Windsor County

Boutique Hotels in Windsor County

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

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Top Boutique Hotels in Windsor County

Browse top boutique hotels in Windsor County known for their distinct style and personality.
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Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)
Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)Cozy 1 king bed Apt Minutes to Okemo (Pet Friendly)
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
3 reviews
10.0/10
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Thanksgiving Available - 8 Br, 4 BTH, 1/2 mi to Okemo, Hot Tub, on Shuttle, King
Thanksgiving Available - 8 Br, 4 BTH, 1/2 mi to Okemo, Hot Tub, on Shuttle, KingThanksgiving Available - 8 Br, 4 BTH, 1/2 mi to Okemo, Hot Tub, on Shuttle, KingThanksgiving Available - 8 Br, 4 BTH, 1/2 mi to Okemo, Hot Tub, on Shuttle, KingThanksgiving Available - 8 Br, 4 BTH, 1/2 mi to Okemo, Hot Tub, on Shuttle, KingThanksgiving Available - 8 Br, 4 BTH, 1/2 mi to Okemo, Hot Tub, on Shuttle, KingThanksgiving Available - 8 Br, 4 BTH, 1/2 mi to Okemo, Hot Tub, on Shuttle, King
26
Hotels in Windsor County
Welcome to your luxurious Vermont 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.Located in a prime downtown location, this home is conveniently situated on the ski shuttle route to Okemo Mountain, making it ideal for skiing and snowboarding enthusiasts. When you're not hitting the slopes, take advantage of the many nearby restaurants, shops, and attractions.After a day of adventure, unwind in one of the two large living rooms, each offering plenty of space to relax. Cozy up by the fireplace or enjoy some friendly competition with a game of shuffleboard. The home is also stocked with books and games, perfect for a cozy night in. For those needing to catch up on work, the house offers a dedicated workspace, ensuring you can be productive during your stay.The fully equipped modern kitchen features granite countertops, stainless steel appliances, a stove and wall oven, and two dishwashers for easy cleanup. The open-plan kitchen and dining room has seating for 12 at the dining table and 4 at the kitchen island, perfect for shared meals and gatherings.Step outside onto the deck and enjoy the private hot tub and gas firepit—ideal for relaxing under the stars. The house is also handicap accessible, ensuring comfort for all guests. Plus, if you're driving an electric vehicle, we’ve got you covered with a dedicated EV charging station.For entertainment, the home is equipped with Wi-Fi and smart TVs throughout, so you can stream your favorite shows and stay connected.This spacious and beautifully designed home is perfect for large groups looking to experience the best of Vermont's outdoors while enjoying the comfort and convenience of a modern retreat.Amenities:• Completely Renovated from Top to Bottom• Sleeps 18 Guests• 8 Bedrooms, perfect for large groups• 4 Full Bathrooms• Two Spacious Living Rooms with Fireplace and Shuffleboard• Dedicated Workspace for remote work• Fully Equipped Modern Kitchen with stove, wall oven, and 2 dishwashers• Granite Countertops and Stainless Steel Appliances• Seating for 12 in the dining room and 4 at the kitchen island• Hot Tub and Gas Firepit on the deck• Handicap Accessible• Wi-Fi and Smart TVs throughout• EV Charging Station• Books and Games for cozy nights in• Open-Plan Layout perfect for gatheringsLocation:This home is ideally located near Okemo Mountain, with easy access to skiing, snowboarding, and other outdoor activities. It's situated on the ski shuttle route, making it incredibly convenient to get to the mountain. The property also enjoys a great downtown location, putting you close to local shops, restaurants, and attractions.Whether you're seeking adventure or relaxation, this Vermont retreat offers the best of both worlds. Come experience the comfort, style, and natural beauty of this incredible home!About 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 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.
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Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.
Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.Ski in/Ski out nicely updated 2 BR condo on Okemo Mountain ski trails.
21
Hotels in Windsor County
Featured facilities: Swimming Pool
Outstanding
20 reviews
10.0/10
Check Availability
Windsor County
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Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
Modern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from OkemoModern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from OkemoModern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from OkemoModern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from OkemoModern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from OkemoModern 7Bd/3Ba Mountain Chalet w/ Hot tub, 3 minutes from Okemo
22
Hotels in Windsor County
Completely renovated 7 bedroom, 3 bathroom modern mountain house, located in Ludlow. Outdoor deck with BBQ, hot tub, across the street from the mountain shuttle. All rooms with smart Tvs, game room with billiards and board games, large chefs kitchen with dining room and kitchen island. Mudroom at back entry.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About customRules:Please turn the thermostats to 62° before check out.Please make sure the hot tub is covered after each use,Please throw all the garbage in the outside bin and make sure that lid is closed.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
10.0/10
Check Availability
4 B.R. Ski Chalet: Minutes to Slopes
4 B.R. Ski Chalet: Minutes to Slopes4 B.R. Ski Chalet: Minutes to Slopes4 B.R. Ski Chalet: Minutes to Slopes4 B.R. Ski Chalet: Minutes to Slopes4 B.R. Ski Chalet: Minutes to Slopes4 B.R. Ski Chalet: Minutes to Slopes
32
Hotels in Windsor County
Just a 6-minute drive from Okemo’s base lodge, our cozy chalet offers the perfect escape into a serene forest.Step into our spacious mudroom to shed your gear and head into the bright, open-concept living area. Relax by the crackling wood-burning fireplace, or gather with loved ones in the dining area. The fully-equipped kitchen is perfect for preparing home-cooked meals.When you’re ready for some fun, head downstairs to the entertainment level. Challenge friends to a game of ping pong, basketball arcade, or skee ball, or unwind with a movie night in the home theater.Explore the 10 wooded acres surrounding the chalet, with winding trails, babbling streams, and lush foliage. Gather around the fire pit for cozy evenings under the stars.NOTE: Our driveway is sloped and while we have snow removal, we recommend you have a 4WD vehicle to access the chalet.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 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
10.0/10
Check Availability
Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/D
Okemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/DOkemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/DOkemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/DOkemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/DOkemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/DOkemo Ski in-Ski out @ Winterplace, 3 bdr, 2 ba Condo with Pool, Hot Tub, W/D
25
Hotels in Windsor County
Featured facilities: Swimming Pool
Outstanding
9.8/10
Check Availability
Ski Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at Winterplace
Ski Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at WinterplaceSki Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at WinterplaceSki Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at WinterplaceSki Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at WinterplaceSki Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at WinterplaceSki Okemo! Walk to the slopes from your modern 2 bed/2 bath condo at Winterplace
11
Hotels in Windsor County
Featured facilities: Swimming Pool
Outstanding
2 reviews
9.8/10
Check Availability
Valhalla!!
Valhalla!!Valhalla!!Valhalla!!Valhalla!!Valhalla!!Valhalla!!
31
Hotels in Windsor County
Welcome to Valhalla on Lake Rescue! We are a lovely four season home with plenty of options right outside our doorstep. Jump on a kayak or throw your hiking shoes on and explore Okemo Mountain and the gorgeous surrounding area. We are just 5 minutes from Okemo and 35 minutes from Killington, Bromley and Magic ski mountains. Our newly renovated home is a 7 minute drive to downtown Ludlow with great restaurants and shops.The spaceOur home is full of custom details to make guests feel comfortable. The first floor is an open concept that makes hanging out and cooking cozy and comfortable. The foyer has custom built-in and benches to make winter undressing and dressing easy. All new appliances in the kitchen are stainless steel. Stove is gas. The kitchen is equipped with everything you need to make great meals. The game area is adjacent to the dining area and both have stunning views of the beautiful lake. The game area has games for all ages to enjoy. The living room has a brand new smart TV, high speed Wi-Fi and Nest thermostat.BedroomsAll 4 bedrooms are located upstairs. The sleeping configuration is as follows: 2 queen rooms with memory foam mattresses, 1 twin over full bunk bed with a trundle bed and 1 twin over full bunk bed.There are two folding cribs. One is a standard size and the other crib is a mini crib.Bathrooms1 full bathroom on first floor with tub and shower1 full bathroom on second floor with shower only. This bathroom contains full sized washer and dryer for your use.The bathrooms are equipped with Terra Pure toiletries for your convenienceOutdoor spaceThe deck wraps around 3 quarters of the house with 3 separate stairs with gates. By the lake there is dock to enjoy fishing from, morning cup of coffee or evening cocktail on and enjoy the beautiful lake views.There is a firepit with comfortable seating around it. There are 4 adult kayaks; 2 of which are ocean kayaks, 2 childrens kayaks and 1 rowboat are for your use.Our wish is that you are able to relax and unwind during your stay at Vahalla and find some peace and tranquility to take with you.Guest accessParking for our house is right in front the house.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: 21.About events:No events allowed.
Outstanding
9.8/10
Check Availability
Vermont Trailside Getaway
Vermont Trailside GetawayVermont Trailside GetawayVermont Trailside GetawayVermont Trailside GetawayVermont Trailside GetawayVermont Trailside Getaway
35
Hotels in Windsor County
Featured facilities: Swimming Pool
Outstanding
15 reviews
9.8/10
Check Availability
Ski in Ski out! top of the  A quad chairlift
Ski in Ski out! top of the  A quad chairliftSki in Ski out! top of the  A quad chairliftSki in Ski out! top of the  A quad chairliftSki in Ski out! top of the  A quad chairliftSki in Ski out! top of the  A quad chairliftSki in Ski out! top of the  A quad chairlift
22
Hotels in Windsor County
2 Bed 2 Bath. Pull out sleep sofa. Sleeps 4 Adults and 4 children.Located at the top of the chairlift with a balcony overlooking the mountain. Watch the skiers from your deck! Indoor heated communal pool adjacent to the tennis court. Fast internet - convenient!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 allowed: in designated areas.About minBookingAge:Minimum age to rent: 34.About events:No events allowed.
Outstanding
5 reviews
9.8/10
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Frequently Asked Questions

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: SAR 1,814
4-star hotels: SAR 1,889
5-star hotels: SAR 2,720

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: SAR 1,454
4-star hotels: SAR 1,838
5-star hotels: SAR 2,218