has 2 twin bedsbr- All bedrooms have blackout shadesbr- Hardwood floors throughoutbr- Renovated and fully equipped kitchen with dishwasher, electric oven, induction stove, microwave and Nespresso machinebr- Brand new washer and dryerbr- Wood-burning fireplace in living areabr- 65 inch TV with AppleTVbr- Small koi fish pond in the backyardbr- BBQ grillbrbrSome info about the location:br- 3 min drive to downtown Woodstockbr- 5 min walk to Sunfrost Farms grocery storebr- 33 min drive to Belleayre Ski Resortbr- 36 min drive to Hunter Mountainbr- 2 min drive to Bearsville Theaterbrbr*** For stays less than 90 days, please contact me ***

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Bath

Sleeps

$537.6

/ Nightly

Private Vacation Home

Exclusive Escape - Monthly Rentals

Woodstock, New York, United States

Escape to the mountains while enjoying all the luxurious comforts of home. From designer bedding to handmade leather sofa imported from Italy, no detail was spared in this high end retreat.brbrHave a furry family member No problem, we are also dog friendly!

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Bath

Sleeps

$476.5

/ Nightly

Private Vacation Home

Maple House: Private/Romantic Walk-to-Town Oasis

Woodstock, New York, United States

Treat yourself to a romantic getaway or relaxing retreat in your own newly-renovated historic farmhouse, ideally located on a quiet dead-end lane just one block from the Woodstock Village Green ~ the heart of this famous “colony of the arts”. You can walk to restaurants, cafes, galleries, boutiques, theaters, clubs, swimming holes and hiking trails. Or you can just stay home and relax in your private oasis of peace and beauty with a fully-fenced double-lot landscaped backyard, bluestone patio, gas-fueled fireplace, chef’s kitchen, extra-deep heated soaking tub, and other luxury amenities.brbrHOUSE HISTORY/LOCATIONbrMaple House was built in 1916 and is one of the original homes on Maple Lane, a quiet side street that borders Mower’s Field. One of the last surviving American maple trees that once lined the street stills stands in front of the house! On summer weekends, Maple Lane is transformed from a sleepy residential neighborhood into a hub of activity when the famous Woodstock Flea Market takes place in Mower’s Field every Saturday/Sunday from May-October. You can join in the fun and hunt for bargains/collectibles, or observe the festivities from the comfort of your covered front porch. Or you can retreat to the peace and quiet of the house interior or your spacious backyard surrounded by a tall privacy fence ~ and you’ll never know the market (or anything else) is there!brbrIn its 100-year history, Maple House has only had 4 owners, and all have been artists or musicians. (The internationally acclaimed singer-songwriter Tom Pacheco shot the cover for one of his albums in the backyard.) The current owners are artist-designers, and they have lovingly and expertly restored and upgraded the house to include modern conveniences and luxury amenities, while still retaining its original character and charm. The wood floors, woodwork, windows, staircase and fireplace have been restored to their original like-new condition, while the 2 bathrooms and the kitchen have been totally renovated and updated.brbrKITCHENbrThe kitchen has been transformed into a chef’s paradise! It features a vaulted ceiling with exposed beams and a ceiling fan, gleaming white quartz countertops, high-end charcoal-gray appliances and cookware, and a waterfall peninsula with bar seating for 3 in a plant-filled solarium that opens onto a bluestone patio (with outdoor seating and a brand new Weber gas grill).brbrYou can pick up groceries at the local natural foods market, farm stand, bakery, meat market and wine shop (all within walking distance), and prepare elaborate meals or simple snacks in your dream kitchen. Or you can leave the cooking to someone else and treat yourself to a meal at one of Woodstock’s renowned restaurants, many of which are just a block or two away, including: Silvia, Garden Cafe, Oriole 9, Tinker Taco, Cucina, Shindig, The Pub, Station Bar, Early Terrible, Catskill Mountain Pizza, etc.brbrLIVING/DINING AREAbrEntertain friends, play games, watch movies, listen to music or share meals in your spacious living/dining area, which is designed to be cozy, romantic and social. You’ll find a collection of albums for the record player, bluetooth speakers for the house playlist or your own music, card and board games, barware, and a teak table that comfortably seats 6 and has been well-proven for both family games and dinners alike. The living area features a rustic wood slab coffee table surrounded by new leather lounge seating with oversize throw pillows, where you can snuggle with a book, watch a movie on the wall-mounted flatscreen TV ~ or simply take a nap! In the wintertime, you can flip a switch to instantly light a fire in the gas-fueled fireplace and create a cozy romantic atmosphere (no wood-chopping or fire-building skills required!).brbr2 BATHROOMSbrMaple House has two spa-like bathrooms, one on each floor. Both are newly remodeled, modern and heated. The downstairs bathroom features a frameless glass shower with a rain head. The upstairs bathroom has an extra deep soaking tub (also with a shower head and a quartz seat). Once you draw your bath, the tub will automatically heat and gently recirculate the water to maintain the temperature you set, so you don’t have to refill. Instead you can just lay back, close your eyes, and float away ~ perhaps to the sound of music playing on the bathroom bluetooth speakers (for your own personal spa-cation experience)!brbr2 BEDROOMSbrThere are also two bedrooms on the second floor, both with midnight-blue painted wide-board floors, wood ceilings with exposed beams, queen-size platform beds with brand new Serta Beautyrest mattresses and luxury linens, black out shades, plenty of wardrobe space, full-length mirrors, and rustic furniture that captures the spirit of the Catskills.brbrHEAT/ACbrThe newly expanded thermostat-controlled hydronic heating system will keep you toasty warm during the winter months, and air conditioning units in both bedrooms and the living/dining area will keep you cool and comfortable in the summer.brbrBACKYARDbrYour fully-fenced double-lot backyard truly is a private oasis in the heart of the village. It features a sunny lawn surrounded by perennial gardens, flowering shrubs, and a variety of trees, including 2 Japanese maples (which turn fiery red in the fall) and a crabapple tree (which is adorned with delicate white blossoms in the spring). Two rustic handmade “chairs” have been carved from the trunk of a fallen 100-year-old pine tree that once stood on the property. In the summer, you can retreat to the shaded lounge area with a cushioned loveseat and two armchairs under the trees. Or you can stretch out in the sun on recliners and soak up the rays. The bluestone patio next to the kitchen has a brand new Weber gas grill, Tikki torches, and a table that seats 6 for cooking and dining al fresco.brbrNO CAR NEEDEDbrAlthough Maple House has private off-street parking for 2 cars, you don’t need a car to get here. You can simply ride the Adirondack Trailways bus from NYC or NJ and arrive at the Woodstock Village Green (just one block from the house) in only a few hours!brbrPETSbrSorry, but dogs are not permitted on the premises. Thank you for your understanding!brbrEASY TO CONTACTbrWe're happy to answer any questions you may have, either before booking or during your stay. We look forward to hearing from you, and welcoming you to Maple House for a peaceful and relaxing getaway!brbrShort-Term Rental Operating Permit #21N-114

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Bath

Sleeps

$319.37

/ Nightly

Private Vacation Home

Romantic Cottage -Amazing Views -Spa -Woodstock NY

Woodstock, New York, United States

Best Kept Secret Cottage with incredible views only 7 minutes from the center of Woodstock! brBath in the secluded romantic outdoor Spa Hot Tub!brThis home has ample space with an open bedroom, an upstairs den/sleeping area, and an additional sofa bed in the living room. It sleeps 2; however, we have a loft sofa bed for a young person or a child. Beautiful Modern amenities. Nicknamed The House With The View because of the breathtaking vista of the valleys and mountains of the Catskills! It is 20-30 min. from 2 Skiing Mountains Hunter/Bellaire. Experience its Magic! brWoodstock Mountain Cottage has incredible views and is 5.9 miles from the center of Woodstock. The house with the View was called because of its vantage point, which opened to an expanded breathtaking vista of the valleys and mountains of the Catskill. Newly added luxury outdoor Spa Hot Tub! No better place to relax than under the open skies. On a quiet road that some consider Woodstock's kept secret, the house is a gem waiting to be discovered. It was abandoned for over 20 years, then remodeled completely, maintaining some of its charming wooden beams dating 200 years old.brThis house is a combination of the old and the new. Locals love the location!brStrong Wifi brings civilization to you with a smart TV and free Netflix. ( no cable TV)brStainless steel appliances. One Queen-size bed and two sofa beds to accommodate 2-3 guests. Upper and lower decks with incredible views! Cappuccino machine, washer and dryer, Jacuzzi Bath Tub, and rainwater shower head.brPlease Note: The Space has an Open Floor Plan. The bedroom and Upper-level rooms are open Floors (not closed rooms). The stairs' Den/Sleeping area overlooks the main space, but the bottom Open Bedroom needs to be visible from the top room.brWoodstock - nestled in the pristine Catskills mountains, is one of the most famous small towns in the US, for a good reason -- artists, writers, and musicians have come here for the last 200 years to rest, get inspired, and create. The Love and Peace concert was birthed here, and remnants of the free love of the '60s can be felt everywhere. Woodstock is one of the most celebrated small towns in the world, following the 1969 concert. It was once the home of Bob Dylan and other famous musicians and artists. This small town with a big heart won many admirers with warm-hearted, welcoming residents. The number of yoga studios per capita is astounding. Healers, channellers, and peace-loving folks congregate in the peace circle on the Village Green for a drum circle every Sunday during the summer. Woodstock: where the esoteric, creative, and unique is the norm, and Free range describes not only chickens.brThe Willow home was called The House with the View for 200 years, inspiring generations of artists to set their canvases across from it and be inspired by the magnificent open landscape of the Catskill mountains, which stretched as far as the eye can see. Two trees on the property - an old grandmother Willow and a Catalpa tree - have inspired, healed, and supported whoever rests under their canopy. Consider sitting under the loving presence of these two magnificent trees or just strolling along one of the most pristine and beautiful roads in the Catskills and enjoying life!brPlease Note: A 4% tax is added to the price.brGuests may access all spaces.brWe have a lockbox, but I live nearby in case the guests need help.brWe have plenty of parking around the house, and you also have two bicycles with helmets and walk on Sickler, one of the most magical roads in the Catskills.brThe Woodstock general area does not have consistent cell phone service, including this location. However, we do have strong Wi-Fi and Wi-Fi calling from the house.brOr use this as a perfect place to unplug!brA 42 smart TV with Netflix and Hulu included so you can watch all the movies worldwide. One pet is allowed. enjoybrEnjoy Peace, Love, and LightbrShort term permit Number is 9687

1

Bed

1

Bath

2

Sleeps

$574.19

/ Nightly

Private Vacation Home

Charming 4-bedroom house on 2 acres in marvelous Woodstock with WiFi, AC

Woodstock, New York, United States

Nestled on 2 private acres surrounded by acres of woods, with a creek and views of a stream-fed pond. Conveniently located 10 minutes to Woodstock, and 12 minutes to historic Kingston. With 4 Bedrooms, 3 Bathrooms, Living Room, Sunroom, Dining Room, separate Lounge/Office, Second Living/Dining Room with Kitchenette there is plenty of room to spread out. The Office and Second Living Room have queen sofa beds, so the home comfortably sleeps 12. Outside you’ll find a covered porch, bluestone terrace, lawns, and a seasonal heated pool. Enjoy hiking and biking trails just a mile down the road, with countless trails beyond. Hunter and Belleayre Mountains are each less than 45 minutes away.

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$2544.0

/ Nightly

Private Vacation Home

Walk To Woodstock, Streamside W/In Ground Pool

Woodstock, New York, United States

Stunning country home with all the modern amenities & interior design you would want to have during your stay. Enjoy the sounds of the year round Sawkill from every room of the house. 5,000+ Sq.Ft. to roam, gourmet kitchen, 2 Master BR's, private balconies, 30 FT. ceilings, seperate studio space with projector screen and additional kitchen. BBQ on the bluestone patio that overlooks the in ground, heated, saline pool. Take an afternoon stroll into the village of Woodstock and then return to relax on the screened porch overlooking the stream. Perfect for a group of couples or family getaway. br

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$543.17

/ Nightly

Private Vacation Home

Woodstock/Entire house with pool 1.5 miles to Village Green. Very private.

Woodstock, New York, United States

Stylish and comfortable private home just 1.5 miles from Village Green with private lawn, woods. In ground pool with patio, furniture for lounging, reading, eating. Fenced in back yard. Living room has vaulted ceiling w skylights. Outside deck and grill. Great mountain views. Great for walking. Clean mountain air. Some dogs are permitted .brFully equipped kitchen for gourmet cooking. Quiet neighborhood with forest/wooded back yard. Lots of wildlife, great restaurants, and the magic of the Catskill Mountains. Deer and rabbits. Close to 30 restaurants, shopping, galleries, live music, and more. Perfect for one couple, or one couple with a child. ( Also 2 couples since there are 2 bedrooms and 1.5 baths.)

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$677.47

/ Nightly

Private Vacation Home

Gorgeous Villa w/ Mountain Views, pool, hot tub!

Woodstock, New York, United States

Please note this house has been rented under a previous owner for years with 5 star reviews, I also managed the house for the previous owner. Our beautiful Villa has amazing mountain views, a clean, modern design and is the perfect getaway to socialize & relax. It is ideally located for hiking & has a gorgeous, private salt water pool (mid May-Oct) and a wonderful hot tub which is open year round!

3

Bed

2

Bath

6

Sleeps

$466.67

/ Nightly

Private Vacation Home

Woodstock Artist's Retreat

Woodstock, New York, United States

Relax, create, and enjoy the Woodstock Artist's Retreat. 6 serene acres hugged by magical Overlook Mountain, Lewis Hollow . minutes to the town center, attractions, hiking trails, KTD - Karma Triyana Dharmachakra Temple , Overlook hotel ruins and fire tower, Indian Head , Plattecove reserve , Echo Lake, Sloan Gorge, Opus 40, Devil's Path Trail and Plattekill falls.

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$515.53

/ Nightly

Private Vacation Home

Gracious Woodstock Retreat -Walking Distance to Town

Woodstock, New York, United States

Elegant yet comfortable home in a rural wooded setting on 2 private acres, and only a 10 minute walk from town. King Bedroom Master Suite has panoramic views of the woods, marble bath and separate entrance. Huge Queen L-shaped Bedroom Suite with 2 Queen beds, one on each leg of the L; Sectional Sofa with 54 HDTV, Private Bath, and Separate entrance. Two additional bedrooms both have Queen Beds and share a bath. Fully equipped kitchen, WIFI, Fireplace/wood burning stove, Gas grill and 50 foot deck.brbrCheck-in Time starts at 5:00 PM and Check-out Time is 11:00 AM except by special arrangement.brbrOther Things to Note:brOur home is in a very peaceful neighborhood. In order to preserve that serenity for our neighbors, we rent our space for lodging only, rather than as a party venue. There are several wonderful places nearby that we recommend to our guests for their parties and events!

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$504.0

/ Nightly

Private Vacation Home

Brookside Retreat: streamside patio•outdoor fireplace•fenced yard•walk to town!

Woodstock, New York, United States

Brookside Retreat is ideally located on a quiet side street overlooking Tannery Brook, a year-round stream that flows through the center of Woodstock and right past the house!brbrThis historic artist’s bungalow features an extensive bluestone patio (with a built-in outdoor wood-burning fireplace and stone table with benches), a covered deck, and walkways that overlook the stream ~ as well as a spacious landscaped and fenced-in lawn.brbrThree bedrooms accommodate up to 6 people (see details below). In addition, there's a fully-equipped country kitchen; a dining area (seats 6); and a spacious living room with a cathedral ceiling, ceiling fan, skylights, 2-story north light windows, a gas-fueled fireplace with an exposed stone chimney ~ and a piano!brbrIn addition, there's a separate studio-office building with a desk, lounge area, and wall of sliding glass doors that overlook the patio.brbrBrookside Retreat is the perfect place for a romantic getaway, family vacation, or personal retreat!brbrBEDROOMSbrThere are 3 bedrooms, all with AC: br1) a first-floor master bedroom with a king-size bed, sliding glass doors that open onto a private deck, and an en suite bathroom with a shower; br2) a second-floor bedroom with a queen-size bed, cathedral ceiling, oversized windows, and a shared bathroom with a tub/shower;br3) a second-floor children's bedroom with a crib, changing table, toddler/twin bed, fold-out full-size futon couch, and blackout shades.brbrPETSbrWell-behaved and crate-trained dogs are considered ~ please ask. Please note that a $100/week pet fee per dog applies. We ask that dogs are not left alone and unsupervised in the house, unless they are in their crates. Thank you!brbrShort-Term Rental Operating Permit #19-0536

4

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2

Bath

6

Sleeps

$700.0

/ Nightly

Private Vacation Home

Private Woodstock Retreat – Heated Pool, Hot Tub & Fireplace on 5 Secluded Acres

Woodstock, New York, United States

Escape to your own private Catskills retreat—set on five peaceful wooded acres at the base of Overlook Mountain. This fully renovated 3-bedroom, 2-bath home blends modern comfort with relaxed country living, featuring a heated saltwater pool in summer, a year-round hot tub, a spacious deck and screened porch, and a warm wood-burning fireplace for cooler months.brbrWhether you're swimming under the sun, enjoying morning coffee in the screened porch, hiking nearby trails, or unwinding by the fire after a day in town, this home is designed for easy, comfortable getaways in every season.brbrOutdoor Living Designed for Relaxation:brbrSurrounded by mature trees and landscaped gardens, the property offers exceptional privacy while still being just minutes from town. You will enjoy:brbr- Private heated saltwater pool (open May–September)br- Year-round hot tub under the starsbr- Large deck with outdoor dining and lounge seatingbr- Beautiful screened-in porch for bug-free summer eveningsbr- Landscaped garden and open lawn areabr- Quiet wooded setting on 5 acresbr- Fire pit areabrbrThis is a true indoor-outdoor retreat—designed for relaxing, reconnecting, and enjoying nature.brbrbrIdeal for Every Season — This Home Is Designed to Be Enjoyed Year-Round:br- Summer: swim in the heated pool, dine outdoors, and relax in the garden. br- Fall: experience foliage season and cozy evenings by the fireplace.br- Winter: enjoy snowy walks, hot tub soaks, and fireside relaxation.br- Spring: watch the landscape come alive and enjoy peaceful outdoor time.brbrbrBright, Open Living Spaces:brbrInside, the home feels airy, welcoming, and thoughtfully updated. Large windows fill the living area with natural light and bring the outdoors in, while the open floor plan makes it easy for everyone to gather comfortably. Highlights include:brbr- Spacious open-concept living room, kitchen, and dining areabr- Cozy wood-burning fireplacebr- Fully renovated interiorbr- Comfortable seating and gathering spacesbr- Smart TV and fast Wi-Fibr- Central air conditioning and heatingbr- Clean, modern design throughoutbrbrThe space works equally well for quiet weekends, family vacations, or small group getaways.brbrbrFully Equipped Kitchen & Dining:brbrThe kitchen is designed for both everyday meals and relaxed entertaining. Features include:brbr- Modern appliancesbr- Fully stocked cookware and essentialsbr- Open layout connected to dining and living areasbr- Dining table for shared mealsbr- Easy access to the deck for outdoor diningbrbrWhether you're cooking a full dinner or enjoying takeout from town, everything you need is ready.brbrbrComfortable Bedrooms & Flexible Sleeping:brbrThe home comfortably accommodates families, couples, or small groups.brbrPrimary Bedroom:br- Comfortable king bedbr- Peaceful settingbr- Easy access to bathroombrbrBedroom Two:br- Double bedbr- Bright and comfortablebrbrBedroom Three:br- Twin bedsbrbrBathrooms:br- Two full bathroomsbr- Clean, modern finishesbr- Heated floorsbrbrbrPerfect Location — 5 Minutes to Center of Woodstock, Yet Completely Private:brbrYou'll enjoy the peace of a secluded wooded setting while being just minutes from everything that makes Woodstock special.brbrNearby:br- Restaurants, shops, and galleriesbr- Hiking and nature trails near Overlook Mountainbr- Skiing and winter activitiesbr- Farmers markets and local eventsbrbrYou get privacy, nature, and convenience—all in one stay.brbrbrLocation & Nearby Activities:brbrOur home is conveniently located near many of the region’s most popular destinations, including the equestrian events at HITS, and the ski mountains of Hunter, Belleayre, and Windham. The surrounding Catskills and Hudson Valley offer year-round activities—from hiking and skiing to dining, shopping, and exploring charming local towns.brbrWhether you're planning an active getaway or simply looking to relax and unwind, the house serves as an ideal and comfortable home base.brbrThe attached garage and side entrance are especially convenient during winter months, providing a warm, dry place for skis, boots, and outdoor gear.brbrbrGuest Support & Local Recommendations:brbrWe provide guests with a curated list of our favorite restaurants, bars, hikes, and local attractions—including family-friendly activities and hidden gems. We want you to enjoy the area like a local.brbrWe also have trusted local support available if needed, including professional cleaning and maintenance services, to ensure your stay is smooth and comfortable.brbrFor longer stays (over two weeks), a mid-stay cleaning is required to maintain the home’s cleanliness and comfort.brbrbrHouse Rules & Important Information: to ensure a peaceful and enjoyable stay for all guests:brbr- Maximum occupancy: 4 adults (plus children; flexibility may be considered depending on ages)br- Minimum renter age: 27br- No parties or eventsbr- Quiet residential settingbr- Two exterior security cameras are installed: Front door / doorbell & Driveway facing the garagebrbrThese cameras are used solely for safety and property monitoring.brbrA 4% Ulster County occupancy tax will be added to the reservation as required by local regulations.

3

Bed

2

Bath

6

Sleeps

$800.42

/ Nightly

Private Vacation Home

1876 Eyebrow Colonial Home on 36 acres, with pool and fully loaded game room

Woodstock, New York, United States

Beautifully Appointed 1876 country house with sweeping lawns and an expansive, enclosed bluestone patio that is perfect for BBQs or roasting s'mores in the fire pit. brbrThe house itself is spacious & loaded with charm. The kitchen is well-equipped with a butler's pantry formal dining room that seats 12 and overlooks the landscaped garden. A screened-in porch overlooks the lawns in front of the house. The large living room features a dramatic wood-burning fireplace, flat screen TV and comfortable seating. The master bedroom offers wonderful views of the woods and the occasional deer behind the house where acres of private hiking trails begin. brbrThe large barn, situated by a stream, has been converted into a game room complete with pool, ping-pong, foosball, air hockey, a basketball game, darts, etc. This insures that even if the weather is bad, there is always something fun to do!brbrEven if a storm knocks out power in Woodstock rest assured our generator would kick in and restore power to everything.brbrThe house is situated between Phoenicia & Woodstock and a short drive from local shops & farm stands.brbrbrHiking Trails: The carriage trails are extensive. We border state land which is approx 150 acres and misc. neighboring land of 600 acres. brbrAll holiday stays are subject to a 3 day minimum

3

Bed

3

Bath

8

Sleeps

Vacation Home Rentals By Owner In Woodstock, NY

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