Holiday rentals in Windsor County

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Top-rated holiday rentals in Windsor County

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Top guest favourite

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 favourite

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

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 favourite

Holiday 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 favourite

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 favourite

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 favourite

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 favourite

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 favourite

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

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 favourite

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.