Windsor County Hotels with Pools

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.

With a stay at Jackson Gore Village in Ludlow (Jackson Gore Base Area), you'll be within a 15-minute walk of Okemo Mountain Resort and Jackson Gore Parking. This family-friendly hotel is 18.8 mi (30.2 km) from Killington Resort and 0.3 mi (0.4 km) from The Ice House Ice Skating. Relax at the full-service spa, where you can enjoy massages and facials. You're sure to appreciate the convenience of ski-in/ski-out access at this hotel, which also features an outdoor pool and an indoor pool. Additional features at this hotel include complimentary wireless internet access, concierge services, and an arcade/game room. The complimentary ski shuttle makes getting to the slopes a breeze. 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. Event facilities at this hotel consist of a conference center and a meeting room. Free valet 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.

Welcome home! This charming 1500 square foot 3 bedroom condo at the historical Castle Hill Resort and Spa, has everything you need and more. Built in 2004 with many upgraded features, this home is in pristine condition. Prior to entering the unit, guests will have access to the ski/snowboard lockers for their equipment storage. Proceed into the mudroom where your outerwear can be stored. From here you will have access to the wide open living area which include a reclining chair, love seat and sleeper sofa. A great spot to enjoy a board game or watch a moving in front of the gas fireplace. They fully equipped kitchen and dining room are open to the living room area. You can enjoy a meal eaither at the large dining table or at the counter. The outdoor patio space has a barbecue for all guest to utilize during their stay all year round. The master suite has a king bed and a private bathroom with a jetted tub and HUGE shower. Two additional bedrooms have direct access to the second shared full bathroom. Bedroom 2 has a queen bed and bedroom three has a bunk bed (twin over full) and a twin trundle pull out bed. The Castle Hill Resort is uniquely nestled in the mountains and surrounds the historic Castle Inn, which is nestled on the National Register of historical places. Guests may access the optional luxury amenities including 2 tennis courts, a year-round outdoor heated pool/hot tub, the fitness center, and the Aveda Spa (for and additional cost). You may enjoy dining at the award winning Castle Inn Restaurant in the resort complex. Okemo Mountain Resort is 3.8 miles from Castle Hill.About pets:No 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: 23.About events:No events allowed.

Located in Woodstock (West Woodstock), On The River Inn is within a 5-minute drive of Union Arena Community Center and Five Elm Arches. This family-friendly hotel is 13 mi (20.9 km) from Killington Resort and 1.2 mi (1.9 km) from Ottaquechee River. Enjoy a range of recreational amenities, including an indoor pool, a hot tub, and a sauna. Additional amenities at this hotel include complimentary wireless internet access, an arcade/game room, and a picnic area. Enjoy a satisfying meal at 506 Bistro and Lounge serving guests of On The River Inn. Quench your thirst with your favorite drink at the bar/lounge. Featured amenities include complimentary wired internet access, a 24-hour front desk, and a library. Planning an event in Woodstock? This hotel has 10000 square feet (929 square meters) of space consisting of a conference center and a meeting room. Free self parking is available onsite. Make yourself at home in one of the 45 individually decorated guestrooms, featuring microwaves and LCD televisions. Your pillowtop bed comes with premium bedding. Complimentary wired and wireless internet access keeps you connected, and cable programming provides entertainment. Private bathrooms with shower/tub combinations feature 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.

Winterplace ground floor with stocked wood burning fireplace. 3 BR 2 bath condo! Perfect for a large family or 2 families. Ski locker behind wood shed for gear. Steps away from Mountain Road ski trail!!! Full kitchen with built in dry bar. Brand new washer/dryer, Indoor pool on premises. Memories waiting to be made!About pets:No 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: 25.About events:No events allowed.

Newly RenovatedProfessional Cleaners-Linens and towels laundered off siteRemote Check-InLocated mid-mountain at the base of Solitude Peak! After an amazing day of skiing or hiking relax in your roomy private retreat.-Master bedroom w/ a King bed and bathroom-Second bedroom w/ 3 single beds and 1 double and a bathroom-Roomy dining area-Powder room-Ski equipment room-Fully equipped kitchen-Fireplace-FREE wi-Fi and Parking-Access to rec center w/ pool, fitness room, hot tubs and more-Laundry in suiteAbout pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.High chair and Crib on site.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 6.About events:No events allowed.

Enjoy our trailside, ski in ski out condo. Located At the top of the A&B lifts. Skip the crowds at the Base! After an amazing day of skiing or hiking relax in your roomy private retreat.-Master bedroom w/ a Queen bed and bathroom-Second bedroom w/ 4 single beds and a bathroom-Sofa/bed in the living area-Roomy dining area-Ski equipment locker-Fully equipped kitchen-Fireplace-FREE wi-Fi and Parking-Access to rec center w/ pool and hot tubs -Laundry in suiteAbout pets:No 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: 25.About events:No events allowed.

Winterplace L-104 is a 3 bedroom, 2 Bath condo with Ski in-Ski out access. Walk out this first-floor unit and walk across the parking area to the top of the A/B lift. You can be on the Sunburst 6 lift before anyone else has even loaded the bottom lifts! That can mean a whole extra first tracks run for you and your family!This unit is close to the indoor pool and the 2 hot tubs are perfect after skiing all day. Winterplace is the first slopeside community to open in the fall and close in the spring!Newly remodeled kitchen, Washer/Dryer, large mudroom, wood burning fireplace (wood included)Sleeps 101st Bedroom- King bed2nd bedroom- Queen bed3rd bedroom- 2 Bunk Beds (sleeps 4)Queen Sofa Bed sleeps 2About pets:No 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: 25.About events:No events allowed.