House holiday rentals in Windsor County

4.97 out of 5 average rating, 69 reviews

Heart of Ludlow. Quaint, Cozy Home, Sleeps up to 7

PRIME SKI 🎿 LOCATION !!!! Adorable cape style home 🏠 one mile from Okemo Mountain, on the weekend/holiday shuttle line. In town, very desirable location! Restaurants, shops, + bars within 1 block from front door!! Fully equipped kitchen, spacious living room, ski apparel storage room, small deck on 2nd level perfect spot for a glass of wine while watching the sunset 🌄 over the mountain! Wi-fi, NetfIix, (no cable) Price reflects reservation for 4. After 4, there is a $25 charge per person.

4.94 out of 5 average rating, 117 reviews

Home in Killington

Cozy Private House on Killington Mtn - Hottub

Welcome to our home. This beautiful 3,000 square foot three level home comes with everything you need for a mountain vacation. We have 3 bedrooms & 3 full baths that sleep 8 comfortably. We also have a indoor gas fireplace and outdoor luxury 5 person hottub (all year). The house has three spacious levels, including a basement with foosball, ping pong and a mini gym. Just minutes drive from the the resort, K1 base, Skyeship base, as well as the local attractions. Great for families/ski groups.

4.92 out of 5 average rating, 118 reviews

Home in Mount Holly

Modern Farmhouse - 2 kings, minutes to Okemo!

Newly renovated property surrounded by picturesque mountains with views from every bedroom. Relax in our cozy 4 bedroom, 2 bath home, large enough for your whole family to come together. Sleeps 11. Dog friendly. Arcade games and firepit. Large yard. Excellent place to work remotely. Enjoy hiking, fishing, biking, kayaking, skiing & golf nearby. Explore nearby Ludlow, Woodstock, Manchester and Weston. Okemo & Jackson Gore resorts are less than 10 minutes away. Killington Mtn 30 min drive.

4.89 out of 5 average rating, 185 reviews

Home in Rutland

Spacious, Near Killington, 7p Hot tub, Mtn. views!

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.

4.99 out of 5 average rating, 145 reviews

Home in Killington

DoubleDen - AC, Hot Tub, Game Room, Fire Pit

Fantastic location on Killington Road! This interior connected duplex, offered as the entire house with 6 bedrooms, 4 baths is located at the shuttle stop, and a few minutes from the main resort base. Walk to some of the best restaurants and night clubs. Relax in large outdoor hot tub, or play with the arcade games, foosball, or pool table. Enjoy fast internet over the gigabit connection on the 75" TV (or one of several others), or go retro with the 80's VHS and console game areas downstairs.

4.99 out of 5 average rating, 90 reviews

Home in Windsor

Summer/Fall at Ascutney- Mountain cabin with views

Beautiful views and a unique setting define this stylish house on a flank of Ascutney. It has a luxurious master suite, and a bedroom with 2 twin bunk beds. Woodstock village, Okemo, Killington and Sunapee, and the Upper Valley are a quick 20 to 40 minutes. The Brownsville Butcher and Pantry and Ascutney trailheads for hiking/snowshoeing are next doors. The Harpoon Brewery, and backcountry skiing are close by too. This recently built home home offers something for everybody in all seasons.

4.91 out of 5 average rating, 295 reviews

Home in Rochester

Mountain Home ready for you!

Get away from it all in a secluded home atop a mountain in the National Forest. Home with deck and panoramic view of the Green Mountains. Idyllic in all seasons. Summer is lusciously green; fall colors seen from our deck; the magic of winter. Tons of privacy, but minutes from town. 35 min to Killington or Sugarbush; snowshoe outside your door, and x-country nearby. Snow tires or chains needed from Dec.-March. Please note that we cannot help you if your car gets stuck en route to the house.

4.96 out of 5 average rating, 102 reviews

Ludlow Village/Okemo Shuttle - Oma K's Kottage

This house comfortably accommodates 8 people and boasts a large modern kitchen, additional dining area, cozy living room and attached garage. Walking distance to pubs, restaurants and shopping. Conveniently located in Ludlow Village, Oma K's Kottage offers premier winter skiing at Okemo Mountain Resort and access to nearby lakes and river water sports in summer. Whether it’s hiking, cycling, golf or fly-fishing, this ideal location has something for everyone. Come stay and play at Oma K’s.

4.78 out of 5 average rating, 49 reviews

Beautiful Okemo Farmhouse 0.7 mile from base lodge

Beautiful farmhouse minutes to base lodge. Enjoy the night sky from the spacious hot tub year round. Comfortable living room with woodstove , huge family room with foozball. Eat in kitchen, dining room, 4 bedrooms, 3 bathrooms, quality furnishings throughout. Fast wifi. Gorgeous views, private 1.5 acres with barn and our own pond. Cross country skiing, hiking and sledding across the street. A gem of a house in an unbeatable location. Weekend shuttle bus to mountain in winter.

5 out of 5 average rating, 10 reviews

Home in Peru

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.

5 out of 5 average rating, 110 reviews

Stunning Views of Okemo - 3 Bedrooms, 3 Bath Home

Recently constructed on ten private acres with captivating views of Okemo resort. Three bedroom, three full bath modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or a glass of wine on the deck. Finished lower level with expansive views of the ski trails has 60" TV, games and comfy seating.