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House holiday rentals in Chesterfield

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Top-rated house rentals in Chesterfield

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Top Guest favourite
A two-story black house is framed by vibrant autumn foliage. The upper deck features a green umbrella over a dining set, while steps lead down to the ground level. A hammock hangs between posts, suggesting a welcoming outdoor space.
Home in Wilmington
4.98 out of 5 average rating, 257 reviews

Cozy Mountain House- 50 acres/Trails/Whiteface mnt

Private pet friendly house, w/ 2 bedrooms, 1 bath, full kitchen and 2 living rooms. Down stairs living room is a private space w/ queen sofa bed and cozy fireplace. Located on 50+ acres in the heart of the ADK mountains, 6 mins from Whiteface Ski Resort and 20 min from Lake Placid. Hiking, mnt biking and cross-country ski trails out your front door. Open deck w/ beautiful views, opportunity to see wildlife and amazing star gazing on clear nights. Perfect for couples, small groups and families.

Guest favourite
The exterior of a wooden house is displayed, featuring a sloping entrance with a wooden walkway leading to the main entry. Large windows provide views of the lake and surrounding greenery, while colorful flower beds enhance the peaceful setting.
Home in Port Kent
4.93 out of 5 average rating, 357 reviews

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.

Guest favourite
A cottage is seen perched on a grassy bank, overlooking a river. Tall trees frame the scene, providing a natural backdrop. The water's surface reflects the surroundings, while a hint of light is visible from the cottage window, suggesting warmth inside.
Home in Willsboro
4.97 out of 5 average rating, 116 reviews

"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!

Top Guest favourite
A queen-sized bed is positioned against a wooden wall with slanted ceilings. Large triangular windows provide views of the surrounding forest and mountains, allowing natural light to fill the space.
Home in Keene
4.97 out of 5 average rating, 215 reviews

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.

Guest favourite
A log cabin with a spacious deck, constructed from natural wood, is set against a backdrop of bare trees and mountains. The exterior features large windows and a chimney, allowing for natural light and warmth. Shadows from the trees add depth to the grassy area in front.
Home in Hancock
4.97 out of 5 average rating, 105 reviews

Secluded Log Cabin with Unrivaled Views!

Luxurious log cabin on the edge of the Green Forest National Park. The house is set in a peaceful and quiet location overlooking many miles of Vermont mountains. Ideal for families and those seeking peace and solitude. Hiking and cycling trails at doorstep. 10min drive to local town of Hancock and a further 10min drive to Rochester. Wild turkeys often seen wandering across the front lawn. Wild deer and moose are in the woods. Ruby throated humming birds come to feed at the kitchen window.

Top Guest favourite
A unique bow roof home sits nestled among trees, illuminated warmly against a backdrop of a star-filled night sky. The expansive windows reflect the twinkling stars above, creating a serene atmosphere for stargazing and relaxation.
Home in Starksboro
4.99 out of 5 average rating, 203 reviews

The Spring Hill House

Escape to a haven of natural beauty and tranquility at The Spring Hill House. Our unique bow roof home offers breathtaking views of Camel’s Hump and the majestic Green Mountains, the perfect setting for a rejuvenating getaway. Despite being removed from the hustle and bustle of city life, The Spring Hill House is still centrally located, providing easy access to some of Vermont's most popular destinations. Please note: We have a firm no kids policy due to the open loft and stairs.

Top Guest favourite
A sprawling meadow extends towards distant mountains, with a varied landscape marked by trees and fields. The sky is partially covered with clouds, offering a serene view of the natural surroundings and hints of autumn colors in the foliage.
Home in Wilmington
4.95 out of 5 average rating, 534 reviews

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.

Guest favourite
An outdoor area features a circular fire pit surrounded by decorative stones, with a grassy lawn leading to a deck overlooking the lake. Sun loungers are arranged along the railing, offering unobstructed views of the water and sky under a clear autumn day.
Home in Plattsburgh
4.87 out of 5 average rating, 289 reviews

Lake Front Home in Plattsburgh - 4BR Sleeps 11!

Escape to our Lake Champlain haven! Unwind on your private rocky beach, soak in stunning lake and mountain views, and relax in our spacious, sun-filled home. Perfect for family and friends, our prime location offers easy access to local gems. Enjoy nearby City beach and Point au Roche beach. Just 10 minutes from Champlain Centre Mall for shopping. Experience lakeside living with modern comforts. Book now for an unforgettable getaway on Lake Champlain's shores!

Superhost
A spacious living area is depicted, featuring a burgundy couch and a matching armchair with nature-inspired patterns. A large area rug covers the wooden floor, while soft light filters through sheer curtains. A mirror reflects the warm ambiance, enhancing the cozy setting.
Home in Jay
4.82 out of 5 average rating, 114 reviews

Mountain Valley Retreat

This newly renovated home offers a comfortable home away from home. Enjoy an Adirondack experience at this centrally-located retreat just 10 minutes from White Mountain Ski area, 20 minutes from Lake Placid, and 15 minutes to Keene Valley. Conveniently located near many hiking, biking and cross-country ski trails. Enjoy the gazebo with new hot tub, and fire pit surrounded by Adirondack chairs. Come stay and enjoy all the Adirondacks has to offer.

Top Guest favourite
The single-story home features a modern wooden exterior with large windows that allow natural light to enter. A spacious deck is equipped with outdoor seating and leads to a grassy area surrounded by trees. The inviting structure presents a blend of warmth and contemporary design.
Home in Starksboro
4.99 out of 5 average rating, 154 reviews

Forest Hideaway

Our single story 2 bedroom 1 bath home is located within 30 minutes of Mad River Glen and Sugarbush ski areas and the quaint towns of Bristol, Richmond and Waitsfield. Drive another 15 minutes to Burlington or the Bolton Valley Ski Area. Hiking, biking and cross country skiing trails nearby, or just sit on the porch and enjoy the sounds of the nearby river. Snow tires and front wheel or 4 wheel drive vehicles necessary during the winter months.

Top Guest favourite
An open floor plan kitchen and dining area is presented, featuring a large wooden dining table surrounded by several chairs with soft textures. The kitchen is equipped with modern appliances and a spacious countertop. Natural light floods the area through large windows, accentuating the warm wood floors.
Home in Charlotte
4.96 out of 5 average rating, 100 reviews

Gorgeous Renovated Barn 20 minutes from Burlington

Historic renovated barn 20 minutes from Burlington, next to best cycling routes of Vermont, lake Champlain, beaches, hiking trails, orchards, wineries and farm to table restaurants. 30 to 60 minutes from Bolton (30min), Sugarbush (50min) and Stowe (60min). Ideal for a family of 4 or 5, or two couples. A 5 minute walk from a country store and deli and a 5 minute drive from the Essex, New York ferry. Beautiful indoor and outdoor fireplace.

Top Guest favourite
Home in Hinesburg
4.96 out of 5 average rating, 163 reviews

Sauna, Dock & 180° Views – Lakefront Retreat

Tucked on a private peninsula with 180°+ of lakefront views, our 3-bedroom retreat invites you to relax, recharge, and reconnect. Paddle from your private dock, sweat in the lakeside sauna, or sip coffee on the deck as the sun rises over Lake Iroquois. Thoughtfully designed with cozy nooks, modern comforts, and optional healing experiences, this is Vermont soul-care at its finest—just 25 minutes from Burlington.

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