Windsor County

Boutique Hotels in Windsor County

Enter your dates to find boutique hotels in Windsor County that offer unique style and charm.

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Top Boutique Hotels Windsor County

Discover the best boutique hotels in Windsor County, celebrated for their unique style and personality.
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Hotels in Windsor County
Featured facilities: Pool, Bar, Restaurant
Great
100 reviews
9.0/10
1 night
From €165
Check availability
99+
Hotels in Windsor County
Featured facilities: Pool, Bar, Restaurant
Amazing
99 reviews
9.4/10
1 night
From €359
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72
Hotels in Windsor County
Featured facilities: Restaurant
Amazing
98 reviews
9.6/10
1 night
From €122
Check availability
31
Hotels in Windsor County
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.
Outstanding
70 reviews
9.8/10
1 night
From €164
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99+
Hotels in Windsor County
Featured facilities: Pool, Bar, Restaurant
Great
101 reviews
9.2/10
1 night
From €132
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22
Hotels in Windsor County
Charming Vermont cottage, just up the road from Silver Lake and the Barnard General Store. Bright, warm, and welcoming, this home has all the comfort you need to make it feel like home away from home.This home is private and secluded for your getaway and also close to all Vermont has to offer including Woodstock, Killington, Montpelier, and Burlington.We love this space and have taken time and care into making sure you love it just as much. We have filled the space with items that have brought us joy from the butcher block that made its way from California 30 years ago, to the radio that a friend gave us, to the quilts handmade by the host, and all the way down to the little bits and pieces we have picked up at yard sales and thrift stores throughout our lives. We hope you feel the warmth and comfort as your relax in to your stay.The home is open concept with a large space downstairs for kitchen, dining, and living areas and a large loft like space upstairs that includes two beds, separated by a lounging area.The home is heated with radiant floor heating so your feet never get cold. In the evenings, for a little extra warmth, cozy up next to the gas fireplace.There is a great office space with beautiful views of the garden. It gets nice light and paired with our super fast wifi (100mbps), it makes this home a perfect place to work from away.In true Vermont fashion, there are no window coverings or shades. Not to worry, this home is on 7 acres, set back from the road, and the neighbors are out of sight.Located on the North Rd, this home is surrounded by stunning views and farmland, in the heart of Barnard.Head on down to the General Store for their World Famous Pancakes or a scoop of ice cream before heading off on any of the many outdoor adventures this area has to offer.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Outstanding
8 reviews
10/10
Check availability
16
Hotels in Windsor County
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 12.3 mi (19.9 km) from Quechee Gorge Bridge. 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.
Outstanding
9 reviews
10/10
1 night
From €185
Check availability
61
Hotels in Windsor County
With a stay at The Weston in Weston, you'll be within a 15-minute walk of Weston Playhouse and Green Mountain National Forest. This luxury guesthouse is 4.1 mi (6.5 km) from Weston Priory and 5.7 mi (9.1 km) from Lowell Lake State Park. Pamper yourself with a visit to the spa, which offers massages and facials. This guesthouse also features complimentary wireless internet access and concierge services. At The Weston, enjoy a satisfying meal at the restaurant. Mingle with other guests at the complimentary reception, held daily. Wrap up your day with a drink at the bar/lounge. Full breakfasts are available daily from 7:30 AM to 9:30 AM for a fee. Featured amenities include luggage storage and coffee/tea in a common area. Free self parking is available onsite. Make yourself at home in one of the 9 air-conditioned rooms featuring iPads. Your memory foam bed comes with premium bedding. Complimentary wireless internet access is available to keep you connected. Private bathrooms have complimentary toiletries and hair dryers.
Outstanding
5 reviews
10/10
1 night
From €345
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36
Hotels in Windsor County
With a stay at this cottage in Ludlow, you'll be within a 10-minute drive of Okemo Mountain Resort and Dorsey Park. This cottage is 1.2 mi (2 km) from Blue Lot and 1.6 mi (2.5 km) from Red Lot. Make use of convenient amenities, which include complimentary wireless internet access and an arcade/game room. Free self parking is available onsite. Make yourself comfortable in this air-conditioned cottage, which features a fireplace. There's a private balcony. A kitchen is outfitted with an oven, a stovetop, and a microwave. Conveniences include a coffee/tea maker and a dryer, and you can also request a crib/infant bed (complimentary).
Outstanding
10/10
1 night
From €1,015
Check availability
87
Hotels in Windsor County
With a stay at The Woodstocker B&B in Woodstock, you'll be within a 10-minute walk of Woodstock Town Hall Theatre and Middle Covered Bridge. This bed & breakfast is 14.5 mi (23.3 km) from Killington Resort and 0.5 mi (0.8 km) from Red Wagon Toy Company. Take advantage of recreation opportunities such as a sauna or take in the view from a terrace and a garden. Grab a bite from the snack bar/deli serving guests of The Woodstocker B&B. A complimentary cooked-to-order breakfast is served daily from 8 AM to 10 AM. Free self parking is available onsite. Make yourself at home in one of the 9 air-conditioned rooms featuring flat-screen televisions. Private bathrooms with showers feature complimentary toiletries and hair dryers. Housekeeping is provided daily, and irons/ironing boards can be requested.
Outstanding
40 reviews
9.8/10
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FAQs

What is the average price of a hotel in Windsor County for this weekend?

According to the latest 12-month data from Trip.com, the average price for a 3-star hotel in Windsor County this weekend is €255 per night. For a 4-star hotel, the average cost is €552 per night. If you're looking for a luxury experience, 5-star hotels in Windsor County this weekend typically cost €807 per night.

How much do hotels in Windsor County cost per night during weekdays?

Based on the latest 12-month data from Trip.com, the average price for a 3-star hotel in Windsor County during weekdays is €237 per night. For a 4-star hotel, you can expect to pay around €488 per night. If you're seeking a luxury stay, 5-star hotels in Windsor County generally cost €626 per night on weekdays.

What are the best places to stay in Windsor County?

Some of the best places to stay in Windsor County are near popular attractions like AT trailhead Woodstock VT, offering easy access to key sights and amenities.

Where can I find the best hotel discounts in Windsor County?

Trip.com provides various promotions and discounts for users all year round. You can check the promotions page to see what promotions are available on Trip.com.