Chimney Hill holiday lettings

We found 49 holiday rentals — enter your dates for availability

Why visit Chimney Hill

  • Outdoor adventures: Enjoy skiing at nearby resorts and explore scenic hiking trails in the beautiful Vermont landscape.
  • Stunning scenery: Take in the breathtaking views of southern Vermont, perfect for relaxation and exploration.
  • Family-friendly experiences: Engage in a variety of activities suitable for all ages, ensuring fun for the entire family.
  • Charming local shops: Discover quaint shops and eateries that showcase the unique character of the region.
  • Comfortable accommodations: Choose from a range of private vacation homes, stylish condos, and cosy cabins for a perfect stay.

Popular types of accommodation around Chimney Hill

If you're considering a getaway in Chimney Hill, you're in for a treat. Our most sought-after types of accommodation include houses, stylish condos, and charming cabins. Whether you're looking for a cosy house rental or an entire home in Wilmington, we have the perfect rental homes to suit your needs. Enjoy transparency, savings, and reassurance as you plan your ideal escape in this beautiful destination.

  • Houses: The top choice for visitors to Chimney Hill, offering spacious and comfortable accommodation for families and groups.
  • Condos: A great option for those seeking modern amenities and convenience, perfect for couples or small families.
  • Cabins: Ideal for nature enthusiasts, these provide a rustic and charming escape amidst the beautiful landscapes.
  • Apartments: A practical choice for those wanting a self-catering experience in a homely setting.
  • Cottages: Quaint and delightful, these offer a warm and inviting atmosphere for a peaceful stay.**

Top attractions near Chimney Hill

Chimney Hill in Wilmington, Vermont, offers a delightful blend of outdoor adventures and cultural experiences. Visitors can enjoy skiing at nearby resorts, explore national parks and nature reserves, and take in the stunning landscapes. For those needing directions, Chimney Hill Road is easily accessible, making it convenient to visit the scenic grounds of Chimney Hill. This area promises an unforgettable getaway for adventure enthusiasts and nature lovers alike.

  • Stratton Mountain Resort: Nestled 8.7km from Chimney Hill, this premier ski resort offers exhilarating winter sports and year-round outdoor adventures, surrounded by stunning mountain vistas.
  • Lake Raponda: Located 3.1km away, this picturesque lake is perfect for a romantic day out, featuring a serene beach and breathtaking scenery ideal for relaxation and outdoor activities.
  • Jim McGrath Gallery and Studio: Just 1.2km from Chimney Hill, this charming gallery showcases local art and culture, providing an enriching experience for art enthusiasts.

Things to do recommended for couples

For a romantic getaway near Chimney Hill, indulge in skiing at Mount Snow, just 3.1km away, or take an adventurous ride on the Sunbrook Ski Lift, located 2.5km away. Don’t miss a visit to Honora Winery, 5.0km away, for a delightful wine tasting experience.

Things to do recommended for families

Families will have a delightful time at Brattleboro Bowl, an arcadeAdventureZone located 11.2km from Chimney Hill, offering fun and excitement. Additionally, the Trail Head Picnic Area, situated 8.1km away, provides a serene spot for wellness and relaxation amidst nature.

Things to do recommended for groups

Enjoy a round of golf at Mount Snow Golf Course, only 2.5km from Chimney Hill. Explore the Hemmings Motor News Car Lover's Convenience Store, 9.3km away, or savour local produce at the Brattleboro Farmers' Market, situated 9.9km from your stay.

Booking with Vrbo is a breeze

Are you hoping to cut costs on your upcoming journey? Being flexible with your travel dates can be a great way to take advantage of fluctuating prices. Additionally, opting for an extended stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, feel free to use our filters to sort by price, location, and type of holiday rental.

Where to stay near Chimney Hill

Chimney Hill, nestled in Wilmington, Vermont, offers a delightful blend of family-friendly experiences and stunning scenery. Explore the charming southern Vermont region, where adventure awaits in the form of outdoor excursions and romantic getaways. Enjoy the recreational areas that showcase the beautiful Vermont landscape, perfect for those seeking both relaxation and adventure. Whether you fancy hiking trails or quaint local shops, you'll find plenty to enchant you in and around Chimney Hill.

  • Wilmington: Wilmington is a charming town located 1.9km from Chimney Hill, renowned for its outdoor adventures and sporting activities. Set against a backdrop of picturesque mountains and valleys, it is a haven for skiing enthusiasts with numerous ski resorts and fields nearby. Visitors can indulge in a variety of winter sports, while the surrounding natural beauty makes it an ideal spot for hiking and exploration during warmer months. The local lakes provide opportunities for fishing and leisurely days by the water, ensuring a memorable experience for all who visit.
  • West Dover: Situated 2.5km from Chimney Hill, West Dover offers a delightful blend of adventure and relaxation. This quaint town is a popular destination for skiing, with several ski resorts and fields catering to both beginners and seasoned skiers. The stunning landscape of mountains and valleys enhances the outdoor experience, making it a perfect location for hiking and exploring nature trails. In West Dover, visitors can enjoy the serene beauty of the local lakes, ideal for picnicking or simply soaking in the tranquil surroundings.
  • Bennington: Located 9.9km from Chimney Hill, Bennington is a vibrant city known for its rich history and outdoor recreation. Skiing remains a highlight for adventurers, with easy access to ski resorts and fields. The area is also home to historic landmarks, including a renowned college, adding a cultural aspect to your visit. Surrounded by beautiful mountains and serene lakes, Bennington offers a perfect setting for both exhilarating activities and peaceful retreats. Whether you're exploring the local history or enjoying the great outdoors, Bennington has something for everyone.

Best time to go to Chimney Hill

If you're planning a trip to Chimney Hill, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in February and July to August, while off-peak times, like April to May and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January20.3°F (-6.5°C)Light RainMostly CloudyAverageSlightly High
February22.3°F (-5.4°C)Light RainMostly CloudyModerately HighSlightly High
March30.0°F (-1.1°C)Light RainMostly CloudyAverageAverage
April41.9°F (5.5°C)Light RainMostly CloudyModerately LowSlightly Low
May54.5°F (12.5°C)Light RainMostly SunnyModerately LowAverage
June62.1°F (16.7°C)Light RainMostly SunnyAverageAverage
July68.2°F (20.1°C)Light RainMostly SunnyModerately HighAverage
August66.0°F (18.9°C)Light RainMostly SunnyModerately HighAverage
September59.2°F (15.1°C)Light RainMostly SunnyAverageSlightly Low
October48.0°F (8.9°C)Light RainMostly CloudyAverageSlightly Low
November35.8°F (2.1°C)Light RainMostly SunnyModerately LowAverage
December27.1°F (-2.7°C)Light RainMostly CloudyAverageSlightly High

What do I need to keep in mind when booking a vacation around Chimney Hill

When you’re planning a trip—whether with friends, family, pets, or for an extended stay—be sure to use the appropriate filters to align with your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Chimney Hill with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options, and more, on Vrbo.
  • Traveling to Chimney Hill with young kids: Traveling with young children can present its challenges. It's essential to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are suitable for families.
  • Taking your pets with you to Chimney Hill: For many, a family holiday isn't truly fulfilling unless their furry companion is along for the adventure. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Chimney Hill: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly accommodations. Don’t forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Vrbo Trips: Planning as easy as it gets

Vrbo's clever Trip Board offers you a dedicated space to plan your next adventures, pick up from where you last paused, or manage your travel arrangements with ease. You can easily access the properties you've previously saved and booked, now organised under Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

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