Boutique Hotels in Woodstock

You will be Catskillin' it in this newly remodeled, over 500 sq. ft., design-forward 1BR cottage, bright and snug with private outdoor space, modern kitchenette (only induction burner, microwave, and convection toaster oven,) and spa-like bathroom. Upstate and chill in the cozy full bed with your s.o. for a romantic cottage getaway. A comfy second bed makes it great for get-aways with your bestie, too. Located on a dead-end street, equipped with AC, heat, high speed internet, and private parking. No car, no problem: Trailways bus less than a mile away! Overlook Mountain rising over the treetops, short walk to village center, with its music venues and lively restaurant scene. Ideal location for any season: hit the trails, hit the slopes (35 minutes to Bellaeyre), hit the hay. Central to all that the Catskills have to offer.Town of Woodstock STR Permit #22H-266About pets:No pets allowed.About checkOut:Check out before 12:00 PM.About children:Children allowed: ages 0-17.About customRules:Only two people maximum. Out insurance does not cover more than two individuals at once, including children..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

With a stay at Coldbrook Bed and Breakfast in Bearsville, you'll be 8.8 mi (14.1 km) from Ashokan Rail Trail- Woodstock Dike Trailhead and 21.2 mi (34.1 km) from Hunter Mountain. This bed & breakfast is 26.4 mi (42.5 km) from Kaaterskill Falls. Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. A complimentary self-serve breakfast is served daily from 6:00 AM to noon. Featured amenities include microwave in a common area and refrigerator in a common area. Free self parking is available onsite. Make yourself at home in one of the 3 individually decorated guestrooms, featuring refrigerators and microwaves. Your memory foam bed comes with Egyptian cotton sheets. Rooms have private patios. Prepare your meals in the shared/communal kitchen. 55-inch flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms feature showers, complimentary toiletries, and hair dryers.

This is a newly renovated apartment in and old studio. Close (1 mile) to the center of the village of Woodstock, NY. Within a few miles of some of the most wonderful walks you'll find anywhere. Minutes away from all kinds of delightful restaurants. Less than an hour away from the trailheads of many of the great Catskill trails. Oh yeah - and great music at a number of venues in and around Woodstock! The lake in the photos is 1 1/2 miles from the studio.About pets:Pets allowed: dogs and cats (limit 2 total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

This one-of-a-kind converted barn is conveniently located between Woodstock and Phoenicia, 2 hours north of NYC. With four bedrooms and three full bathrooms the house sleeps up to 6 people and is ideally suited for families, with a maximum of two couples (plus kids). Old & new seamlessly converge in the design of this home. The spacious, open floor plan on the first floor features a Great Room with soaring, 29 foot ceilings & twig chandeliers. Gaze up at the exposed, hand-hewn, 19th century beams... watch a movie on the large flat screen TV... get cozy in front of the gigantic, antique blue stone fireplace. Tastefully decorated with fine antique & modern furnishings and original artwork throughout this home is memorable and unique. The fully equipped, chef's kitchen includes a Viking professional range, double Dacor ovens, a dishwasher, stainless steel refrigerator/freezer, and a palatial kitchen island with soapstone top. An oversized, mahogany dining table seats 6. For cooking enthusiasts-- you will find all kinds of cookware, serving dishes, cocktail glasses and wine stemware... Outdoors there is a large, Weber gas grill (propane provided) and a Weber charcoal grill (bring your own briquettes). There is ample outdoor dining spaces-- a picnic table in the screened porch, a teak table on the streamside deck, and a large, round concrete table with sun umbrella poolside, overlooking the gardens.We are well prepared for executives working from home, and/or kids doing remote learning. We have Spectrum's Ultra fast internet package and three Orbis to strengthen the signal throughout the home. The den on the first floor (located behind the dining area) has a full sized desk with an ergonomic, adjustable chair and a newly purchased Canon laser printer and a smart TV. We have a landline which can be used from this area as well. Privacy blinds have been installed on these windows. The huge farmhouse table in the living room can double as a workstation and the twin bedroom on the first floor has a small desk. The fully private grounds are beautifully landscaped with mature trees, ornamental shrubs, and perennial flowers. There are ample outdoor entertaining spaces. Dine al fresco on the deck or in the spacious screened-in porch. Relax on a poolside lounger surrounded by manicured gardens. Take a dip in the heated pool.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.Renter must sign supplemental rental agreement..About customRules:Renter must sign supplemental rental agreement and.For security reasons we require verification of yo.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 30.About events:No events allowed.

Renovated 3,000 SF home about 25min drive to Bellayre Mountain and 8 min drive to Woodstock town, our 35 acres provides total privacy and unparalleled views and serenity. This 3-bedroom guesthouse is found at the end of a long private driveway off a dead-end road shared with the main house that is sometimes occupied by owner about 100 yards away. Enjoy the warm fireplace, a generous kitchen, porch, outdoor BBQ and wooded trails. Take in the beauty of ponds, starry nights and miles of nature trails that wind through the forest, across meadows, by streams and along stone walls, affording you stunning views and the sounds of nature.About pets:Pets allowed: dogs and cats less than 20 lbs per pet (limit one pet total).Describe ur dog before booking; Extra fees p/pet.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.Families are welcome.About customRules:Please provide the names and ages of all parties in the group and a detailed description of the pet, if applicable, within 24 hours of booking..A maximum of two cars are allowed to park at the property. Any additional vehicles or visiting guests must be approved within 24 hours of booking.,Traveler must answer all questions within 48 hr of booking. Number of visitors must not exceed the property's capacity at any time without approval..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.Need to discuss if party or event is desired.

Florentine is a peaceful sanctuary on 15 acres of lawn, fruit trees, and forest near Woodstock. Designed by architect Barry Price, it invites rest, beauty, and reconnection. Mountain views, golden sunsets, a chef’s kitchen, fast Wi-Fi, and sacred stillness await. Autumn brings vibrant foliage, cozy fires, and Thanksgiving gatherings; winter offers fresh snow, starry skies, and warmth by the hearth—ideal for couples, creatives, families & healers.Florentine - Golden Light Retreat near Woodstock invites you into a sanctuary bathed in golden light, where soulful design and nature converge to uplift your spirit and nourish creative renewal. Perched across 15 acres of gently rolling lawns, fruit trees, and forested hills, this luminous 3,500 sq. ft. home pulses with a warm, grounded energy that welcomes calm, beauty, and deep rest.Sunlight pours through 10 loft-style windows, flooding the open-plan living areas with a soft glow that shifts with the day—from pale dawn to fiery sunset. Built with high-level craftsmanship, reclaimed wood, and natural materials, the house itself is a vessel of harmony and comfort. A centered fireplace offers cozy evenings, while expansive mountain views stand as timeless guardians outside your windows.A Seasonal InvitationIn autumn, Florentine radiates even more magic—golden leaves, crisp mountain air, and starry Catskill nights. Guests cozy by the fireplace after hikes, savor sunsets from the porch, and gather around the fire bowl as the season shifts.Special for Thanksgiving: Florentine’s spacious chef’s kitchen, generous dining area, and glowing fireplace make it the perfect setting for family connection, shared meals, and gratitude-filled gatherings. Whether preparing a feast or simply soaking in the mountain beauty, Thanksgiving here feels timeless and unforgettable.Winter brings fresh snow, stillness, and beauty in every direction; summer invites deep refreshment with hammock naps and the invigorating open-sky shower (open end of May through September).Awaken to birdsong and the scent of the forest. Rest on the screened hammock porch, refresh in the outdoor shower, and gather around the fire bowl beneath a blanket of stars. Inside, a chef’s kitchen with a generous island invites shared meals and long conversations. - Restful, Thoughtfully Designed BedroomsFlorentine offers four lovingly appointed bedrooms, each with its own energy and purpose. The master suite (king) features mountain views, a writing nook, and a private soaking-tub bathroom wrapped in windows. The queen bedroom carries antique charm and quiet elegance, perfect for a second couple or guest seeking privacy. The full bedroom is cozy and creative, with a work desk and woodland views. The twin bedroom offers two twin beds—light-filled and playful—ideal for children, friends, or the young at heart.The three guest bedrooms upstairs share a beautiful full bathroom, while an additional full bath on the lower level provides extra comfort and flexibility for families and groups. Each room includes its own mini-split for personalized climate control, natural linens, and calming textures that support deep rest and renewal.- Comfort & ConnectivityFlorentine now features mini-split climate control in every bedroom and across the main floor (living, dining, kitchen) for personalized comfort in all seasons. The basement movie/fitness room is with radiant heat equipped. The entire house (including the mini-splits and all electric systems) is powered by solar energy, supporting sustainable stays. We also use eco-friendly cleaning products to honor both you and the land. Internet is strong (520 Mbps), with a new router just installed—making the house perfect for remote work, online meetings, or creative retreats while staying connected in nature.- Unique AmenitiesInvigorating outdoor open-sky shower (seasonal)Screened hammock porch for meditative restChef’s kitchen with spacious islandForest + lawn trails for wandering and quiet reflectionFire bowl for evening connection under the starsMini-splits in every bedroom + main floorWhole-house solar power (sustainable energy)High-speed Wi-Fi (520 Mbps, new router)Eco-friendly cleaning practices- Location & AccessFlorentine is located just minutes from the shops, cafes, and hiking trails of Woodstock and Phoenicia, as well as accessible for day trips to ski trails in Belleayre, Hunter & Windham. You’re close to everything—but feel worlds away. Winter travelers will find the house accessible (with 4WD recommended in snow). Summer guests often report feeling deeply refreshed by the lush surroundings, the tranquility—and the invigorating outdoor shower beneath the open sky.- Please NoteThe house is meticulously cleaned and energetically prepared between guests. Our beloved cat is confined to the main floor when we are present; light traces may remain—guests with severe allergies should take this into account. No dogs are allowed. Florentine is not suited for parties or large gatherings; she is meant for intimate retreats, creative recharge, and meaningful connection.- Rates & Booking Details(Minimum stay: 2 nights weekends, 3 nights weekdays/holidays)Weekday nights: $350–$450Weekend nights: $500–$650Holiday nights: $550–$750- Discounts11% off for 7-day stays22% off for 1-month stays- Reservation Notes & Hosting DetailsUpon confirmation, guests will receive:A detailed House Inventory & Supply ListLocal Woodstock Activity SheetDriving DirectionsKey Instructions for check-in- For winter guests: our neighbor plows the road once snowfall slows, but a 4-wheel drive is recommended—the view is worth it .- Hosting LicenseThoughtfully priced for design, comfort, and location; Permit ID #21N-224 ensures fully licensed, professional hosting.- Final NoteFlorentine is an energetically attuned space ideal for peaceful retreats, remote work, and sacred rest. Many of our guests are healers, artists, families, and couples who return again and again—drawn by something they can’t quite name, but deeply remember. If you’re seeking a place that meets you on a soul level while offering modern comfort, sustainable systems, and beauty, Florentine is ready to welcome you home.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:PET POLICY: Absolutely no pets allowed Security Deposit - if you damage the home, you may be charged up to $1000.***Please note this house is not for you 1.) if you are hyper allergic to cats (cats have been previously on the main floor/living room),2.) if you you want to party with a group of 6 or more (this is a family home, so best suited for couples or families who want to enjoy the nature).About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.

Charming Willow Silo nestled amongst the trees 10 minutes away from Woodstock and 15 minutes away from Phoenicia, this wonderous three story tower is as well positioned to hiking nearby woods and mountains, as well as waterfalls. Wake up to a spectacular view of the mountain from the main bedroom or deck and end the evening stargazing from our own hammock by night. Secluded in the woods for a perfect relaxation retreat but close enough to everything.PERMIT No: 23N-277The spaceThis three story silo is unique yet cozy with amazing views. There are three bedrooms which are outfitted with two twin beds, queen bed and one full size sofa bed. Main bedroom has a full bathroom with a claw bath tub. Ground floor also has a full bathroom. The house is fully equipped with a brand new contemporary kitchen.Guests have access to a gas BBQ on the second floor deck, wifi and cable.***Please note the 2nd and 3rd bedrooms are adjoining rooms connected by a door***Guest accessEntry is by lockbox.Other things to notePlease Note: A 4WD vehicle is required during winter months in order to reach the hill where the Willow Silo is located.About pets:Pets allowed: dogs less than 50 lbs per pet (limit 2 pets total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 18.About events:No events allowed.

We are pleased to announce this beautiful, rustic, four-bedroom, luxury mountain getaway home is NOW being offered at unprecedently DISCOUNTED rates—particularly mid-week!Our very upscale, cedar log home is nestled in the prestigious, scenic Woodstock hamlet of Bearsville—home of the renowned Bearsville Theater, along one of Woodstock's most coveted, picturesque roads, and conveniently located within a minute’s drive of the famed Onteora Mountain House, the former majestic summer estate of Richard Hellman (Hellman’s mayonnaise), now a widely acclaimed bed and breakfast that is arguably the Hudson Valley's most sought after destination wedding venue. The home offers a true respite from today's hustle and bustle; set amidst nineteen totally private, wooded acres, surrounded by nothing but glorious, tranquil, and unspoiled nature, yet only minutes to the center of town! The home features soaring, two-story vaulted ceilings, heavy exposed log beams throughout, custom-milled wide-plank heart pine and natural slate tile floors. It is elegantly, yet comfortably furnished in the traditional rustic lodge-style of the Adirondack "Great Camps." It has a lovely, cozy, screened-in porch and expansive decking front and rear. The home is perfect for vacations, holidays, family gatherings, lodging when attending one of Woodstock's multitudes of music, art, crafts, theater, etc., events, or just a much-needed getaway!There are world class spas, including the award-winning Emerson Resort and Spa, heralded as “The Crown Jewel of Catskill Mountain Resorts,” and home of “The World's Largest Kaleidoscope,” just ten minutes away! A five-minute drive will take you to Kenneth Wilson State Park—featuring campgrounds, picnic-grounds with barbeque grills, hiking and mountain bike trails, swimming, and fishing lake. Experience true world-class dining at one of the area's many fine restaurants, including, Good Night, Cucina, Silvia, Early Terrible, just to name a few. Bread Alone, Oriole 9, and The Mud Club, are all top picks for breakfast and lunch! Outdoor activities abound! The area's beautiful lakes, mountains, rivers, along with outstanding art, cultural, and music scenes, provide plenty to do, whatever time of the year you visit. SPRING and SUMMER, you may enjoy water tubing and fly fishing on the Esopus Creek, canoeing and kayaking on the Hudson River, hiking, rock climbing, biking, tennis, golf, horseback riding and so much more. A five-minute drive from Woodstock’s town square is the trailhead to the renowned Overlook Mountain Wild Forest Preserve, with its marked trails and glorious views of the central Catskills, Ashokan Reservoir, and Hudson River Valley. At the summit is Woodstock’s historic, sixty-foot-high fire tower, one of only five remaining fire towers in the Catskill Park. Across from the trailhead is Karma Triyana Dharmachakra—the largest traditional Tibetan Buddhist Monastery in the USA. For shorter hikes, a five-minute stroll from the center of town is Comeau Park, with seventy-six acres of meadows, woods, and stream-front, offering a beautiful, tranquil walk, along Sawkill Stream.FALL is absolutely gorgeous; a great time to enjoy apple picking, pumpkin picking, pumpkin carving, and of course marveling at the incomparable foliage of the Catskills Mountains! October also marks the arrival of the renowned annual Woodstock Film Festival. The festival has drawn rave reviews nationwide from filmmakers, industry members, media, and film lovers alike. It has established itself as one of the top independent film events in the country, premiering exceptional films by established and emerging filmmakers. IndieWire has named it one of the top fifty film festivals in the world and Moviemaker included WFF as one of the “25 Coolest Film Festivals in the World.” The festival also features A-list concerts, parties, panels, and a host of additional innovative, and stimulating itinerary.WINTER offers plenty; nearby Hunter Mountain, Bellayre, and Windham Mountain are a skier’s paradise! There's also snow tubing, and even great sledding on the aptly named Sled Hill, just outside of town. The town of Woodstock especially comes to life in winter, with its signature displays of festive holiday lighting; very inviting and picturesque.ACCOMMODATIONS: Cedar Log Home, 4 Bedrooms + Loft with queen sleeper sofa, Daybed with trundle (2 twin mattresses), Great Room has an additional Daybed w/trundle, 3 Full Bathrooms (Sleeps up to 14)MAIN LIVING AREA: Soaring, two-story ceiling 32'x26' “Great Room,” the focal point of which is its massive Rumford-design wood-burning fireplace constructed with stone gathered from the property. GOURMET KITCHEN: Highlighted by a state-of-the art residential restaurant-style range featuring six, 23,000 BTU, open-style gas burners, a 30,000 BTU thermo-griddle, two ovens (one with optional convection), and an 18,000 BTU infrared broiler. Honed black granite countertops are featured throughout. Expansive center-island features built-in Viking microwave oven, trash compactor, and stainless-steel prep sink. Main sink is oversized in true restaurant-style and includes a waste disposal. BEDROOMS: Two separate “Owner’s Suite” wings, each with walk-in closet and ensuite bathroom. These bedrooms feature impressive, two-story, vaulted ceilings with exposed upper-story windowed dormers, lodge-style ceiling fans, and sliding doors leading to semi-private, covered porches, and deck. Both Owner’s Suites feature sumptuous king-sized, all-natural, organic latex mattresses. Ensuite bathrooms feature custom-built slate tile showers, with ceiling-mounted rain-shower-style showerheads, in addition to a handheld. The east wing's shower is a stunning six-foot by six-foot walk-in, featuring Hansgrohe's extraordinary twenty-four-inch Raindance showerhead, providing an exhilarating natural rain shower-like shower experience!THIRD BEDROOM: A bunk room-style set-up, featuring two beautiful log-built twin over queen-sized bunk beds (sleeps 6). It has a large picture window, ceiling fan, and a wall-mounted flat screen TV. MAIN BATHROOM: Features a corner-style shower with steam and handheld showerhead.DINING AREA: Features a large, custom crafted, Adirondack-rustic, bark-on hickory, and curly maple dining table that expands to eleven feet, and seats twelve comfortably. The dining area chandelier is crafted of genuine whitetail deer antlers. *Please note that antler products used throughout the home are all naturally shed; no animals harmed!UPSTAIRS LOFT: An expansive open space, featuring a vaulted log-beamed ceiling, lodge-style ceiling fan, exterior balcony/deck, comfortable faux-leather sleeper sofa with queen-sized mattress, custom-built, Adirondack-rustic, bark-on hickory and oak daybed with trundle (sleeps 2), 60' flat screen TV, and a premium stereo sound system w/full range, floor standing speakers, high-speed, wireless Internet (Wi-Fi) and cable TV.Location: Woodstock “Colony of the Arts” / “America's Most Famous Small Town.” Birthplace of the greatest music festival of all time that bears its name! Catskills, New York, USA (2 hours from NYC)About pets:Pets allowed.Well-trained, small sized non shedding dogs only.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:We request that large furniture pieces such as sofas, dining table, beds, etc., not be moved/rearranged..We request guests please not venture down into the basement (it is unfinished) unless there is a clear necessity, e.g., circuit breaker reset, etc.,All guests in your group should be made aware that recyclables, i.e. glass, plastics, aluminum cans, etc., must be kept separate from other garbage..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.Parties up to maximum 14 guest.

This lovely spot is just over a mile from the Woodstock Town Green, situated on a small road, nestled into a hillside, where you can watch the leaves change during the day and enjoy a cozy wood fire at night. A real feeling of privacy. Lots of room inside and out for relaxation. The grounds are an interesting combination of lawns, rock gardens, expanses of wood decking and stone work, sheltered nooks, and patio spaces—all designed informally around a fantastic in-ground heated salt water swimming pool. (Pool season is approximately from the end of May through September 15..)We are only minutes from the main venue for the Woodstock Comedy Festival and the Woodstock Film Festival. And this is a perfect spot to relax and watch the leaves change.The yard is fully fenced in, making it a great place for children and/or dogs (For insurance reasons we cannot accept Pit Bulls, Rottweilers, or Dobermans). The fenced portion includes the pool area, so supervision may be needed during the open-pool season. The house is a two-level bungalow dating from the late 1940’s, with Arts & Crafts-style inspiration. The inside is airy and light filled thanks to several sets of French doors and sliding panels that lead to outside. The eat-in kitchen is vintage, with updates for modern cooking. It is serviceable to the Thanksgiving dinner level , and it is lovely for cozy coffee klatching. The spacious, open living/dining area has a cathedral ceiling and wood-burning stone fireplace. There are three bedrooms and two bathrooms. Two of the bedrooms have queen-sized beds, and the third has an antique brass double bed. The third bedroom/study, upstairs, has a cathedral ceiling as well as a spectacular view. The house sleeps 6 adults comfortably. (If there are children, it may be possible to accommodate them on the pull-out futon couch—please discuss this with the property manager.) The house is stocked with the essentials you need to enjoy your stay. For the inside: soft sheets and towels, many pillows, firewood, plenty of cookware, plates and utensils, TV, broadband, a game console, books and DVDs, washer/dryer. For the outside: grill, pool toys, picnic and lounging furniture, hammock, and even a few sleds!For those who like to ski, Belleayre Mountain is only 30 minutes away.**For your own peace of mind, please purchase Trip Insurance.**About pets:Pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 28.About events:No events allowed.

When you a stay at The Herwood Inn in Woodstock, you'll be in the mountains, just steps from Catskill State Park and The Comeau Property. This luxury guesthouse is 11.4 mi (18.4 km) from Catskill Mountains and 28.5 mi (45.8 km) from Hunter Mountain. Take advantage of recreation opportunities such as a hot tub or take in the view from a terrace and a garden. Additional amenities at this guesthouse include complimentary wireless internet access and gift shops/newsstands. Free self parking is available onsite. Make yourself at home in one of the 4 individually decorated guestrooms, featuring kitchenettes. Your memory foam bed comes with Egyptian cotton sheets. 32-inch Smart televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Bathrooms with shower/tub combinations feature deep soaking bathtubs and rainfall showerheads.