House rentals near Okemo Mountain Resort

Stylish Vermont Cabin | Views · Trails · Luxe

Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

Newly renovated. Minutes to Slopes & Trails

Healdville Hideaway has 3 acres of rural charm located on the backside of Okemo Mountain. Charm is a plenty in this 1500 SF single story, newly renovated home with views of the mountain & fields full of wildlife. This modern country decorated home provides the perfect comfortable setting for single or multi family enjoyment. The fully functional kitchen is available for making a quick snack or a full meal. The back acreage is perfect for building a snowman or doing a little cross country skiing.

The Bluebird Day Chalet 2 bed dtwn Ludlow Village

Cozy heart of Ludlow Village location on the shuttle route (free!) for Okemo & close to Echo Lake that sleeps 6. As downtown as possible! Okemo shuttle stop at The Mill. Quick walk to good eats & drinks (Downtown Grocery, Stemwinder, Main + Mountain, etc.), Shaws, Rite Aid, and The Wine & Cheese Shop (perfect for après ski!). On site parking for 2 cars & free on street parking if needed (no overnight). Wifi & smartTV to stream your favorites while you relax after a long day on the slopes.

Midcentury Hillside Retreat - Summer Paradise

Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.

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.

OKEMO GETAWAY Hot Tub & Fire Pit WALK TO TRAILS!

Please note: NO SATURDAY CHECKOUTS/INS during Winter season which runs November through April - any other day ok the week is OK :) Saturday check-ins during spring/summer OK with prior approval from host. 5 bedrooms, hot tub and outdoor fire pit, fireplace, loft, sleeps 14, 3 full baths, two living rooms, this Okemo Mountain home is the perfect Vermont getaway within walking distance of the slopes. Our home is nestled in the woods and is the perfect spot to relax, have fun, and enjoy life!

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned 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 unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

Ski Chalet with Hot Tub on Okemo Mountain

Newly renovated in fall 2023, this 3-level, 1700+ sq. ft. ski chalet is just a 4 min drive to Okemo Mountain Resort and town, with Jackson Gore only 6 min away. Floor-to-ceiling windows showcase stunning 180-degree views of the wooded backyard, creating a peaceful mountain retreat. Cozy up by the fireplace or soak in the Jacuzzi hot tub for ultimate relaxation. Whether you're here for skiing, hiking, or a quiet escape, this private oasis offers the perfect blend of comfort and convenience.

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Charming Vermont Schoolhouse

Kick back and relax in this calm, stylish space. A beautifully restored schoolhouse circa 1860 welcomes you. Situated on a quiet country road this adorable home on one wooded acre has lovely mountain views and a peaceful setting. Nearby you will find skiing, hiking trails and quaint Vermont towns with shops and restaurants. Manchester and Rutland are 30 min. drives, Dorset is just 20 min. Granville NY has a large grocery store and other shops and is only a 15 min. drive.

Meadow View. 35 acres outside your door!

Meadow View - pet friendly home away from home. 35 acres- including 2 trout ponds and 25 acres of wooded trails (perfect for hiking, cross country skiing/snow shoeing!). Featuring a newly remodeled kitchen and bathroom. Minutes from Mt. Ascutney (trails galore, rope tow in the winter). The unit is perfect spot for couples craving time in rural Vermont or for families/outdoor enthusiasts who want to go mountain biking, skiing, hiking. (Okemo 30 min Killington 45 min)

Renovated Vermont Schoolhouse – Close to Okemo

Time for recess! Our totally renovated and expanded schoolhouse is a perfect retreat with all the comforts of home. It has high ceilings, lots of natural light, and plenty of spaces to gather or have some quiet time. Fully stocked kitchen w/DW. 3 bdrms (3 beds, 2 queen/1 full), 2.5 baths. W/D. Close to Ludlow, Okemo/Jackson Gore, Stratton, Killington, Castle Hill Spa and plenty of lakes and ponds.