Townhome holiday rentals in Rutland County

The Chillington at Sunrise (ski in/out)

Welcome to our slice of heaven! No matter the season, The Chillington is a spacious 3-bedroom/2-bath retreat that has just about everything to offer. Located in Sunrise Village, you will have direct access to the trails and lifts (snow conditions permitting), as well as hiking and snowshoeing right outside your door and mountain biking nearby. The clubhouse has an indoor pool and spa, an outdoor spa and pool (heated, summer only), a fitness center, and a seasonal restaurant. You'll love it here!

Williams on Main - Love Ludow. Live VT

The spacious Williams on Main House is in the heart of Ludlow within walking distance to all restaurants and entertainment. Sleeps 10 comfortably. Only a mile from Okemo, 35 min to Killington/Stratton and 40 to Mount Snow: ski/ride, bike, hike! Enjoy the large living area with working fireplace and an enclosed & covered outdoor jacuzzi / bike / kayak storage area. Two bedrooms on the second floor (2 queens) and a finished attic (1 queen, 1 full, 1 full pullout). Two dedicated parking spaces.

Topridge 3BR w Incredible View & Private Hot Tub!

Oso Dream provides AMAZING panoramic views of Bear Mountain. Step out the front door and ski down Sundog trail to Sunrise Village Triple or step out the back door and hop onto Bear Cub trail to access Bear Mountain! Enjoy the amenities within the complex including indoor & outdoor heated pool (seasonal), sauna and gym. Guests also have access to the outdoor skating rink and xc ski trails (weather permitting). Free use of ice skates, puff hockey equipment, snow shoes, xc skies, poles and sleds!

Dog Friendly Mountain Condo w/Spa, Pool, Sauna

Escape from your suburban home and come enjoy our beautiful Killington getaway condo. Boasting a spacious, comfortably furnished interior, this modern 2-bedroom, 2-bathroom abode is perfect for families, multiple couples, or a romantic getaway. Our Killington Air BNB has far more than the average Air BNB with everything you need for a great experience. If you're working during your stay you'll find high speed wifi and a dedicated desk space. Pool and Spa area closed 5/4-5/15 for maintenance

Bear Woods Lodge

Come stay in this chalet style property on a dead end off the access road! Endless rear woods, exposed beams, plenty of parking, and easy access make it perfect for getting together with friends or family. PLUS! Desks, fast internet, and onsite laundry make remote working/long term stays a dream come true. Restaurants, Pizza, Bars, Ski/Board Shop, Ice Cream, and more are all within an easy 5-10 min WALK. Only a 5 min drive to the lifts or catch the shuttle right at the end of the road

Prime location off Killington Rd

You will be close to everything at this centrally-located townhome. THE HEIGHTS AT KILLINGTON. PRIME SPOT LOCATED OFF THE KILLINGTON ACCESS ROAD. Gorgeous luxury 3 bedroom, 3 bath townhouse with spectacular mountain views, 3 levels, & oversized garage. Open concept floorplan on the main level. High speed Internet w/Mesh Wi-Fi system. 2 King size bedrooms. TV's in every bedroom & large 75" TV in Family Room. Bonus Bunk Room has 2 twin-over-full bunks & 65" TV. Gas fireplace & Central A/C.

Retreat in Ludlow

Trestle House is the place to stay for all the skiing fun. It’s in the heart of Ludlow. A very short distance to Buttermilk Falls and, of course, Okemo Mountain for all your winter activities. Walking distance to all restaurants and entertainment. Can’t forget Dorsey park. Only a mile from Okemo, 35 min to Killington/Stratton and 40 to Mount Snow: ski/ride, bike, hike! Enjoy the large living with board games. Four bedrooms on the second floor (1 king , 1 queen , 4 singles ).

Ski-in / Ski-out 3BDR+ Killington Condo at Sunrise

Welcome to your ski-in / ski-out townhouse, where you have direct access to the Sunrise Village Triple lift during winter and year-round access to all the Sunrise amenities. With over 2,300 square feet of living space, this is a great place for family and friends of all ages to gather. Enjoy the coziness of a classic VT cabin/lodge, plus todays' comforts & amenities like the renovated kitchen, three full bathrooms + a steam shower, wood-burning fire place and fiber-optic WiFi.

Renovated 2bd/2.5bath/Den + Pool Access (pets ok)

Recently updated ski condo - modern kitchen appliances and new furniture. Minutes away from Killington Ski base. Drive there or use a paid bus service, steps away from the condo. Part of the luxurious Woods Spa Resort and stay includes use of resort amenities including gym, pool, steam/sauna and hot tub. Spa service available but not included in fee (please check for open hours) Warm, cozy and welcoming-custom built for ski lovers to relax after a long day on the mountains.

Townline Triplex

This newly refurbished country home is settled along the spine of the Green Mountains, centrally located right on scenic Route 100. This welcoming 3 unit, 6 bedroom Triplex boasts easy access to the VAST snowmobile trail system & is just a couple miles outside of the quaint town of Pittsfield where you will find local markets, restaurants & gas. Just 12 miles to Killington & 28 miles to Sugarbush, Townline Triplex offers a memorable gathering place for your whole group!

Ski on/ski off with hot tub

Ski on/ski off of idyllic mid-mountain Sachem (green trail) to this spacious 3 bed, 3 bath, hot tub townhome in Trailside Village. With an open concept main living area and a loft space, there is plenty of room to relax with family and friends after a day of skiing. In the Summer, enjoy the community pool across the street or access the lifts, mountain biking, zip-line tours, kid-friendly adventure zone, Okemo Valley Golf Club, and many hiking trails.

Topridge Style 3BR: Hot Tub, Ski On Ski Off, Views

This elegant 3BR/4BA townhouse in Sunrise Village offers breathtaking views & ski-in/ski-out access (weather permitting). Features include a cozy gas fireplace, chef’s kitchen, private 2-level deck w/ hot tub (under the stars!) & BBQ grill. Enjoy the game room w/pool table, high-speed Wi-Fi, & access to Sunrise Sports Club amenities (indoor pool, gym, & sauna). Pet-friendly, close to skiing, dining, & hiking. Book now for your perfect Killington getaway!