Holiday rentals in Westport

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Top-rated holiday rentals in Westport

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Top guest favourite
An outdoor porch is featured, with a simple wooden table and benches positioned under a slanted roof. Flower pots add color near the railing, and a plush rug lies beneath the table. Lush greenery surrounds the area, providing a serene natural setting.
Home in Westport
4.99 out of 5 average rating, 113 reviews

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.

Top guest favourite
An outdoor seating area is visible, featuring two white Adirondack chairs positioned beside a fire pit. Stones surround the flames, which are softly glowing. A gravel path leads to a rustic barn with an orange door, surrounded by trees and outdoor string lights.
Barn in Monkton
4.99 out of 5 average rating, 567 reviews

Cozy VT Barn by Burlington-Firepit-BringUrDog-WiFi

Cozy barn, gas fireplace, fast WiFI in a peaceful wooded forest. Whether sipping coffee by the fire, spinning vinyl records or stargazing by the fire pit(wood provided), this is your space to disconnect or work remotely in comfort. Explore on-site hiking trails, snowshoe and spot wildlife. A short drive from breweries, restaurants, scenic hikes & towns. A perfect mix of seclusion & convenience, 35 mins to Burlington. Perfect for couples/solo travelers/anyone looking for a private nature escape.

Top guest favourite
A spacious deck extends from the cottage, furnished with seating and a dining table. Colorful planters and artwork decorate the area. Large windows reflect the surrounding trees, while a yellow and blue umbrella offers shade. Relaxing lounge chairs are positioned on the lawn, inviting guests to unwind.
Cottage in Panton
4.97 out of 5 average rating, 262 reviews

Panton / Near Vergennes , Middlebury Private Home

Begin your Vermont experience at our serenely secluded, wooded hide–a-way. This inviting private home features all the best amenities including luxury linens, fully equipped kitchen, bath with custom over sized shower, a beautiful deck with gas grill, teak and glass dining table, and lounge seating for 4. It is the perfect space for 2 adults and children, or up to 4 adults, providing easy access to the best Vermont has to offer from Lake Champlain, Vergennes, Middlebury, and all points beyond.

Guest favourite
A charming cob house is nestled amid trees and snow-covered ground. Natural elements, such as logs and stones, adorn the exterior, while a sloping roof showcases wooden beams and a window. A rustic door invites guests into this unique and cozy retreat.
Earthen home in Essex
4.93 out of 5 average rating, 118 reviews

The Cob House: private & unique Adirondack cottage

Handmade cob house lovingly created by us from sand, straw, clay & other found objects. Perfectly unique "glamping" getaway nestled on the edge of the woods & a quiet stream. Close to many Champlain Valley attractions in Essex, NY in Adirondack Park (10 min. from VT ferry, 30 min. from High Peaks). Rustic, private retreat complete with outhouse, cook shelter, wood stove, fire pit, and on outdoor heated shower. Unplug & enjoy! (no Wifi, limited cell service).Cozy launching point for adventure!

Top guest favourite
A scenic view of a lakeshore property is captured, featuring a beautifully landscaped garden and a house set against a backdrop of trees. The calm water reflects the greenery, while a stone wall separates the yard from the beach area.
Flat in Vergennes
4.99 out of 5 average rating, 311 reviews

Lake Champlain charming apartment amazing views

Charming, bright apartment attached to a 2007 custom Vermont country french home located on the shores of Lake Champlain. Breath taking westerly Adirondack views offer dramatic sunsets and lake views of Button Bay. The property consists of 12 acres of fields, woods, stone walls and gardens with the home situated privately looking over the lake shore. The apartment has a private entrance. We are 12 minutes to Vergennes restaurants and shops, 25 minutes to Middlebury and 45 minutes to Burlington

Top guest favourite
Tiny home in Warren
4.99 out of 5 average rating, 317 reviews

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

Top guest favourite
A cozy cabin, clad in deep red, is nestled among tall trees with vibrant autumn foliage. Large boulders and soft grass surround the cabin, while a brook can be seen flowing gently in the background, creating a serene natural setting.
Cabin in Keene Valley
4.97 out of 5 average rating, 209 reviews

Peaceful Adirondack Cabin right on John's Brook

This cabin is set in a gorgeous, tree-rimmed meadow directly on John's Brook, just 1/2 mile from the village of Keene Valley. Miles of trails are outside your door for your summer or winter enjoyment. Fly fish in the brook just steps from the house or climb Marcy and the range from the front door! The cabin is cozy in the winter with wifi, a fully equipped kitchen and modern amenities. You will enjoy the entire property to yourself in a truly serene setting.

Top guest favourite
A wooden dock extends into calm waters, with a canoe tied alongside. The serene lake reflects the blue sky and fluffy clouds above, creating a peaceful scene ideal for relaxation.
Home in Westport
4.92 out of 5 average rating, 115 reviews

Lakefront w/ dock and sauna in the Adirondacks

Spread out in our rustic but cozy 4 bedroom home! The entire house will be yours to enjoy, along with a dock, sauna, 2 kayaks, 2 SUPs and a canoe. AC and heaters make this a year round retreat. New STARLINK provides fast wifi. The quiet dirt road that leads to the house is perfect for evening strolls, bird watching and kid exploration (bring your bikes!). Local eateries and breweries will keep you fueled for your fun, or just relax on the screened in porch

Top guest favourite
The exterior of the guesthouse is shown, featuring a white wooden facade with multiple windows. A prominent cupola tops the structure, reflecting sunlight under a clear blue sky. Lush green trees and shrubs surround the building, enhancing the serene ambiance of the area.
Guest house in Vergennes
4.98 out of 5 average rating, 135 reviews

Private Guesthouse in the heart of Vergennes

Completed in 2013, the Guesthouse perfectly complements the 1871 Victorian home to which it is attached. Located on Main Street in historic Vergennes, Vermont, our home is one of several fine examples of the architecture of the 19th Century that grace our City. Our thriving downtown is a short walk away, boasting exceptional dining and shopping opportunities. Vergennes is a 20-minute drive away from Middlebury College, and 45 minutes from Burlington.

Top guest favourite
Flat in Charlotte
4.95 out of 5 average rating, 292 reviews

Charlotte Private Studio Apartment with a View

Welcome to our sweet inviting studio apartment. You will enjoy the quiet rural landscape, views of the Green Mountains and Mt. Philo from your bedroom. This east facing large studio offers plenty of light and open concept living. Wide pine floors and comfortable clean surrounds make this the perfect place for two adult guests or a family with children (two adults and one or two children). All are welcome. We look forward to you being our guest.

Top guest favourite
Cottage in Charlotte
4.94 out of 5 average rating, 285 reviews

The Greenbush Barn

Escape to the sanctuary of the countryside yet only steps from a local café. This one-bedroom guest house in a beautifully converted barn sits on six acres with views of fields, forest, and the Adirondacks. Enjoy trails for biking, hiking, and skiing right outside, Lake Champlain just 5 minutes away, plus access to gardens, orchards, and an apothecary garden. Ideal for biohackers, wellness seekers, and anyone craving a restorative homestead stay.

Guest favourite
A charming farmhouse is nestled among autumn foliage, highlighted by vibrant orange and yellow leaves. The structure features a green metal roof and large windows, with a welcoming front porch that complements the natural surroundings.
Guest suite in Elizabethtown
4.91 out of 5 average rating, 132 reviews

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.

Popular amenities for Westport holiday rentals

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  2. United States
  3. New York
  4. Essex County
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