Compare vacation rentals in Wilmington, VT from 100+ sites!

This six-bedroom Wilmington, Vermont rental is located in Chimney Hill, a mile from downtown Wilmington and nine miles from Mount Snow resort.
The 6-bedroom home, sleeping 14 guests comfortably, boasts a fenced backyard, access to Chimney Hill Club Association amenities (including pools, a fitness center, and sports courts), and a well-equipped kitchen; nearby attractions include Green Mountain National Forest hiking trails.

Log Ski Lodge is a Wilmington, Vermont dwelling located approximately 23 miles from Stratton Mountain and 22-26 miles from Bennington's historical sites.
This 1080-square-foot Vermont vacation home features one bedroom, two bathrooms, and accommodates up to 11 guests, boasting a heated pool, Jacuzzi, fitness center, tennis court, and proximity to skiing and cycling trails.

Mountain Retreat is located in Wilmington, just 7.5 miles from Molly Stark State Park and Harriman Reservoir, providing easy access to outdoor activities and a peaceful escape from the city. This vacation rental has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The house offers 1400 square feet of space, comfortably accommodating up to 6 guests. Amenities include a fully equipped kitchen, a private tennis court, a swimming pool, a jacuzzi, a terrace, a garden, and a fitness center, making it perfect for families and groups looking for a relaxing and active getaway.

This Wilmington, Vermont mountain home sits on 12 secluded acres, 10 minutes from Mount Snow and 30 minutes from Stratton Mountain resorts, offering stunning views of Mount Snow and Haystack Mountain.
The three-bedroom, two-bathroom chalet sleeps eight guests and features a fully equipped kitchen, Jacuzzi, game room with pool table and ping pong, multiple fireplaces, three decks, and a hot tub, perfect for enjoying nearby outdoor activities like snowmobiling, hiking, and fishing at Harriman Reservoir and Lake Raponda.

This 3-bedroom, 2-bathroom condo in Wilmington, VT, offers a secluded escape on a private road, just a 12-minute drive from Mount Snow ski resort, a 4-minute drive from Lake Raponda, and an 8-minute drive from downtown Wilmington.
This family-friendly property, accommodating up to 7 guests, features a full kitchen with a fridge, freezer, microwave, and dishwasher, direct access to the 100 F2 snowmobile trail, and is within walking distance of hiking trails, making it ideal for outdoor enthusiasts year-round.

This charming Vermont farmhouse is located just minutes from the Mount Snow ski area and Stratton, offering easy access to outdoor activities in the heart of the Green Mountains. The property boasts excellent user, location, and cleanliness ratings, making it a popular choice for travelers seeking a comfortable and convenient stay. This spacious home has 2 bedrooms and 1 bathroom, comfortably accommodating up to 5 guests. It offers a fully equipped kitchen, a private entrance, access to a swimming pool, a garden, parking, and a 100-acre property with opportunities for hiking, snowshoeing, cross-country skiing, bonfires, and BBQ grilling.

This three-bedroom Wilmington, Vermont apartment is located in the Chimney Hill 4 Season Resort community, a short drive from downtown Wilmington, Mount Snow, and the Hermitage Club.
This 1630-square-foot rental boasts an open-concept main level, sleeps eight guests, and offers access to resort amenities including indoor/outdoor pools, a fitness center, and direct access to hiking and snowmobiling trails, plus a private she-shed and EV charging.

This Wilmington chalet is located less than 8 miles from Mount Snow Resort, about 5.4 miles from Molly Stark State Park and 10 miles from the Mount Snow Resort.
This 2,000 square foot chalet features four bedrooms, three bathrooms, a fully equipped kitchen, a hot tub, a swimming pool, a fitness center, a tennis court, and a garden, perfect for families or groups looking for a relaxing and active vacation.

This cozy A-frame home is located just 8 miles from Mt Snow, a popular ski resort, and offers easy access to other attractions like Bennington Battle Monument and Bennington Museum. The property has received excellent ratings for its location, cleanliness, and overall experience.
The 1950 square foot cabin features two bedrooms and three bathrooms, comfortably accommodating multiple guests. The home offers a fully equipped kitchen, a pool table, a terrace, a garden, free Wi-Fi, and air conditioning.

This 2,500-square-foot Wilmington house, located near Lake Whitingham and Mount Snow, offers easy access (5–15 minutes) to downtown Wilmington and Chimney Hill's hiking trails and playgrounds.
The three-bedroom, two-bathroom home features a finished basement with laundry, a wood-burning stove, a three-season room with a deck, smart TVs, and accommodates up to eight guests, potentially including a small hypoallergenic dog.

This Wilmington vacation rental is conveniently located just 0.2 miles from The Hermitage Golf Club and within easy reach of other attractions like Jim McGrath Gallery and Studio and Pettee Memorial Library. The property has received excellent ratings for location, cleanliness, and overall user experience.
The house offers 4 bedrooms and can comfortably accommodate up to 8 guests. Enjoy modern amenities like a fully equipped kitchen, a fireplace, a patio, barbecue grills, and a smoke-free environment for a relaxing and enjoyable stay.

This Wilmington, Vermont chalet is conveniently located five minutes from downtown Wilmington, twelve minutes from Carinthia, and fifteen minutes from the main lodge, offering easy access to VAST snowmobile trails.
This four-bedroom, two-bathroom vacation home sleeps eight guests and boasts a game room with ping pong, shuffleboard, foosball, and darts, plus six Smart TVs, a gas fireplace, and access to Chimney Hill's amenities including an ice rink, pickleball courts, and an indoor/outdoor pool (summer only).