House holiday rentals in Chesterfield

Aunt Shy's Hide-Away

Aunt Shy's hide-away is nestled on a dead end road in the Spruce Mill Brook Valley bounded by Saddle Hill and Hood Mountain (both on the 250-acre property). Situated in the Adirondack Park midway between the High Peaks and Lake Champlain (Exit 32 on I-87), this property is in an ideal base for enjoying the Adirondack Mountains and Lake Champlain Valley. Looking to get away from the daily grind, hike, bike, fish, ski, or just relax by the fire. Five minutes to the Meadowmount School of Music.

18 Lake Stunning View of Champlain in Adirondacks

Welcome to 18 Lake. Situated in beautiful, quiet, Port Kent, NY, this gem is the perfect place to relax and get away. People come from all across the country to tour this charming area on bicycles in summer, and from all over the world during the winter for Lake Placid's winter sports. In fall, the colors are vibrant and breathtaking. Fresh maple products are on tap in Spring. Enjoy area attractions such as Ausable Chasm, High Falls Gorge, Port Kent Beach, golf, orchards, hiking and biking.

The Cabin at Pinestone - Adirondacks/Whiteface

Construction was just completed on this small, 2 bedroom cabin located in the heart of the Adirondacks. Everything in this house is brand new. Minutes from every attraction; Whiteface Mountain, Lake Placid, Mountain Biking, hiking, etc.. Quiet, private location would make for a perfect romantic get-away or comfortable place to relax after a busy day. Modern amenities include: Rustic furnishings, shiplap, barn board, granite countertops, heated bathroom floor, dishwasher, central air & fire pit.

"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!

Modern, hilltop, lakeside retreat!

A minimal, refined retreat nestled in trees offers peaceful, modern luxury. Use the dock for swimming and relaxing, kayaking, and paddleboarding. Built in 2021 to the highest standards, for extended family. Located about 15 minutes from downtown Burlington & downtown Winooski w/ access to all manner of outdoor & maritime activities! We encourage you to enjoy coffee on the dock in the morning! Views from the house vary with the season due to the leaves on the trees. The lake is always beautiful.

Quiet 3 Bedroom Cottage on Lake Champlain

You'll have a relaxing visit at this cozy, comfortable family camp. Enjoy swimming, kayaking and hiking. Explore gorgeous Lake Champlain or enjoy the view from the porch. The sunrises are spectacular! Lake Champlain is known for great year-round fishing. Tip: Bring your water shoes for maximum swimming comfort. Hop on the Essex Ferry to Vermont to experience shopping, art, restaurants and museums. The Shelburne Museum and ECHO, Leahy Center for Lake Champlain are perfect for families.

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 VIEW! THE VIEW! THE VIEW!

A 1900 farmhouse that has been in the family for generations. Recently renovated to accommodate up to 5 guests, it is clean with simple furnishings and a SPECTACULAR VIEW! Located RIGHT ON NYS RTE 86 (close to the road) with easy access to nearby attractions. The house is split in 2 and is designed for 2 families. I rent out "The View" using airbnb exclusively. My wife and I reside in the back portion of the house with a separate entrance and separate parking.

Ultimate Whiteface Race Base: Hot Tub & Views!

Gear up for the 23rd Whiteface Mountain Uphill Bike Race on June 6, 2026! Stay at Sugar House ADK Base Camp, the perfect retreat for tackling the 8-mile, 3,500ft climb. Just 23 min from Lake Placid, enjoy majestic views with Fido, hiking trails, and a hot tub for recovery. Relax fireside with hot cocoa or challenge friends to ping pong and billiards in our farmhouse with a full kitchen/coffee bar. Make unforgettable memories at the ultimate race base!

Birchwood Lodge - Our Home in the Woods

Birchwood Lodge is only four miles from the entrance to Whiteface Mountain. The property in Wilmington is nestled on three wooded acres with a babbling stream that meanders past the screened-in porch on the back of the house. This is a great place to create vacation memories as you explore the Adirondack and Olympic offerings or join the young at heart and explore the woods and stream in your own backyard at Birchwood Lodge.

Secluded Chalet w/ Hottub & Stunning Mtn Views

Welcome to our cozy secluded Jay Peaks Chalet! Tucked away on 11 acres of natural beauty, this charming home is just a 15-minute drive from White Face Mountain, making it the ideal starting point for your mountain adventures or relaxation. Cozy bedrooms with forest views, a private hot tub, Firepit, screened in porch, and plenty of privacy. Book now for an unforgettable escape for the entire family. Your dogs will love it too!

WTR; 6 ppl, 0-2 top dogs, bike, hike, fish, relax!

Wilmington Terrace Ranch is a welcoming 3 bedroom / 2 bath home with outdoor space in 'downtown' Wilmington. Whiteface, restaurants, convenience store / gas, fishing, hiking, cycling / mountain biking all close (walk to store, beach). The home is on the market, so occasional daytime showings may be requested with 24+ hours notice. We coordinate to minimize any disruption and will always respect your schedule.