House holiday rentals in Sharon

4.94 out of 5 average rating, 362 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

4.96 out of 5 average rating, 142 reviews

A charming red cottage is surrounded by trees displaying autumn foliage. The structure features white trim and a star accent on the wall. A fenced garden area lies in front, complemented by neatly arranged shrubs. A driveway leads to the entrance, enhancing accessibility.

Home in Amenia

The Red Country Cottage

Perfect getaway in this countryside cottage nestled in nature but walking distance to town center. Spend some relaxing time watching the creak run by, walk or bike (provided/bring own) on the 26mi flat scenic Harlem Valley Rail Trail from the cottage. Enjoy the evening sitting by the fire/comfortable patio. Visit the 60’s themed movie theater and restaurant walking distance, near by brewery/winery/cafe/restaurants, wedding venues, Lime Rock Racing, skiing. Direct train to Wassaic from MetroNorth

A cozy wooden cabin is surrounded by lush greenery, featuring a welcoming porch with a sturdy railing. Sunlight casts gentle shadows across the textured facade, showcasing the natural wood shingles and spacious windows. A well-kept lawn enhances the inviting atmosphere.

4.85 out of 5 average rating, 110 reviews

State Forest Getaway

Enjoy our Mountain getaway for year round fun! There are lots of activities close by-Mohawk Ski Mountain, Indian Lake and historic Covered Bridges! Hike in the backyard, cool off in the creek or relax in front of the Wood-burning fireplace or get the whole family together for a fun BBQ on the outdoor deck. We have 4 comfortable bedrooms plus daybed room and 3 bathrooms and a fully equipped Chefs Kitchen. The living room is great for lounging and perfect a movie night watched on the projector

4.92 out of 5 average rating, 426 reviews

A spacious deck is presented with cushioned chaise lounges and a dining table under a red umbrella. The surrounding trees provide shade, enhancing the outdoor living experience. Sunlight filters through the leaves, creating a peaceful ambiance.

Home in Millerton

Deluxe Mtn Loft, self checkin/out, fast WiFi

Atop Silver Mountain, outdoor living in the private forest overlooking the Hudson Valley. Enjoy nature with 200+ bird species, yoga, meditation, or quiet reading in the fresh, crisp mountain air Revel in privacy and tranquility, yet stay connected with 500Mbps WiFi, a 60” HD TV and wood burning fire stove. Unwind on a huge deck with cushioned chaise lounges for stargazing and Bar BQ Grill. Enjoy picnics by the private pond, deck, chaise lounges, a dock, paddle boat, fishing and fire-pit!

5 out of 5 average rating, 103 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

Boulder Tree House 🌲🌲🌲 FRESH AIR • SMOKE FREE • ALLERGY FREE Early Check In & Late Check Out! Boulder Tree House is an Inhabitable Work of Art, created by owner architects. The design is based on organic and innovative blending of natural elements and environmentally conscious technology, creating a happy and healthy living space. Boulder Tree House is ideal for a couple looking for a exciting, romantic and unique experience. The space can also comfortably accommodate a 3rd person.

4.83 out of 5 average rating, 414 reviews

A charming two-story blue house features a vibrant red front door, surrounded by colorful autumn foliage and a spacious lawn. Gravel paths lead to the entrance, highlighting the inviting exterior and nearby greenery.

Home in Litchfield

Rustic - Modern - Hot Tub - Mohawk Mountain - BBQ

Enjoy the comfort of home with air conditioning, heating, dedicated workspace, TV, and Wi-Fi. Cook your meals in the fully-stocked kitchen with all the essentials. Pamper yourself in the private bathtub or shower with provided body soap, shampoo and conditioner. Relax in the hot tub or lounge in the backyard with an outdoor dining area, bbq, patio, and fire pit. 3 Min - Litchfield Town 4 Min - Arethusa Dairy farm 5 Min - White Memorial Conservation Center 16 Min - Mohawk Mountain Ski Area

A newly remodeled kitchen showcases white cabinets complemented by a marble countertop and a decorative backsplash. A rustic wooden dining table with chairs is positioned near a window, while a vibrant area rug adds warmth to the space. Modern appliances are neatly integrated into the design.

4.98 out of 5 average rating, 163 reviews

Under Mountain House

Our home is designed to be your home away from home! It has been newly renovated with comfort in mind so you can enjoy your stay in the Berkshires. Whether you are here to hike parts of the Appalachian Trail, stroll into town for a leisurely meal, enjoy Lime Rock Race Track or explore the many surrounding New England towns you can be assured you will always have a comfortable home to come back to!! My home is located just a 3 minute walk to the center of town and the historic White Hart.

4.9 out of 5 average rating, 168 reviews

A rustic cottage is nestled among vibrant green trees, surrounded by a spacious lawn. A large deck extends from the cottage, offering a quiet retreat. The scene captures the tranquility of nature, with dappled sunlight filtering through the leaves.

Home in Sharon

Nature Cottage w/ Private Path to River Access

Summertime in beautiful Sharon! Comfortable, rustic cottage with fire-pit, wood-burning stove, large deck for star-gazing, 4 acres, a brook and private path to 200' Housatonic River frontage. So cozy! In lovely Litchfield Hills, covered bridges, lake swimming, restaurants, the Appalachian trail and hiking trails, ski areas, Audubon Center, Clarke Outdoors tubing/ kayaking and Ellsworth Farms fruit picking. Near Millerton, Kent, Great Barrington. Lake beach pass included in the rental.

4.98 out of 5 average rating, 126 reviews

A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.

Home in Kingston

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

The farmhouse exterior displays a yellow façade with white trim and bright blue front door. Multiple large windows allow natural light to fill the home. A small seating area with two chairs and surrounding greenery adds to the inviting appearance of the property.

4.99 out of 5 average rating, 140 reviews

The Farmhouse

Enjoy staying at our charming Farmhouse in the heart of our working dairy farm. Our farm sits on some of the most beautiful hills in Cornwall with the famous Gateway to Cornwall view where you can see our dairy cows grazing in the grandeur of nature. Come say hello to the cows in the barn during milking or watch the herd cross the road evoking sites you might expect to see in small European farming villages. You'll likely see us on our tractors bringing hay and water to our cows!

4.99 out of 5 average rating, 300 reviews

Home in Lee

Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

The interior space showcases exposed wooden beams and a bright, open layout. A comfortable seating area is positioned near large windows that provide natural light and views of the surrounding trees. A round dining table is visible, accompanied by a set of stylish chairs.

4.91 out of 5 average rating, 281 reviews

Secluded modern forest cabin with private brook

Renovated cozy cabin (orig 1930s) with modern interior. Two bedrooms, new kitchen & bathroom, overlooking a beautiful private brook and forested hill. Minutes drive to the general store & Kent Falls, 10 minutes from fantastic restaurants, Mohawk Ski Resort & summer activities like swimming & kayaking. Great hiking trails and close to the Appalachian Trail. High speed internet, Netflix, and a deck with outdoor seating. Instagram @GunnBrookCabin

Popular amenities for house rentals in Sharon

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 171 reviews

A spacious cedar hot tub sits peacefully outdoors, surrounded by a natural setting of trees and open space. Bubbles rise from the water, creating a relaxing atmosphere. Clear blue skies are visible above, enhancing the tranquil environment.

Home in Hudson

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

4.94 out of 5 average rating, 139 reviews

The spacious bedroom features a large bed with a geometric patterned duvet and plush pillows. Flanking the bed are two nightstands with lamps. A cozy area rug complements the hardwood floor. Robes are hung on the wall, and a doorway leads to the en suite bathroom.

Home in Saugerties

Bluestone Escape - Where everyone is at home.

4.87 out of 5 average rating, 177 reviews

An open living space is visible, featuring wooden beams that create a warm atmosphere. The dining area is filled with natural light, showcasing a wooden table surrounded by chairs, with modern light fixtures above. A staircase leads to the upper floor, enhancing the spacious design.

Home in New Paltz

Scenic River View Escape | New Paltz

5 out of 5 average rating, 157 reviews

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills

4.93 out of 5 average rating, 196 reviews

A cozy living room features exposed wooden beams and warm wood-paneled walls. A stone fireplace is centrally located, with a basket of wood beside it. A rug with rich colors lays under a wooden table, surrounded by comfortable seating, inviting a relaxed atmosphere.

Home in Litchfield

Stunning Views, Bucolic Bliss in 1790s Farmhouse

5 out of 5 average rating, 106 reviews

A bright living area features large windows that invite natural light. The space includes a dark sofa, a vibrant yellow armchair, and a soft, patterned area rug. A coffee table is centrally placed, accompanied by a small side table with a decorative lamp.

Home in Taghkanic

Sunbeam Lodge: Pool+Hot Tub, 50 Acres, ‘70s Oasis

4.79 out of 5 average rating, 112 reviews

The exterior of the house showcases a combination of stone and brick, framed by well-kept landscaping. A mature tree offers shade in the front yard, while a pathway leads to the entrance. The roof features a peak with multiple gables.

Home in Kingston

Hudson River views with pool and hot tub

4.95 out of 5 average rating, 288 reviews

A wooden lounge chair is positioned near a serene saltwater pool, surrounded by lush greenery. The pool's clear water reflects the inviting outdoor space, which is complemented by concrete paving and a manicured lawn.

Home in Cottekill

Peace & Privacy - High Falls (hot tub & salt pool)

Weekly house rentals

A spacious living area is illuminated by natural light, featuring large windows that offer views of the surrounding trees. Comfortable seating options include a sectional sofa and two round ottomans. A modern dining table for six complements the open layout, creating an inviting atmosphere.

4.99 out of 5 average rating, 75 reviews

Curated Contemporary for lakes, forest & ski hills

An aerial view captures the modern structure with large floor-to-ceiling windows, showcasing a warm glow from the interior lights. The building is surrounded by lush greenery and features a terrace adorned with chairs, providing expansive outdoor space for relaxation.

5 out of 5 average rating, 3 reviews

Lakefront Escape | Private Dock Hot Tub & Views

4.88 out of 5 average rating, 43 reviews

The house features a dark wooden exterior and large windows that invite natural light. Surrounding greenery adds to the serene atmosphere, while a manicured lawn provides space for outdoor activities. A stone path leads to a welcoming entryway, emphasizing the connection to nature.

Home in Sharon

Beautiful sun filled cottage in the woods

An open-concept living area features a modern teal sofa and a light gray lounge chair, both positioned on a textured area rug. Sunlight pours in through large windows, illuminating natural wood flooring and creating a bright and inviting space. A cozy wood stove is visible in the corner.

4.91 out of 5 average rating, 35 reviews

Gunn Brook Mountain House

5 out of 5 average rating, 39 reviews

A well-maintained home is set against a backdrop of green lawns and trees. The exterior features a patio area with seating, framed by vibrant landscaping. The sky displays a mix of clouds, with sunlight illuminating the space.

Home in Millerton

Modern Ranch Retreat in Hudson Valley

5 out of 5 average rating, 12 reviews

Home in Lakeville

Quiet home with a running brook.

5 out of 5 average rating, 30 reviews

A modern dining area is highlighted by a long wooden table surrounded by six black wire-frame chairs. A vase of fresh yellow tulips sits at the center, while large windows frame views of the outdoor landscape, filling the room with natural light.

Home in Millerton

Gorgeous Modern New Ranch near Rail Trail!

5 out of 5 average rating, 3 reviews

Longpond Farm House and Loft

Private house rentals

4.93 out of 5 average rating, 43 reviews

A light and airy living room features a large sectional sofa and a patterned rug underfoot. A stone fireplace is situated next to a stylish armchair, while artistic wall decor adds character. Large windows provide natural light and views of the surrounding landscape.

Home in Goshen

Halo Hollow Haus - Litchfield Lake & Ski Haven

5 out of 5 average rating, 14 reviews

An open kitchen features a large antique wood island adorned with a colorful rug and fresh produce. Natural light floods in through mullioned windows, highlighting the patterned tile floor and stylish bar stools. Vintage pendant lights add a touch of charm above the island.

Home in Pine Plains

Stunningly Designed Historical Icon w/ Hot Tub

5 out of 5 average rating, 30 reviews

The cottage features a covered porch with several blue chairs arranged for relaxation. The exterior showcases light-colored siding, complemented by dark trim. A well-maintained lawn stretches around the property, with trees providing shade and a small shed visible in the background.

Home in New Milford

Cozy cottage

5 out of 5 average rating, 89 reviews

A cozy living room is furnished with two gray sofas and a patterned armchair. A wooden coffee table sits in the center, complemented by a decorative plant. Natural light enters through large bay windows, highlighting the space's warm, neutral tones.

Home in Sherman

Slice of Paradise in the Country

4.94 out of 5 average rating, 52 reviews

A two-story yellow house features a classic entrance with a covered porch. Flanking the doorway are two large windows on each side, allowing for ample natural light. A pair of white adirondack chairs sits in front, and pumpkins adorn the steps, enhancing the welcoming feel.

Home in Kent

Charming Home in Kent

4.74 out of 5 average rating, 245 reviews

A historic farmhouse, characterized by its gray siding and white trim, features a symmetrical facade with large windows. Greenery surrounds the entrance, highlighting a red door and flower boxes under the windows. The building is topped with a gabled roof and flanked by tall trees.

Home in Warren

Rustic Farmhouse; Cozy Apartment; Litchfield Cnty

4.69 out of 5 average rating, 70 reviews

A simple country house is set back from the road, featuring a covered front porch with steps leading up. A brick chimney adds a rustic touch, while expansive green grass surrounds the property. Trees line the perimeter, offering a serene country setting.

Home in Sharon

Cottage in the Berkshires 2 hrs NYC