Windsor County

Boutique Hotels in Windsor County

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Top Boutique Hotels in Windsor County

Browse top boutique hotels in Windsor County known for their distinct style and personality.
Most Booked
Lowest price
Closest to downtown
Highest Rated
99+
Hotels in Windsor County
Featured facilities: Swimming Pool, Bar, Restaurant
Great
101 reviews
9.2/10
1 night
From RUB 15,542
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99+
Hotels in Windsor County
Featured facilities: Swimming Pool, Bar, Restaurant
Amazing
99 reviews
9.4/10
1 night
From RUB 31,370
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72
Hotels in Windsor County
Featured facilities: Restaurant
Amazing
100 reviews
9.6/10
1 night
From RUB 11,117
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99+
Hotels in Windsor County
Featured facilities: Swimming Pool, Bar, Restaurant
Great
100 reviews
9.0/10
1 night
From RUB 11,989
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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 RUB 14,544
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60
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 RUB 35,140
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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 7.2 mi (11.7 km) from Green Mountain National Forest and 10.1 mi (16.2 km) from Killington 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.
Outstanding
10 reviews
10/10
1 night
From RUB 16,424
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45
Hotels in Windsor County
Gather around the fireplace in the living room with massive wall to wall windows or relax on the second story deck under the stars. Take in spectacular sunset and mountain views from a beautifully renovated three story home. Nestled privately on 4 wooded acres just 15 minutes from Okemo, offering the quintessential VT experience in a chic and charming chalet. With 3 bedrooms, 2.5 baths, and brand new kitchen, this is our family's vacation home and we look forward to sharing it with you.The spaceIt's all about the views at this luxurious, recently renovated from top to bottom, three story home. Nestled on over 4 acres of wooded land, this gorgeous and chis retreat faces west so you can experience some of the most spectacular sunsets in Vermont. You will also enjoy spectacular views of the Green Mountains from nearly every room on the top two floors and from the deck.In a prime location, just minutes from Weston center (with its Vermont Country Store, not to be missed), 15 minutes to ski OKEMO and the town of Ludlow, 15 min to Fox Run Golf Club and fishing, kayaking or paddle boarding on Echo lake.The whole house has been completely gutted and rebuilt, designed to offer the true VT experience. From the inviting living area, which features a wood burning fireplace, cathedral ceilings and wall to wall windows and sliders that invite the outdoor in, to the custom made kitchen with custom made hood (reclaimed wood from an old VT barn), natural stone backsplash, high end appliances and center island. The kitchen is equipped with everything you need to cook a nice dinner or breakfast. Open space between the living room, dining room (sitting up to 8 guests and with massive windows overlooking the mountains), and kitchen. The family room, on the same level, is cozy , has a pull out queen-size couch, and Smart TV. Much thought has been put into designing the half bath on this level, with a custom-made vanity (from an antique dresser) to custom-made light fixtures and bath fixtures. The first floor welcomes you with a spacious hallway, 2 bedrooms, and a large bathroom (with tub and double vanity). As you walk up the 3rd floor, the views are getting better and better from the primary suite, which boasts wall to wall windows. This top floor bedroom leads to a cozy lofted living area (with a pull out couch) and a primary bathroom with shower and custom-made fixtures.Enjoy time outside on the deck either overlooking the mountains or at night, stargazing. It is truly a special place that we absolutely love and are now sharing it with you.Guest accessGuests will have access to the whole house (including washer and dryer) and yard. No access to the garageOther things to notePack and Play, books, some kids toys.About pets:No pets allowed, service animals permitted.About checkOut:Check out before 10:30 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: 21.About events:No events allowed.
Outstanding
4 reviews
10/10
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17
Hotels in Windsor County
Looking for an affordable getaway near the scenic mountains of VT? Look no further! Our cozy one-bedroom apartment is just five minutes from the center of Ludlow and Okemo. Offering an open floor plan with a king bed, kitchenette with convection oven, open living space. Perfect for those looking to explore nature while enjoying comfortable, modern amenities. Book now and enjoy this hidden space above the carriage house where you will walk up the steep Vermont staircase to a modern hideaway.About pets:Pets allowed: less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 13-17.Due to stair case we do not recommend to toddlers.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Outstanding
10/10
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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
10/10
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FAQs

What are the must-visit spots in Windsor County?

Windsor County is home to iconic landmarks such as AT trailhead Woodstock VT.

What’s the average hotel price in Windsor County this weekend?

The average prices for hotels in Windsor County this weekend are as follows:
3-star hotels: RUB 22,913
4-star hotels: RUB 53,079
5-star hotels: RUB 78,968

How much do hotels in Windsor County usually cost on weekdays?

On average, hotel prices in Windsor County on weekdays are approximately:
3-star hotels: RUB 20,092
4-star hotels: RUB 44,268
5-star hotels: RUB 58,968