Pet-friendly holiday rentals in Chesterfield

Adirondack Timberwolf Cabin

Cozy Mountain Chalet in Jay, NY on beautiful Glen Road. Only .7 miles to the Jay Covered Bridge, 3 miles to the Jay Mountain summit trail head, 7 miles to Whiteface Mountain, and 16 miles to Lake Placid. Keene and Keene Valley trail heads are only minutes away. The cabin has 3 acres of wooded property with a front driveway as well as a back access drivweway which is nice to walk. There is strong Wifi World Class Fishing, Ausable Rivers are close This is our family cabin. Enjoy it as we have.

"Beau Overlook" Enjoy 2 states from 1 great spot!

Come enjoy LOGISTICS to the Green Mountains of VT & the heart of the DACKS in one sweet spot. "Beau Overlook Cottage" perched high on the banks of the BOQUET RIVER, with sweet sounds of water tumbling over river rocks below. This home is situated 2 miles north of the Lake Champlain ~ Boquet River Delta. The beautiful LAKE scene at the sandbar of the delta must be seen to be appreciated. This relaxing sanctuary will provide an upscale and sophisticated home, whose logistics cannot be beat!

The Brookside Cabin

Our Cabin is nestled in the woods of the Adirondack Mountains. The Cabin is behind our family home. We are on a country road close to two towns. Our area offers many amenities such as fishing, hiking, boating, golf, hunting , wine tasting, leaf peeping. The cabin is heated by a wood stove and is the only heat source. “Wood Stove will injure a small child. Fast moving water in brook. Children 7 and up is ok with pre approval. The outside shower is heated, hot water available mid April -Nov.

A-Frame | Hot Tub | Dog Friendly | Fenced Yard

The mountains are calling! Escape to our cozy, yet modern, Blue Hour A-Frame located in the rustic AuSable Acres neighborhood. The fenced backyard is carefree for your pups to play in while you enjoy the hot tub & fire pit. Whiteface Mountain Ski Resort is 11 miles/20 minutes away, by way of a scenic notch along the West Branch of the Ausable River. Lake Placid is 20 miles/35 minutes away. Dogs welcome at $75 per dog (no cats, please), per stay, up to two dogs. No cats due to guest allergies.

Ascent House | Keene

A unique retreat meticulously crafted for resting and recharging after exploring in our beautiful Adirondack Wilderness. Flooded with natural light, every room offers calming frames of nature. Watch the sun peak through the forest and rise over the mountains through expansive windows. Ascend the levels of the house, each revealing more landscape. Experience a designer woodfired traditional Finnish sauna & totally recharge while embracing our harsh Adirondack weather. We hope you love it here.

The Rustic Retreat at Twin Ponds

Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away. You’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. Wake up to coffee on the deck or take a stroll around the pond. And you won’t regret kicking back in the evenings - star gazing is simply magical! We are certain that you‘ll have a hard time leaving!

Adirondack Cabin Retreat – Hot Tub + Lake

Plan a peaceful stay for up to 5 people in this cozy, well-appointed cabin with lake access that marries rustic charm with modern amenities. This is a vintage Adirondack retreat with access to a quiet and private lake perfect for swimming, paddling and fishing. We have loons and a resident bald eagle. A local winery and brewery are so close by too! Ausable Chasm is fun family-friendly attraction just down the road. Lastly for security, we have a camera focused on driveway entrance.

Nine Sides Lodge- base camp for ADK Adventures

Nine Sides Lodge -3 Beds/1 Bath in the classic ski chalet, A-frame style with fresh and clean updates. -10min to Keene hiking, 15min to Whiteface Mt, 30min to Lake Placid. -Hiking, snowshoeing, XC Ski trails, stream and pond fishing - all in the neighborhood! A-frames are perfectly designed to re-kindle relationships and build a sense of togetherness! In other words, if you don't like being around your friends and family, stick to hotels. But stay here, and give your friends FOMO

The Shepherd's Crook at Blue Pepper Farm

Tucked in the woods on our working sheep farm, our off-grid tiny house is the perfect escape and stepping stone into the Adirondack mountains for hiking, skiing, and snowshoeing. Enjoy the coziness of the Crook between forays into our north country wilderness! What you will find: adventure, peace, quiet, woodstove, candles, down blanket, fire pit, privacy, composting outhouse, firewood for sale. **Please note there is NO electricity and NO running water. Akin to glamping!

The Cabin @ The Birches

Nestled on the serene shores of Lake Champlain, this rustic log cabin offers the perfect escape from city life. Located at 41 Kibbe Farm Rd. in South Hero, VT, this idyllic retreat promises tranquility and natural beauty in abundance. Whether you seek a peaceful retreat or an adventure-filled getaway, this lakeside log cabin provides the perfect setting. Book your stay today and experience the beauty of Vermont from the comfort of your own cabin on Lake Champlain.

The Trailhead

Our guest suite is located on our small horse farm in the foothills of the Adirondacks. The space has a cozy rustic charm, and has everything you’ll need for a quiet mountain getaway in any season. We are located right at the entrance of the Blueberry Hill Trails, a 1000-acre trail system designed for hiking, snowshoeing, skiing, mountain biking, and horseback riding. Head out the door and you're right on the trails.

The Paddle Inn

Our house is very open and spacious. It is designed to get around easily. There are multiple places to sit and eat or enjoy nature. The house has numerous windows and is well lit. There is a lot of deck space and a big back yard for games. We are always friendly and open, just down the road if anything is needed! We love meeting new people and do what we can to make your stay comfortable!