Holiday rentals with a pool in Woodstock

Gorgeous Mountain View | Ski/Fast Wi-Fi/Wood Stove

Welcome to your amazing Catskills retreat in Hunter, NY! Marvel at the prime location with spectacular views situated only a 5 minute drive to Hunter Ski Mountain. Near hiking trails, waterfalls, antique shops and excellent restaurants. * 2 mins to Hunter North * 5 mins to Hunter base lodge * 13 mins to Windham * 15 mins to Colgate lake While at home enjoy views of the mountain on our deck - bask in the sun or grill a rack of ribs during the day or enjoy a glass of wine and stargaze at night.

Contemporary Guesthouse with Views and Privacy

Secluded studio on 13 acres in Bearsville with views of meadows, mountains and woods. Stand-alone guest house with queen size sleeping loft, kitchenette, fully tiled bathroom, elliptical trainer, and all amenities. Wake up in the morning and enjoy the amazing views with your coffee, hike in the woods, or meditate at the waterfall. In season enjoy the completely private heated pool. End the day with s'mores around the fire pit. An ideal getaway from the city yet only three miles to Woodstock.

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Welcome to The Evergreen, our Catskills retreat located 5 minutes from Woodstock village. Sitting on 3 acres amongst the trees, this property boasts beautiful outdoor space with a heated pool*, hot tub, outdoor dining area, grill, and a fire pit, creating the perfect setting for relaxation and entertainment. This charming property offers 5 bedrooms & 3 full bathrooms, perfect for large families or groups of friends. It also features a study, ideal for those who need to balance work and play.

Upstate Modern Scandinavian Barn in the Catskills

Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.

chezbevet-country cabin retreat

Town of Woodstock, NY permit No: 19H-017 Country Cabin Guest House Retreat in beautiful Woodstock, NY.Nestled in the mountains, near waterfalls and streams,3 miles from Village Green,5 min. from The KTD Monastery,10 min. from OPUS40 and HITS.Shopping,restaurants,skiing,hiking and the ambiance of Woodstock in the Catskill Mts.1 mile from Grammy Award Winner Levon Helm’s Rambles.Enjoy Maverick Concerts,Woodstock Playhouse and Historic Byrdcliff.The beautiful inground saltwater pool is now open

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Kapitan’s Cottage Private Winter Retreat Kingston

Escape the city to this cozy vintage rustic Catskills retreat—perfect for couples, families, and pet-friendly winter getaways. This 2BR, 1.5BA two-story home blends country charm with modern comforts, a large private yard, stone deck, fire pit, and BBQ. Close to skiing, hiking, parks, Kingston, Woodstock, and High Falls—yet secluded enough to truly unwind. Ideal for weekend or midweek escapes upstate. Pet-friendly, generator on-site. Inground salt pool open Mid May- Sept.

Tyrolean Style Country House in Saugerties, NY

Tyrolean style, two family house on two acres, (owner and family are onsite and lives in the bottom unit) fully furnished 3 bed, 2 bath home, fireplace. AC in master and living room only. WIFI throughout. Guests have separate parking, entrance, back deck with a big table & 8 chairs. The house is newly renovated, new luxurious bedding in each bedroom. Wake up surrounded by trees and to a beautiful sunrise. Perfect for a romantic weekend or family vacation.

Woodstock Family Home w/ Tree House + Heated Pool

Town of Woodstock Special Use (aka STR) Permit #23-0683. Featured in Hudson Valley Style Magazine, this fully updated modern farmhouse is ready to host. Radiant-heated full baths, whole-house generator, PRIVATE heated saltwater pool (schedule/weather permitting), four-season porch, indoor fireplace, fully equipped kitchen, outdoor grill, etc. Basement includes ping pong and pool tables. All bedrooms and full baths upstairs. Half bath on the main floor.

Gorgeous Villa MntnViews, nr SKI, firepl, hot tub!

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- mid Oct) and a wonderful hot tub which is open year round! In addition to the main house there is also a spacious studio cottage (with bathroom) & heat that can be used as a WFH private office. It has it's own high speed internet.

Warm & Comfortable Family Stay nr Woodstock

Hi, I’m Anna. I’m so glad you’re here, and I’d love to welcome you to Paradise Woodstock! Here are a few things I think you’ll especially enjoy about the house. Highlights: Sublime home with fireplace, screened porch, two living rooms, and chefs kitchen. Very private, yet minutes to Woodstock and Kingston. CLOSE TO SKI ACCESS • 20 miles to Hunter Mountain • 32 miles to Belleayre Mountain • 34 miles to Windham Resort