Best Windsor County Hotels

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.

When you stay at The Shire Woodstock in Woodstock, you'll be on a river, within a 15-minute drive of Quechee Gorge Bridge and Green Mountain National Forest. This hotel is 18.8 mi (30.3 km) from Dartmouth College and 15.5 mi (24.9 km) from Killington Resort. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and a picnic area. Featured amenities include a safe deposit box at the front desk and coffee/tea in a common area. Free self parking is available onsite. Stay in one of 53 guestrooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, complimentary toiletries, and hair dryers.

Located in Woodstock, Sleep Woodstock Motel is on a river, within a 10-minute drive of Union Arena Community Center and Long Trail Brewing Company. This motel is 7 mi (11.2 km) from Green Mountain National Forest and 10.3 mi (16.5 km) from Killington Resort. Make use of convenient amenities such as complimentary wireless internet access, tour/ticket assistance, and a picnic area. Featured amenities include express check-in and express check-out. Free self parking is available onsite. Make yourself at home in one of the 13 individually decorated guestrooms, featuring kitchenettes. 37-inch flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include desks and microwaves.

Located in Norwich, Norwich Inn is in the historical district, within a 5-minute drive of Dartmouth College and King Arthur Baking Company. This hotel is 1.4 mi (2.2 km) from Montshire Museum of Science and 2.2 mi (3.5 km) from Thompson Arena. Take advantage of recreation opportunities such as a 24-hour fitness center or take in the view from a terrace and a garden. Additional features at this hotel include complimentary wireless internet access, gift shops/newsstands, and a fireplace in the lobby. You can enjoy a meal at On-Site Brew Pub serving the guests of Norwich Inn, or stop in at the grocery/convenience store. Wrap up your day with a drink at the bar/lounge. Buffet breakfasts are available daily from 7:30 AM to 10:30 AM for a fee. Featured amenities include a 24-hour business center, a 24-hour front desk, and a library. Planning an event in Norwich? This hotel has 2000 square feet (180 square meters) of space consisting of conference space and meeting rooms. A roundtrip airport shuttle is provided for a surcharge (available 24 hours), and free self parking is available onsite. Make yourself at home in one of the 39 individually decorated guestrooms, featuring iPod docking stations and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with bathtubs or showers feature designer toiletries and hair dryers. Conveniences include desks and ceiling fans, as well as phones with free local calls.

With a stay at Castle Hill Resort And Spa 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 luxury hotel is 12.8 mi (20.5 km) from Green Mountain National Forest and 2.1 mi (3.4 km) from Phineas Gage Memorial. Pamper yourself with a visit to the spa, which offers massages, body treatments, and facials. You can take advantage of recreational amenities such as an outdoor pool, an indoor pool, and a hot tub. This hotel also features complimentary wireless internet access, concierge services, and an arcade/game room. Satisfy your appetite for dinner at the hotel's restaurant, Castle Dining, or stay in and take advantage of the room service (during limited hours). Quench your thirst with your favorite drink at the bar/lounge. Featured amenities include complimentary wired internet access, complimentary newspapers in the lobby, and a 24-hour front desk. Event facilities at this hotel consist of a conference center and 3 meeting rooms. Free self parking is available onsite. Stay in one of 10 guestrooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and satellite programming is available for your entertainment. Private bathrooms with bathtubs or showers feature designer toiletries and hair dryers. Conveniences include complimentary newspapers and coffee/tea makers, as well as phones with free local calls.