Kid-friendly holiday rentals in Windsor County

1st floor, Okemo contemporary country 3 BR 2 BA

Family-friendly, pet-friendly, clean, comfortable, contemporary country ski cabin on Okema shuttle buss route in Ludlow, VT, a few minutes from mountain. Very easy access to outdoor activities: skiing, hiking, lakes, boating, hunting, snowmobiling, fly-fishing. Updated, comfortable, light filled ambiance. Great location, 10 minute walk to downtown (2 minute drive). Great for groups, couples, families. Recently renovated. New butcher block counter-tops and island, all new kitchen, new bathrooms.

Gigi and Pops' Secret Cabin

Newly built cozy vacation home perfect for 3 generation adventure. We built this home to entertain and build memories with our grandchildren and we hope other families do the same. Very close to Pico and Killington ski resorts and lots of beautiful Vermont attractions. 5 miles (9 min drive) from Mountain Top Inn and Resort.Besides sleeping 10, we made sure 10 can sit at the large island and also sit together in living room. We love our basement playroom and treehouse as much as our grandkid do!

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.

NEW Killington Studio: Great Location! Comfy. 431

Welcome to our Killington studio, perfect for skiing, biking, hiking, antiquing, beer tasting, kayaking, exploring, or simply unwinding. This hotel room-style condo sleeps four in two comfortable queen beds. Enjoy cable/streaming on the large smart TV. Amenities include a mini-fridge, microwave, Keurig & coffee maker. The full bathroom offers a tub & shower. Outside, a heated pool awaits (open June to mid-September). You'll love it! (Note: This unit is hotel-room style without a kitchen.)

Luxury Modern Cabin near Okemo & Killington

All-seasons fun for the whole family in this brand-new home with unparalleled privacy! Modern design elements, tranquil scenery, and 21st century comforts set the backdrop for the perfect getaway. Enjoy ski season in this mountainside abode that's 10 minutes from Okemo, 20 minutes from Killington, and close to downtown Ludlow & Camp Plymouth State Park. Golfer-friendly in spring, summer, and fall. In all seasons, enjoy hiking, leaf peeping, brewery hopping, and swimming.

Modern Dog-Friendly/Fireplace/Spa/Pool/Tennis/AC

This beautifully renovated, dog-friendly 2-BD, 2-BA home in The Woods combines comfort and modern style. It boasts a spacious living area with a cozy wood-burning fireplace, a fully equipped kitchen, and entertainment options like an arcade game system and Xbox S. Just steps away, enjoy premium amenities including an indoor pool, hot tub, and spa. Plus, the Killington Café and Wine Bar next door offers the perfect spot to relax and unwind—an ideal retreat for any getaway!

Peaceful Vermont Mountain Cottage -Pet Friendly!

Unwind and create lasting memories with family and friends at this peaceful country retreat. Nestled on a quiet acre just 15 minutes from town, it's the perfect escape from the everyday hustle. This spacious home features 4 bedrooms, 3 bathrooms, a cozy fireplace, and a backyard fire pit—ideal for chilly nights under the stars. Explore charming local towns, discover hidden gems, and enjoy the best of Vermont living.

3BR 1Bth New England Cape - Experience Vermont!

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!

"Downtown" Norwich Apartment

You get the best of both worlds with this kid friendly and modern 2br apartment inside the oldest house in Norwich - conveniently located 1 mile from Dartmouth Green and a five minute walk from Dan & Whit's. There are two small bedrooms (1 with a queen bed, 1 with a twin over full bunk bed and a single sleeper sofa), bath with laundry and tub, washer and dryer, and full kitchen.