Condo vacation rentals in Cavendish

The living area features high wooden beam ceilings and exposed brick walls, creating a rustic ambiance. A cozy wood burning fireplace is situated beneath the wall-mounted television. Comfortable seating includes a checkered sofa and a leather chair, all complemented by a central area rug.

4.96 out of 5 average rating, 151 reviews

Cozy Ski Condo In Historic Mill - on shuttle route

2 bedroom, 1 bathroom condo located in the historic Mill Building (1834). This top floor end unit offers views of Okemo Mtn while overlooking the Black River. With exposed brick walls, wooden beams, high ceilings & a wood burning fireplace we hope you enjoy the coziness of this rustic space after a long day of adventure. Firewood, linens, towels, & cooking needs are provided for added comfort. Our condo is centrally located, walkable to shops/restaurants & is on the shuttle route to Okemo.

4.94 out of 5 average rating, 17 reviews

A comfortable living area is highlighted by a cozy leather sofa and a rustic coffee table on a soft area rug. A flat-screen television is mounted above a gas fireplace, while large glass doors lead to an outdoor patio, allowing natural light to fill the space.

Condo in Cavendish

Castle Retreat Pool Spa and Mountain Adventures

Escape to this stylish 3BR condo at The Castle Resort & Spa—your home base for mountain adventure and total relaxation. Swim in the year-round pool, unwind at the spa, and explore nearby lakes, waterfalls, and hiking trails. With space for 8, a full kitchen, AC, and beautiful views, it’s perfect for families or friends. Just 10 minutes from Ludlow and Okemo, this retreat offers comfort, convenience, and a perfect way to experience Vermont in every season—summer and beyond.

4.99 out of 5 average rating, 181 reviews

A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.

Condo in Killington

Alpine Condo - AC & Pool - Golf & Bike

Updated 1-bedroom Whiffletree condo with stylish alpine feel—steps from Killington Resort, golf course, and access road. Thoughtfully stocked with essentials, plus a private gear locker for convenience. Relax at the onsite outdoor pool (open Memorial Day–Labor Day). Sleeps 4 with a king bed and queen pullout sofa. Portable AC unit in the living room helps keep the condo comfortable Pack & Play crib, mattress and sheets available upon request. Reg #007718

A cozy living room features warm wooden paneling and a plush sofa facing a mounted flat-screen television. A circular coffee table sits in the center, complemented by a floor lamp and a side chair. A fireplace adds a comforting touch, creating a welcoming space.

4.95 out of 5 average rating, 193 reviews

Lovely 1-Bedroom condo with indoor fireplace!

This cozy condo is exactly what a close group of 4-5 people need for a wonderful ski experience. Located centrally in the beautiful town of Ludlow this location is close to everything you could want. It sits on the bus route for Okemo Mountain, and is walkable to groceries, restaurants and bars. "Eight Oh Brew" tap house is located on the base floor of the building. This location has free onsite parking, free firewood and coin laundry machines.

The living area features a cozy fireplace surrounded by stone, with a wooden mantel. A dining table with white chairs is positioned near the kitchen, complemented by bar stools at the counter. Light floods in through large windows, enhancing the open layout.

4.96 out of 5 average rating, 116 reviews

Winterplace - Steps away from Slopes

Newly updated condo at Winterplace Okemo. This sunny corner 3 bedroom unit is just steps to the top of the A-B Quad. Completely renovated from floors to ceiling The delightful fireplace place will keep you toasty in the cozy living area. Outdoor ski locker just outside back door. Front door parking, and firewood included. Pool is open and available to renters all year. Hot tub in winter months and tennis courts in summer.

A view of the snow-covered path leading to the ski slopes is framed by the C Building’s balconies. Sunlight casts long shadows across the pristine snow, highlighting the tranquil winter scene. The surrounding area is clear and inviting, with ski signage visible in the distance.

4.93 out of 5 average rating, 175 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Please note there is no AC at this condo complex summer time

4.97 out of 5 average rating, 153 reviews

A living area is presented with a spacious purple sectional sofa and an accent chair, creating a comfortable seating arrangement. A wooden coffee table occupies the central space, and large windows allow natural light to fill the room, revealing a snow-covered landscape outside.

Condo in Eastman

Cozy Light-filled Condo in Charming Eastman

Light, bright and cozy three level condo with cathedral ceilings, two bedrooms, and a family room in the lower level with multiple sleeping arrangements. The lower level walk out makes a two minute walk to a beautiful beachfront on Eastman Pond. Close to Sunapee Mountain Ski Resort, and cross-country and snow shoe trails too numerous to list! Easy access to Rt 10 and I-89 for convenient commuting.

4.95 out of 5 average rating, 178 reviews

Condo in Killington

Ski-In/Out, AC, Pools, Hot Tub, Pet-Friendly

Escape to a spacious, pet-friendly 1-bedroom mountain condo in Killington, comfortably sleeping 4. Enjoy year-round adventures with easy access to hiking, biking, golf, and skiing. The condo is 488 ft to the sunrise lift! Relax on your private balcony, by the gas fireplace, or at the resort's indoor/outdoor pools, hot tub, and fitness center. Perfect for a serene mountain getaway with all amenities.

4.89 out of 5 average rating, 37 reviews

A cozy bedroom features a spacious bed adorned with a quilt. A large window allows natural light to filter through, complemented by soft curtains. There's a wooden dresser and a bedside table with a lamp, while a chair provides additional seating.

Condo in Cavendish

Condo at Castle Hill

This beautiful one bedroom, condo is located at the peaceful and scenic Condos at Castle Hill. Four miles to Okemo Mountain and Fox Run golf course and one mile to restaurants of Proctorsville, and 2 miles to Ludlow. This is the perfect setup for your ideal mountain getaway. One full bedroom, full bath with a pullout couch in the living room, sleeps four. Don't miss out on this Okemo getaway!

Superhost

A spacious living area is showcased, featuring comfortable leather sofas and a decorative wall clock. A television is positioned near a fireplace, complemented by a stone hearth. Natural light filters through two windows adorned with light fabric curtains, highlighting the wooden beams of the ceiling.

4.75 out of 5 average rating, 99 reviews

3-Bedroom Condo in the heart of the Village @Okemo

Your family will be close to everything when you stay at this centrally-located main floor condo located at The Mill. Two queen bedrooms and a quad bunk room with TV for the kids to have their own space and enjoy. Okemo is approximately 1 mile up the road and Killington is a 30 minute drive. The area also offers great hiking, mountain biking, lakes and swimming holes for year round fun!

4.96 out of 5 average rating, 217 reviews

Condo in Killington

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

Revel in this bright and modern ski condo just off Killington's main road and close to everything. Relax after a day on the mountain streaming on one of your 3 smart TVs. Indulge with the fabulous condo amenities including the pool, hot tubs, spa, gym, and tennis courts, or settle in by the wood-burning fire. Spread out in this spacious condo and enjoy all that Killington has to offer.

A view of an open-concept suite showcases a kitchen countertop with a sink and decorative flowers. A cozy living area is visible, featuring a red sofa and a dining table. The master bedroom is visible in the background, fitted with a king bed and soft lighting.