Find 4-Star Hotels in Windsor County

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.

Located in Perkinsville, The Inn at Weathersfield is in the mountains, within a 15-minute drive of Springfield Hospital and Muckross State Park. This inn is 7.1 mi (11.5 km) from Mt Ascutney State Park and 15.1 mi (24.3 km) from Maple Lanes. Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. Additional amenities at this inn include concierge services, gift shops/newsstands, and wedding services. At The Inn at Weathersfield, enjoy a satisfying meal at the restaurant. Wrap up your day with a drink at the bar/lounge. A complimentary full breakfast is served daily from 7:30 AM to 9:30 AM. Featured amenities include express check-out, luggage storage, and laundry facilities. Free self parking is available onsite. Make yourself at home in one of the 12 individually decorated guestrooms, featuring DVD players and flat-screen televisions. Your memory foam bed comes with Egyptian cotton sheets. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers.

Located in Woodstock (West Woodstock), The Jackson is within a 5-minute drive of Union Arena Community Center and Five Elm Arches. This bed & breakfast is 13.4 mi (21.5 km) from Killington Resort and 1.1 mi (1.8 km) from Ottaquechee River. Take in the views from a terrace and a garden and make use of amenities such as complimentary wireless internet access. This Victorian bed & breakfast also features concierge services, a fireplace in the lobby, and a picnic area. Enjoy a satisfying meal at Oakes & Evelyn serving guests of The Jackson . Quench your thirst with your favorite drink at the bar/lounge. Cooked-to-order breakfasts are available daily from 7:00 AM to 10:00 AM for a fee. Featured amenities include express check-out, a library, and coffee/tea in a common area. Free self parking is available onsite. Stay in one of 11 guestrooms featuring Smart televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms have designer toiletries and hair dryers. Conveniences include blackout drapes/curtains, housekeeping is provided on request, and irons/ironing boards can be requested.

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 12.9 mi (20.8 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 a 24-hour front desk, a library, and an elevator. 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 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 stay at Deer Brook Inn in Woodstock, you'll be within a 10-minute drive of Long Trail Brewing Company and Union Arena Community Center. This bed & breakfast is 10.1 mi (16.2 km) from Killington Resort and 17.3 mi (27.8 km) from Pico Mountain at Killington Ski Resort. Free self parking is available onsite. Make yourself at home in one of the 5 guestrooms. Complimentary wireless internet access is available to keep you connected. Bathrooms feature bathtubs or showers, complimentary toiletries, and hair dryers.

With a stay at Solitude Village at Okemo by Vail Resorts in Ludlow (Clock Tower Base Area), you'll be within a 10-minute walk of Okemo Mountain Resort and General Parking. This ski aparthotel is 0.1 mi (0.1 km) from B Ski Lift and 0.1 mi (0.1 km) from A Ski Lift. Enjoy the convenience of ski-in/ski-out access at this aparthotel, which also features 2 hot tubs. Free self parking is available onsite. Treat yourself to a stay in one of the 15 individually decorated guestrooms, featuring fireplaces and flat-screen televisions. Kitchens are outfitted with refrigerators, stovetops, and microwaves. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment.

Exquisite four bedroom, four bath single family home located within one mile to the Quechee Club and amenities. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *This is a no pet/animal home. *Includes Quechee Club Access Z1040, Home Features: • 4 Bedroom, 4 Bath - Available for up to 8 Guests! • Open Concept Floorplan • Upstairs Loft • Wood Burning Stove • Free WiFi & Smart TVs • Pack 'n play and/or high chair may be available upon request (subject to availability) Excellent home for entertaining family and friends with the open concept floor plan. The main floor has 3 bedrooms and three full bathrooms. Open concept floor plan on the main level with the kitchen opens up to a large living/dining room area. The Master Bedroom suite has it's own private bathroom. Two more bedrooms complete the main level of the home. Upstairs is a fourth bedroom with it's own private bathroom. Bed Setup: King in master, Queen in second, two twins in third, and a Queen in upstairs loft.  Please pay close attention to following the house rules. Non compliance could result in sizable fines. - All guests staying at an Quechee Lakes Rentals by Portoro (Portoro Homes) are required to sign (esignature) a rental agreement and complete identity registration. - Age restrictions apply. Reservation holder must be 25 years of age. - Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Quechee Lakes Rentals by Portoro directly. - Known damages incurred during your stay must be reported to the property manager immediately. - Before check in, we will send you detailed directions to ensure a seamless arrival. - Check-in time is 3:00 p.m. Check-out time is 10:00 a.m. - We cannot guarantee early check ins or late checkouts. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night. - Some homes have cameras for external monitoring only. - In the State of Vermont and in Windsor County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. - There is no guard around the pools. - Use at your own risk. - This is a No Pets property. A daily rate fee of $150.00 will apply for violations and you may be asked to vacate the premises with no refund at the discretion of the Host. - This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host.

Experience the authentic charm and tranquility of Vermont at this stunning home in the Quechee Lakes community. We are committed to providing you with an extraordinary vacation experience, and this property is no exception. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *This is a no pet/animal home. *Includes Quechee Club Access Newton Village 9A, Home Features: • 3 Bedroom, 3.5 Bath - Available for up to 6 Guests! • Ample Seating & Cozy Fireplace • Breathtaking Views of Greenery • Fully Equipped Kitchen & Modern Appliances • Free WiFi & Smart TVs • Pack 'n play and/or high chair may be available upon request (subject to availability) Located in the Newton Village condos community: Newton Village condos in Quechee VT are the place to be. In addition to The Quechee Club, which is just a short walk away, Newton Village offers an on-site community swimming pool and tennis court! Newton Village is a private village located within walking distance to both Lake Pinneo and the Quechee Club. Newton Village is one of the newer villages, with construction having been completed in 2004. Enjoy access to The Quechee Club! [See: Guest Access] As you step into the living room, you'll be greeted by ample seating, a cozy fireplace, and large windows that offer breathtaking views of the lush greenery outside. It's the perfect spot for unwinding or entertaining guests. The fully equipped kitchen boasts modern appliances, granite countertops, and plenty of cabinet space, allowing you to cook up a storm on the gas stove while enjoying the bright and airy atmosphere. Adjacent to the kitchen, the dining area comfortably seats six and opens out to a lovely deck, ideal for al fresco dining. The main bedroom, located on the second floor, features a king-size bed, a private balcony and an en-suite bathroom, featuring a luxurious setup with a double sink vanity and a spacious shower. Large windows flood the room with natural light and offer serene views of the surrounding nature.  The second bedroom, on the second floor, features a queen-size bed and easy access to the main bathroom.  The third bedroom, situated in the basement, offers a quiet retreat with a queen-size bed, ample space and full bathroom.  Finally, an additional half bathroom is located on the first floor off the vestibule; all are equipped with modern fixtures and plenty of space. For your convenience, the property includes a laundry room equipped with a washer and dryer, located in the basement. The expansive outdoor areas, including a deck perfect for barbecues and a well-maintained lawn, allow you to enjoy the fresh Vermont air. As part of the Quechee Lakes community, the property also includes access to tennis courts and a swimming pool, enhancing your stay with extra activities. Surrounded by lush greenery, the property offers access to hiking trails, perfect for nature enthusiasts. Enjoy the scenic views of the nearby lake, adding to the tranquility and beauty of the location. Situated in a friendly and welcoming neighborhood, you'll have easy access to local amenities and attractions. At Quechee Lakes Rentals by Portoro, we take pride in curating exceptional vacation experiences. Whether you're looking for a peaceful getaway or a place to gather with friends and family, this Quechee Lakes rental provides the ideal setting. Book your stay today and immerse yourself in the beauty and comfort of Vermont living! 3D Walkthrough: Newton Village 9A Must See: Discover the unparalleled beauty of Quechee, Vermont, a destination that captivates visitors with its stunning views, endless recreational activities, and luxurious amenities. Whether you're exploring during the summer months or the winter season, a visit to Quechee is a must. Boasting a range of conveniences, Quechee provides travelers with unbeatable hospitality and the sought-after feeling of seclusion, creating an inviting atmosphere for a truly memorable vacation. Our rental home grants exclusive access to The Quechee Club, a seasonal paradise for outdoor enthusiasts. Two championship golf courses beckon in the summer, while groomed cross-country and downhill skiing trails await winter adventurers. Whether you're a fan of tennis, paddle tennis, skiing, swimming, or hiking, Quechee's diverse activities promise a memorable experience. For those seeking an invigorating workout, our state-of-the-art fitness facility, complete with indoor and outdoor pools, ensures maximum convenience. Top it all off with multiple dining choices at The Club House. For information on fees and availability, kindly contact Member Services at The Quechee Club directly. Situated in the charming small town of Quechee, our home serves as an ideal basecamp for exploring quaint New England. Adjacent to "The Prettiest Town in America" - Woodstock, VT - our home is just minutes away from galleries, unique shops, and an array of vibrant dining experiences to suit every palate. A mere 30 minutes from Killington and Pico, winter sports enthusiasts and summer adventurers alike will find skiing and mountain biking opportunities to fulfill their passions. Whatever brings you to this corner of the country, Quechee stands ready to extend a warm and welcoming embrace. Come, experience the best of what Quechee has to offer! Please pay close attention to following the house rules. Non compliance could result in sizable fines. - All guests staying at an Quechee Lakes Rentals by Portoro (Portoro Homes) are required to sign (esignature) a rental agreement and complete identity registration. - Age restrictions apply. Reservation holder must be 25 years of age. - Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Quechee Lakes Rentals by Portoro directly. - Known damages incurred during your stay must be reported to the property manager immediately. - Before check in, we will send you detailed directions to ensure a seamless arrival. - Check-in time is 3:00 p.m. Check-out time is 10:00 a.m. - We cannot guarantee early check ins or late checkouts. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night. - Some homes have cameras for external monitoring only. - In the State of Vermont and in Windsor County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. - There is no guard around the pools. - Use at your own risk. - This is a No Pets property. A daily rate fee of $150.00 will apply for violations and you may be asked to vacate the premises with no refund at the discretion of the Host. - This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host.

Walking distance to the base lodge this post and beam quintessential ski lodge boasts 5 bedrooms, 4 baths, 2 living rooms, a dining room, an outdoor deck (seasonal), a sauna and full laundry. Nestled into a hill and surrounded by a peaceful brook you are welcomed into a very private, quiet setting.In addition to being minutes away from the resort, HomeOkemo is less than 5 minutes away from downtown Ludlow, VT where you can enjoy dining and shopping at your leisure. Your home away from home!Pet Policy: 1 Dog under 50 lbs will be allowed with a $250 pet fee *Shorter 3-night minimum stays available outside of Peak Ski Season. Message for detailsMaster Bedroom: King BedThird Floor Bedroom: Queen BedMain Floor Bedroom: Queen Bed Bunk Room #1: 4 twin beds (two bunked beds)Bunk Room #2: Bunked beds Double below, Twin on top Lower Level Living Room: Sectional pull out sofa bed: Double bed About pets:Pets allowed: dogs less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 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.

Welcome to your luxurious Green Mountain Getaway! This home has been fully renovated from top to bottom, offering a fresh and modern experience while retaining its cozy charm. Perfect for large groups, the home comfortably sleeps 18 guests across 8 spacious bedrooms and 4 full bathrooms. Whether you're planning a family reunion, a gathering of friends, a corporate retreat or a group vacation, this home has everything you need for a memorable stay.~About the Getaway~8BR|4 Bath|Hot Tub| ½ mile to Okemo| On Shuttle Route | Walk Downtown|Sleeps 18|King Bed• 8 bedrooms:Bedroom 1: 1 Queen bedBedroom 2: 1 Queen bedBedroom 3: 1 Queen bedBedroom 4: 3 Twin bedsBedroom 5: 1 Queen bedBedroom 6: 1 KING bedBedroom 7: 1 Queen bed and 1 TwinBedroom 8: 1 Queen bed• 4 full bathrooms• Ski Shuttle stops right outside our door• Fresh linens, bathmats, hand towels and dishtowels provided• Kitchen – fully stocked with 2 dishwashers, Stove plpus wall oven, Fridge and Microwave• Coffee maker and Keurig, toaster, blender• Private hot tub • Fireplace• Bubble Hockey• Shuffleboard Table• BBQ grill• In-home washer + dryer• Heating• 2 very large window air conditioners to cool common areas• Ceiling fans in all bedrooms and fans are provided for bedrooms• Games and Books• 2 Smart TVs• Blackout shades• Free parking for 6-7 cars• EV charger~Experience Overview ~• Amazing downtown location and just ½ mile to Okemo Mountain• Free Ski Shuttle stops hourly outside our door• Backyard hot tub + grill area• Walkable to local coffee + restaurants +bars• Great for groups or extended stays• High-speed Wi-Fi + dedicated workspace~Nearby Things to Do ~Ludlow, Vermont, is an ideal destination for those seeking ski and adventure vacations, offering a variety of outdoor activities. Explore the stunning natural beauty of nearby national parks, serene lakes, and majestic mountains. With options for outdoor enthusiasts and culture seekers alike, Ludlow provides a scenic backdrop for memorable experiences, whether you're traveling solo, with family, or in a group.Okemo Mountain ⎯▹ 2 min drive or take shuttle to mountain hourly in winterFabulous mountain to Ski or Snowboard. Great for all ages. Tubing park and Mountain CoasterLudlow Village ⎯▹ 3 min walkWalk charming streets to discover explore bookshops, bakeries, restaurants, shops and parksLake Rescue ⎯▹ 8 min drive The scenic views and outdoor activities make it an ideal spot for relaxation and adventure.Fox Run Golf Course ⎯▹ 7 min driveAmazing Golf CourseButtermilk Falls ⎯▹ 7 min driveHike and explore the stunning waterfallCamp Plymouth State Park ⎯▹ 10 min driveBeautiful beach with small boat rentals provide perfect way to explore the LakesWeston Playhouse ⎯▹ 20 min driveExperience this renowned theater program in nearby Weston~Nearby Dining ~Hatchery (Breakfast & Lunch) ⎯▹ 5 min walkBlue Duck Deli (Lunch) ⎯▹ 5 min walkJohnny’s Kitchen (Lunch) ⎯▹ 5 min walkBig Pops (Breakfast & Lunch) ⎯▹ 3 min driveKillarney’s (Lunch & Dinner) ⎯▹ 10 min walkHomestyle Hotel (Dinner) ⎯▹ 10 min walkDowntown Grocery (Dinner) ⎯▹ 10 min walkStemwinder (Dinner) ⎯▹ 10 min walkThe Loft (Lunch & Dinner) ⎯▹ 5 min driveLittle Mexico (Lunch & Dinner) ⎯▹ 3 min driveGoodman’s American Pie (Lunch & Dinner) ⎯▹ 3 min walk~FAQs ~➤ Can I work remotely here?Yes—FAST WIFI and a solid work setup.➤ Are dogs allowed?Absolutely—furry friends are welcome with a fee. Restrictions apply.➤ What should we know about the layout?Driveway fits 6-7 cars.➤ Is there a hot tub?Yep—fully private, great for evenings under the stars.➤ What is the weather like in the winter?In the winter, there will be snow, ice, and occasional snowstorms. We recommend driving a vehicle with AWD or 4WD. Please drive with caution and be prepared with regards to the ability of your vehicle to drive in the snow. This home is located on a flat street:)➤ Will we see any wildlife?You may see wildlife including deer, coyotes, foxes, and bears. Please be mindful of your surroundings and leaving out food and trash.➤ Is there air conditioning?There are two very large window units to cool all common areas of the house on the first and second floors. Nights are typically much cooler and there are ceiling fans in all bedrooms and window fans are provided for all bedrooms for your comfort.~Meet Your Hosts~We love Ludlow and our wonderful guests who come to visit! Need anything at all? We are just a text away!Your hosts,—Jeff and DianeAbout pets:Pets allowed: dogs less than 20 lbs per pet (limit one pet total).About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:No saturday check in/out in winter.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About events:No events allowed.