Vacation rentals in Windsor County

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Top-rated vacation rentals in Windsor County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A hot tub is depicted with glowing blue lights illuminating the water and steam rising into the night air. The structure above is part of a covered porch, providing an inviting area for relaxation outside.

Home in Cavendish

4.98 out of 5 average rating, 48 reviews

Okemo <12 min Game room~Hot tub~Fire pit~Mtn Views

The Red Ranch is a hop, skip and jump away from Okemo Mountain Ski Resort. < 12 min to Ludlow, Okemo MTN, nearby lakes and VAST trails. This thoughtfully remodeled farmhouse ranch sits on 4 acres, with HOT TUB. Enjoy the peace and tranquility of nature just beyond your front door. Listen to the sounds of nearby streams roaring in the near distance as you sip on your morning coffee from our enormous, covered porch. This home boasts designer touches with serious attention to details throughout.

Guest favorite

A spacious backyard is shown, featuring a well-maintained lawn surrounded by lush greenery. A deck is visible, along with a hot tub and a fire pit seated with outdoor chairs. Scenic mountain views can be seen in the distance under a blue sky.

Home in Rutland

4.89 out of 5 average rating, 184 reviews

Killington/Okemo, 7p Hot tub, Mtn.views, Spacious!

Mid week deals! Killington Mnt-20min drive, Lake Bomoseen-20min, Pico Mnt-15min Okemo-30min, Downtown Rutland-5min (bars/dining/shopping) Mnt Top Inn-18min, Hiking-10 min. , Neighborhood pool with tennis courts, basketball courts, playground. Beautiful mountain views, peaceful brook on 1+ acre property. Spacious home with hot tub, AC, firepit, fooseball table, grill, deck, patio, screenroom, 2 kitchens, 2 living rooms, washer/drier, fully stocked kitchens. Very fast wifi/netflix/youtubeTV.

Superhost

A serene outdoor space features two Adirondack chairs positioned around a fire pit, surrounded by lush green grass and a backdrop of dense trees. The calming natural setting invites relaxation and outdoor gatherings.

Cottage in Mendon

5 out of 5 average rating, 5 reviews

The Mendon Cottage: Cozy Home. Killington / Pico

Recently renovated 2BR/2BA cottage in Mendon, VT, near Pico & Killington Ski Resorts, & Rutland. Sleeps 6: 1BR w/ queen & ensuite, 2nd BR w/ 2 double beds. Additional BA, laundry room, living room w/ smart TV, fully equipped kitchen & dining area. High-speed WiFi, mini splits for heat/AC, front & back decks, BBQ grill. All new furnishings offer modern comfort & rustic charm. Ideal for skiing, exploring, or relaxing in the mountains. Perfect base for your VT adventure! Discounted ski rentals.

Guest favorite

A modern walk-in shower is enclosed with glass doors, featuring a colorful tiled floor and ambient lighting along the ceiling. The showerhead and handheld sprayer are positioned on the wall, with corner shelves displaying various toiletries.

Vacation home in Rutland

4.93 out of 5 average rating, 61 reviews

very nice vacation rental 20 min from Killington

Very nice vacation rental 20min from Killington and Pico. 30min from Okemo. 20 minutes from Chittenden Reservoir. 20 minutes from Mount Tabor. 20 minutes from Lake Bomoseen. 15 minutes from Proctor. 10 minutes from Rutland Airport. Private code lock entrance to a full apartment with no shared spaces. Full kitchen, walk in shower, washer dryer, two bedrooms with three queen size beds and Roku TV. Pull out couch in living room plus additional cots. Right off rt 7 on two acres in Rutland.

Superhost

Cabin in Bridgewater

4.91 out of 5 average rating, 100 reviews

100 Acres Views & Creek near Woodstock/Killington

You will leave the demands of your busy lifestyle behind when you vacation on our 100+ acre 4 BR 2 BA cabin property with a babbling crystal clear mountain creek. Place your beach chair in the creek, relax with your favorite book for Best Spa Experience Ever! Large open covered porch with porch swing seating to enjoy the expansive mountain views, listen to the leaves rustle and the stream running in the distance. Miles of hiking & biking trails, skiing, restaurants and more nearby.

Guest favorite

A screened-in porch features colorful seating, including blue and green chairs, surrounding a small table. Natural light filters through large windows, revealing views of the lake and surrounding greenery. String lights hang from the ceiling, adding a cozy touch.

Cabin in Plymouth

4.93 out of 5 average rating, 14 reviews

Poppy's Cabin~Dogs~HotTub~FirePlace&Pit~Okemo

Rent a "room" at an inn or rent this private B & B cottage. Romantic Retreat~Rest & relax! Unique tranquil getaway. Exclusive~A Bed & Breakfast Cottage for 2 adults. 1 BR & 2 BA. Rustic charm, generous modern amenities. King bed, 2 bathrooms, fine linens, living/dining area, galley kitchen, fireplace, hot tub, outdoor shower*, porch, fire pit, canoe*, & dog friendly! Killington&Okemo15minutesWoodstock 30 minutes-Ludlow 10 minutes Overlooks Lake Amherst. *Some features are seasonal.

Top guest favorite

A modern cabin is situated among snow-covered trees, showcasing large windows that reflect the evening sky. The triangular roofline and dark exterior contrast with the white snow, while a cozy glow emanates from within.

Home in Peru

5 out of 5 average rating, 10 reviews

Highland Haus: stunning ski getaway with hot tub

Welcome to The Highland Haus! A brand new, custom luxury escape central to dining, shopping, and four Vermont ski resorts. Overlooking several mountain ranges, this high-end getaway offers an unparalleled experience in the heart of the Green Mountains: breathtaking views, three bedrooms 3.5 bathrooms, open concept living and dining rooms, outdoor dining and lounge deck, hot tub, modern decor and amenities. Come enjoy Vermont at its finest! Pets welcome with a $100 pet fee.

Top guest favorite

An indoor jacuzzi room features ample natural light streaming through multiple windows. The room is surrounded by wooden paneling, enhancing the cozy ambiance. A spacious, circular jacuzzi is positioned in the center, complemented by a built-in bench along one wall.

Cabin in Killington

4.97 out of 5 average rating, 30 reviews

Luxury Ski Cabin, 2 bedrooms, den & 3 bathrooms

This luxury residence on Killington Mountain is a 400-yard walk to the closest ski trail or a short 5-minute drive to the principal ski bases, along with the resort's array of bars, eateries, and retail outlets. It features an indoor jacuzzi, a spacious living/kitchen area bathed in natural light. A variety of summer pursuits, including golf, hiking, mountain biking, and canoeing, are conveniently accessible within minutes from the home. Plus, the property welcomes pets.

Guest favorite

A private Jacuzzi hot tub sits on a gravel patio, surrounded by stone pathways and landscaping. The hot tub is positioned against a backdrop of lush foliage, offering a serene outdoor relaxation area. Nearby, partial views of a road and grass are visible.

Home in Plymouth

4.95 out of 5 average rating, 251 reviews

Top of the World! Jacuzzi! Private Hiking Trails!

Welcome to one of the most unique "retreats" in Vermont! Located on top of a private mountain, beautiful 100 mile views of the White Mountains. Ideally located between Killington (7 miles) and Okemo resorts, near Woodstock and Long Trail Brewery. Relax in the Jacuzzi hot tub while enjoying the views and stars. Private hiking trails, waterfalls, with trail maps! 7 miles to the beach at Camp Plymouth State Park. Secluded yet close to everything. New ventilation system.

Guest favorite

The kitchen features a modern design with white cabinetry and a wooden countertop. Two windows allow natural light to brighten the space, while stainless steel appliances, including an oven, are positioned along the walls. A sink is centrally located, enhancing functionality.

Home in Cavendish

4.96 out of 5 average rating, 26 reviews

Charming New England Cape- 10 Minutes from Okemo!

Relax with the whole family, or friends at this peaceful place to stay. Close to many local ski resorts, hiking trails, trophy fishing in the Black River off Route 131! Close to Ludlow And Historic Windsor and Woodstock VT! Only a 10 minute drive to Okemo Mountain and Jackson Gore! 30 Minutes to Killington Mountain and Magic Mountain 40 Minutes to Bromley Mountain Accessible to the natural beauty of Vermont!

Superhost

A spacious family room features a large, light-colored couch and a cozy area rug. A stone fireplace serves as the focal point, surrounded by large windows that provide a view of the wooded surroundings. A coffee table and an armchair enhance the inviting atmosphere.

Home in Hartford

4.8 out of 5 average rating, 10 reviews

Pet-Friendly, Mountainside Home | Treetop Lodge

Our vacation home is the ultimate getaway for families and groups looking to indulge in luxurious comfort and endless entertainment options. Book your stay today and experience the beauty and tranquility of this truly remarkable property. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *Pet Friendly, fee applies per pet. *Includes Quechee Club Access

Top guest favorite

A spacious deck features four wooden Adirondack chairs arranged around a small table, inviting relaxation. The lush green backyard is visible, complemented by trees and an open area, enhancing the sense of privacy and tranquility in the natural surroundings.

Chalet in Mount Holly

5 out of 5 average rating, 59 reviews

Cozy chalet mins from Okemo & VAST.

Come enjoy some time in our cozy & relaxing 3-bedroom, 2-bath home. If you prefer a winter or summer getaway, all the options are available. Minutes from all activities and restaurants. Enjoy the nearby hiking and biking trails, Buttermilk Falls, Jackson Gore and Okemo SP. Property located opposite mountain traffic. Hang a left on 103 when leaving JG/ Okemo Main Rd.

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What guests are saying

Beartopia- hot tub, views, 2 primary suites!

5 out of 5 average rating, 32 reviews1 month ago

We loved our stay here, I have only great things to say. The house was perfect for our group of 8. The access to the mountain and to town is super easy, and everything about the house is as good as it looks in the pictures. Dan/Holly had great communication leading up to and throughout our trip. I’d highly recommend staying here.

Home in Killington

What guests are saying

Ski-in Ski-Out Cozy Mountainside Condo

4.88 out of 5 average rating, 57 reviews4 months ago

Everything was lovely. The house was warm and cozy. We so enjoyed gathering around the fireplace in the evening. Just 10 minutes away the kids went skiing at the Quechee Ski Resort which they liked and was so accessible. Last but not least our host Robin was so nice. She answered all our questions immediately. And was very pleasant.

Townhouse in Hartford

What guests are saying

Private post & beam log cabin on Macintosh Pond.

4.8 out of 5 average rating, 15 reviews3 months ago

It was perfect for what we wanted! We were giving Grandma an 80th Hallmark Experience. A lot of what we did was in Woodstock and it was a noce 30 min ride to the town, but for us very convenient. We had a family of 14 and we played games in ythe main living room all together. The downstairs was perfect for our older kids to hang out in!

Cabin in Barnard

What guests are saying

Gigi and Pops' Secret Cabin

5 out of 5 average rating, 55 reviews3 weeks ago

Wow! What a spot! Not only is the house amazing, the property is also amazing! The location is 10 min from town and 10 minutes to the mountain! The house was very clean and the owners thought of everything that you would need! We brought our 4 young kids and between the fort outside and the playroom, they had the best time! We will definitely be back!

Home in Chittenden

What guests are saying

The Carol

5 out of 5 average rating, 22 reviews1 month ago

The Carol is a stunning and beautifully decorated historic home that was the perfect getaway for our ski trip!!! We stayed one night but wish we had stayed longer! It is located only 10 mins from Okemo which was perfect. The beds were super comfy and the bathroom and kitchen were stocked with everything we needed. Sarah was super helpful and responsive to everything and provided tons of recommendations to make our stay worthwhile. Would 100% recommend this place to anyone looking to ski Okemo!

Home in Cavendish

What guests are saying

Hilltop 4-BR Retreat 8-min to Okemo Mountain

5 out of 5 average rating, 8 reviews3 months ago

Stayed here with friends and family to snowboard at Okemo. Unreal Mountain View’s from the living room! Perfect location right down the road less than 10 minutes which was a game changer after a long tiring day. This place was better than I imagined and perfect for us. Three entry ways the mud room was great to drop all the gear. Kitchen had everything we could have wanted, probably the best and most thoughtful Airbnb. We cooked a lot and we didn’t feel like we were missing anything we needed! Plenty of books and board games.. scrabble and chess won the favorites of our group. Water got hot quick for showers. Fireplace really warms the place up quick. Host left a personalized handwritten note to us and messaged us during our stay if we needed anything. We would all happily make another trip and come back! If I had to say one thing it would be that some of the beds and pillows weren’t as comfortable but it wasn’t a deal breaker! Place exceeded our expectations!!

Home in Ludlow

What guests are saying

Luxury Modern Cabin near Okemo & Killington

5 out of 5 average rating, 16 reviews1 month ago

Stephanie was an Incredible host! The listing matched her description and the property looked even better upon checking in. Stephanie maintains this property really well and I couldn’t have felt any more at home. The home was clean and had a perfect cozy feeling to it. In addition, this was really close to the mountain, which made the getaway even better. I enjoyed the privacy and waking up to a nice snow dusting before my trip to the mountain. I highly suggested staying at Stephanie’s property if you’re looking for a quick getaway. I certainly will be looking to book again soon. Thank you Stephanie!

Home in Plymouth

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