Resorts in Windsor County

With a stay at Pointe at Castle Hill Resort in Cavendish, you'll be near ski lifts, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School for the Arts and Crafts. This spa hotel is 2.1 mi (3.4 km) from Phineas Gage Memorial and 3.3 mi (5.2 km) from Dorsey Park. Relax at the full-service spa, where you can enjoy massages and facials. You can take advantage of recreational amenities such as an indoor pool, a hot tub, and a fitness center. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and an arcade/game room. At Pointe at Castle Hill Resort, enjoy a satisfying meal at the restaurant. Wrap up your day with a drink at the bar/lounge. Featured amenities include a business center, a 24-hour front desk, and luggage storage. Event facilities at this hotel consist of a conference center and meeting rooms. Free self parking is available onsite. Stay in one of 96 guestrooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with shower/tub combinations feature complimentary toiletries and hair dryers. Conveniences include desks and coffee/tea makers, as well as phones with free local calls.

A stay at Woodstock Inn & Resort places you in the heart of Woodstock, a 1-minute drive from Billings Farm and Museum and 7 minutes from Saskadena Six Ski Area. This golf resort is 4.9 mi (7.8 km) from Sugarbush Farm and 7.1 mi (11.5 km) from Simon Pearce Mill. Relax at the full-service spa, where you can enjoy massages, body treatments, and facials. After practicing your swing on the golf course, you can dip into one of the 2 hot tubs. This resort also features complimentary wireless internet access, concierge services, and an arcade/game room. Enjoy American cuisine at Red Rooster Restaurant, one of the resort's 4 restaurants, or stay in and take advantage of the room service (during limited hours). Need to unwind? Take a break with a tasty beverage at one of the 2 bars/lounges. Full breakfasts are available daily from 7 AM to 10:30 AM for a fee. Featured amenities include a business center, dry cleaning/laundry services, and a 24-hour front desk. Free valet parking is available onsite. Make yourself at home in one of the 142 individually decorated guestrooms, featuring refrigerators and flat-screen televisions. Your pillowtop bed comes with premium bedding. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature shower/tub combinations, complimentary toiletries, and hair dryers.

When you think of vacationing in Vermont, your mind might go to romantic getaways and extreme winter sports. While those are true, families will also find that Vermont is a great place to spend time together sledding, hiking, apple picking and even having a few snowball fights. Located in Brownsville, our Mount Ascutney Resort is a mountainside retreat, perfect for both couples’ getaways and outdoor family vacations. The resort features a farm-to-table restaurant, indoor and outdoor pools, an arcade and tennis courts. For beautiful views of the Green Mountain state, head to the tippy top of Mt. Ascutney State Park or hit the slopes at Mt. Sunapee or Killington. Or go rafting, kayaking and hiking to see the area’s gorgeous fall foliage. In between mountain adventures, discover the quaint towns of Quechee and Windsor, play a round of golf at a nearby course, or check out some of Vermont’s hot spots, like Harpoon Brewery, Quechee Gorge, Simon Pearce restaurant and glassblowers, Billings Farm and Museum, Sugarbush Farm and more. Our mountain resort in Mt. Ascutney features spacious one-, two- and three-bedroom villas, some with two stories, from 970 to 1,600 square feet. Families love the spacious living room, full-sized kitchen and convenient laundry facilities on property. Please note there is a resort fee that includes a variety of onsite amenities.

With a stay at Jackson Gore Village, A Vail Resorts Property in Ludlow (Jackson Gore Base Area), you'll be within a 5-minute drive of Okemo Mountain Resort and Jackson Gore Parking. This family-friendly hotel is 16.4 mi (26.4 km) from Killington Resort and 0.3 mi (0.6 km) from The Ice House Ice Skating. Enjoy the convenience of ski-in/ski-out access at this hotel, which also features 3 hot tubs. This hotel also features complimentary wireless internet access, an arcade/game room, and ski storage. You'll be on the slopes in no time with the complimentary ski shuttle. Satisfy your appetite at Coleman Brook Tavern, one of the hotel's 2 restaurants. Quench your thirst with your favorite drink at the bar/lounge. Cooked-to-order breakfasts are served on weekdays from 8:00 AM to 10:00 AM for a fee. Featured amenities include a business center, dry cleaning/laundry services, and a 24-hour front desk. Free self parking is available onsite. Make yourself at home in one of the 200 individually decorated guestrooms, featuring DVD players and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms with shower/tub combinations feature deep soaking bathtubs and complimentary toiletries. Conveniences include phones, as well as safes and washers/dryers.

With a stay at Winterplace at Okemo, A Vail Resorts Property in Ludlow (Clock Tower Base Area), you'll be steps from Okemo Mountain Resort and Snow Stars Carpet. This ski aparthotel is 0.1 mi (0.1 km) from Skywalker Carpet and 0.3 mi (0.4 km) from General Parking. Enjoy the convenience of ski-in/ski-out access at this aparthotel, which also features an indoor pool and a hot tub. This aparthotel also features complimentary wireless internet access and barbecue grills. Featured amenities include express check-out and laundry facilities. Free self parking is available onsite. Treat yourself to a stay in one of the 5 individually decorated guestrooms, featuring fireplaces and flat-screen televisions. Kitchens are outfitted with refrigerators and microwaves. Cable programming and DVD players are provided for your entertainment, while complimentary wireless internet access keeps you connected.

With a stay at Mountain Lodge at Okemo, A Vail Resorts Property in Ludlow (Clock Tower Base Area), you'll be steps from Okemo Mountain Resort and General Parking. This family-friendly hotel is 0.2 mi (0.3 km) from B Ski Lift and 0.2 mi (0.3 km) from A Ski Lift. After a day on the slopes, enjoy recreational amenities including a fitness center and bicycles to rent. This hotel also features complimentary wireless internet access, concierge services, and babysitting (surcharge). Guests can get around on the complimentary shuttle, which operates within 0.50 mi. At Mountain Lodge at Okemo, A Vail Resorts Property, enjoy a satisfying meal at the restaurant. Featured amenities include dry cleaning/laundry services, luggage storage, and laundry facilities. Guests may use a train station pick-up service for a surcharge, and free self parking is available onsite. Treat yourself to a stay in one of the 50 individually decorated guestrooms, featuring fireplaces. Rooms have private balconies or patios. Kitchens are outfitted with full-sized refrigerators/freezers, ovens, and stovetops. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment.

With a stay at Okemo Mountain Lodging by Vail Resorts in Ludlow (Clock Tower Base Area), you'll be steps from Okemo Mountain Resort and Snow Stars Carpet. This vacation home is 0.1 mi (0.1 km) from Skywalker Carpet and 0.3 mi (0.4 km) from General Parking. This smoke-free vacation home features snowboarding nearby, skiing lessons nearby, and sledding nearby. Recreational activities include snow tubing nearby, downhill skiing nearby, and cross-country skiing nearby. Free self parking is available onsite. Make yourself at home in one of the 25 individually decorated guestrooms, featuring kitchens with full-sized refrigerators/freezers and ovens. 47-inch LCD televisions are provided, with cable programming available. Conveniences include separate sitting areas and microwaves, and housekeeping is provided on request.