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Villa vacation rentals in Berkshires

Find and book unique villas on Airbnb

Top-rated villa rentals in Berkshires

Guests agree: these villas are highly rated for location, cleanliness, and more.

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Guest favorite
A private outdoor area features a spacious swimming pool with a connected spa, surrounded by greenery. Two decorative lion statues flank the pool entrance. Lounge chairs and a gazebo provide additional relaxation options under a sunny sky dotted with clouds.
Villa in Columbia
4.92 out of 5 average rating, 109 reviews

Breathtaking home with unforgettable views & pool!

This perfect peaceful and private home on 5 acres is great for unwinding & relaxing whether it is enjoying the day by the incredible pool/spa or star gazing at night. far from the noise and pollution of city life. You can spend a weekend or a week away from work life because you deserve it. Close to Foxwoods casino and Mohegan sun casino, super Walmart and other stores. please let us know before booking more than 4 people whether it is just for the day or night or both. no loud music no parties

Guest favorite
A stone patio surrounds a tranquil pool, where light blue lounge chairs are arranged under a white umbrella. In the background, a separate building is visible, surrounded by lush greenery and trees, creating a serene outdoor setting.
Villa in Morris
4.89 out of 5 average rating, 134 reviews

LuxeCompound-HotTub Pool Sauna Treehouse Gamebarn

Serene, elegantly appointed 19th century compound, fully modernized and set on the edge of a 50 acre land preserve next to boat friendly Bantam Lake. Located in the rolling hills of Litchfield County this expansive home has four buildings and every amenity: pool, hot tub, heated gym, cedar sauna, central AC, 2 chef’s kitchens, game barn, primary suite with wb fireplace and soaking tub, a pool house guest suite with steam shower, & treehouse w/ slides & a swing set built on a 300yr old oak tree.

Guest favorite
A black wooden house is positioned dramatically over a cascading waterfall, surrounded by leafless trees. The structure features a spacious deck with wooden railings, offering scenic views of the flowing water below and neighboring houses visible in the background.
Villa in Woodstock
4.9 out of 5 average rating, 204 reviews

The Falls

A secret treasure in the heart of Woodstock. This waterfall escape is tucked up in the center of town with incredible privacy, a private deck overlooking the waterfalls and located on the entire first floor just up a flight of stairs of the main house. Enter through your own private deck overlooking the waterfalls. Walk to all the great restaurants, galleries and shops around Woodstock. A truly magical experience. amidst the trees on top of the waterfalls. The most sought after Airbnb in town.

Superhost
A collage featuring four aspects of the home. The top left displays a cozy living area with a fireplace and comfortable seating. The top right shows a hot tub surrounded by a wooden fence. The bottom left highlights a retro arcade setup with colorful lighting. The bottom right features a dining table set for a meal.
Villa in Kerhonkson
4.89 out of 5 average rating, 109 reviews

Luxe Mountain Getaway|Fire Pit|Arcade|Hot Tub|Pool

Enjoy a luxury nature escape at Boho Chic Villa, under 2 hours’ drive from New York City. This cozy home offers three bright bedrooms, an elegant full kitchen, and unmatched outdoor space. Take a splash in the pool, soak in the hot tub, or make s’mores around the fire pit. Your stay is sure to be an extraordinary experience for the whole family. 6 Min Drive to Minnewaska State Park 8 Min Drive to Kelder’s Farm 10 Min Drive to Stony Kill Falls Experience Kerhonkson With Us & Learn More Below!

Top guest favorite
A wooden table is set for outdoor dining, surrounded by woven chairs. Two lanterns are placed in the center, with a large umbrella providing shade. Views of the tranquil water and lush greenery are visible in the background, creating a serene setting.
Villa in Waterford
5 out of 5 average rating, 23 reviews

Spacious Waterfront Getaway

Relax on the water and experience the outdoors with your family and friends. Enjoy expansive views of the Niantic estuary, kayak from the private beach. BBQ and enjoy a relaxing day on your chaise, overlooking the water. Enjoy time together in comfortable living areas with everything you need. Whether you're planning a weekend getaway or a longer vacation, enjoy charming coastal towns, pristine beaches, natural beauty, and culinary delights less than 15 minutes away from your comfortable home.

Top guest favorite
A contemporary living room features an 18-foot tall cathedral ceiling and a mix of stylish furnishings. Two couches are positioned around a circular blue rug, while a serene hammock hangs from the ceiling. A fireplace serves as the focal point, with plants adding life to the space.
Villa in Newburgh
5 out of 5 average rating, 76 reviews

Ultra Modern Private Oasis with River Views

Step into your brand new, ultra-modern secluded oasis with picturesque views of the Hudson River and Valley. The Balthus Haus was designed and built with sheer comfort, stylish aesthetics, and progressive functionality as the guiding tenets. Nestled high into the hillside the Haus maximizes 360 degrees of privacy and is surrounded by nature. Inviting and pleasant all year round with central AC and radiant heated floors throughout the living areas. Easily get away from NYC only 1.25 hours away!

Top guest favorite
A private deck features a round hot tub set against a backdrop of lush green trees and rolling mountain views. A wooden lounge chair is positioned nearby, providing a space for relaxation and enjoyment of the serene natural surroundings.
Villa in Roxbury
4.98 out of 5 average rating, 102 reviews

Your tranquil escape, and is also for sale.

Experience unparalleled luxury, where opulent decor and furnishings from around the world create a unique haven. The upper level includes two bedrooms and 2.5 bathrooms, a master suite with a jacuzzi. Stunning mountain views from the hot tub, unwind by fireplaces, or discover serenity in the meditation chapel. For an additional cost, the downstairs area offers an apartment and office. The villa effortlessly blends comfort and sophistication, providing the perfect retreat for any purpose.

Guest favorite
An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.
Villa in Pownal
4.94 out of 5 average rating, 88 reviews

Vermont Vacation Villa—Grapevine Getaway

Nestled in the stunning natural beauty of Vermont, this striking villa offers the perfect escape from the hustle and bustle of everyday life. Surrounded by rolling hills, and picturesque countryside, this home is a paradise. Whether exploring the area's cultural institutions, immersing yourself in the natural beauty of Vermont, or relaxing and unwinding with family and friends, this vacation home is the perfect retreat. Experience the magic of this beautiful area for yourself!

Guest favorite
A bright living room features a comfortable seating area with a white sofa and chairs. A large artwork is mounted above a fireplace, while a decorative mirror is positioned nearby. Natural light enters through a large window, revealing expansive views outside.
Villa in Hudson
4.91 out of 5 average rating, 45 reviews

Mountain-View Retreat @ Hudson

Experience breathtaking mountain views from this designer-decorated home in the heart of Hudson.. Inside, enjoy a full game room, in-house laundry, and on-premise parking. The fenced property offers complete privacy with a security system. Walk to downtown Hudson (5 minutes drive), access nearby track and tennis courts, or take a short drive to Catskills trails, Bash Bish Falls, and Hunter Mountain. Ideal for relaxation and adventure, with easy Amtrak access nearby.

Top guest favorite
Villa in Danbury
4.95 out of 5 average rating, 111 reviews

Luxury Lakeside • Hot Tub, Pool & Chef Kitchen

☞ Hot tub & Heated Pool (May-Oct) ☞ Lakeside with incredible views ☞ Perfect for families ☞ Fully stocked Chef's Kitchen ☞ Covered outdoor patio dining ☞ Ridiculously comfy beds ☞ EV Charger ✭“This was such a beautiful property, it was everything posted on the site and then some! ” ☞ Trampoline + Hoop ☞ Super-fast WIFI ☞ 75" TV + Projector ☞ Weber grill (direct gas) ☞ Espresso Machine ☞ Washer + Dryer ☞ Sonos ☞ 2 Fireplaces + Firepit ☞ Hikes directly from house

Top guest favorite
The villa's exterior showcases a large three-story structure, adorned with white siding and multiple windows. A spacious deck leads to the front entrance, framed by greenery from surrounding trees. The sky above is partly cloudy, providing a serene backdrop.
Villa in Stockbridge
4.95 out of 5 average rating, 57 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and blackberry patch surrounded by 25 acres of woods. Walking paths reveal rocky knolls and paths circling through pine and maple trees. The private estate has ample space for a retreat, a workshop or just family togetherness in a beautiful place, far from the madding crowd but close to highways, shopping, spas and everything you might need.

Top guest favorite
Villa in Kerhonkson
4.97 out of 5 average rating, 288 reviews

Villa Retreat: Yoga Studio, Theater, EV Charger

Multi-level forest villa retreat in the Gunks, perfect for wellness escapes, creative retreats, or group getaways. Enjoy a private yoga studio, 110" home theater, EV charger, handmade furnishings, Casper and Nectar premium mattresses, and inspiring original art. Surrounded by forest with decks, private nooks, and cozy lounges, this beautifully designed home blends boutique comfort with spacious indoor-outdoor flow.

Popular amenities for Berkshires villa rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Private villa rentals

Superhost
An open concept living area is presented, featuring a large dining table adorned with a floral centerpiece. A modern kitchen is visible in the background, equipped with white cabinetry and stainless-steel appliances. A comfortable seating area is highlighted by a green sofa and a mounted television.
Villa in Bridgeport
4.5 out of 5 average rating, 14 reviews

Cheerful 3-bedroom vacation home with fire pit

A modern villa is set against a serene backdrop, featuring large windows that reflect the landscape. A small bridge leads over a private fishing pond, while trees line the property, inviting a peaceful atmosphere. Bright red doors stand out against the neutral exterior.
Villa in Port Jervis
4.65 out of 5 average rating, 65 reviews

Mountain Getaway by Legoland and Delaware River

A view of the resort's outdoor area showcases green tennis courts surrounded by trees and grass. Multiple buildings featuring wooden exteriors are positioned in the background, with gentle hills covered in lush greenery rising beyond.
Villa in South Lee
4.77 out of 5 average rating, 135 reviews

Villa with Access to Amazing Amenities!

Guest favorite
The historic estate is elegantly illuminated at dusk, showcasing its white exterior and traditional architectural details. The main entrance, framed by green shutters and a vibrant red door, is surrounded by manicured landscaping and soft outdoor lighting, enhancing the estate's charm.
Villa in Goshen
5 out of 5 average rating, 10 reviews

Goshen Retreat w/ Hot Tub & Fire Pit near Legoland

Guest favorite
A spacious entertainment area is featured, showcasing a wet bar and a pool table, with comfortable seating arranged around the space. Large windows allow natural light to fill the room, while a television is mounted on the wall. A dining table is visible in the corner.
Villa in Winhall
4.91 out of 5 average rating, 23 reviews

Stonehouse at Stratton

Superhost
Villa in West Kill

Two entire houses on Hunter Mtn with Creek

An arcade room features a variety of games, including a vibrant green air hockey table at the center. Nearby, colorful games and a television surround comfortable seating, providing an inviting space for entertainment and enjoyment.
Villa in South Lee
4.78 out of 5 average rating, 36 reviews

Spacious Villa with Access to Various Amenities!

A vibrant game room is illuminated with colored LED lighting, featuring a billiards table with a colorful set of pool balls. Adjacent to the table is a foosball table, and a retro sign adds a decorative touch to the space.
Villa in Warwick
4.63 out of 5 average rating, 173 reviews

Family Fun Getaway near Cascade Lake in Warwick NY

Luxury villa rentals

A graceful seating area features an elegant couch adorned with a decorative cushion, complemented by a rich yellow table covering. A potted orchid and other greenery are positioned near the window, which is draped with light, flowing curtains. A decorative rug adds warmth to the space.
Villa in Ames

Hands Down

An airy great room features a striking red accent wall, complemented by wooden beams and large windows allowing natural light to fill the space. A stylish black sofa is positioned near a fireplace, with a collection of plants and bookshelves adding to the decor.
Villa in Newburgh
4.65 out of 5 average rating, 20 reviews

Exquisite Modernism overlooking the Hudson

Superhost
The country-side home features a charming exterior with a blue metal roof and inviting front porch. Lush greenery surrounds the property, enhancing the tranquil outdoor setting. A stone pathway leads to the entrance, framed by manicured hedges and flower beds.
Villa in New Paltz
4.87 out of 5 average rating, 30 reviews

Country home with rock climbing gym, pond & creek.

Guest favorite
A stone fire pit is surrounded by colorful adirondack chairs, offering a view of a two-acre lake and lush greenery. A hammock is situated nearby, with a pedal boat visible on the water. The scene is accented by a partly cloudy sky.
Villa in East Meredith
4.91 out of 5 average rating, 32 reviews

Private oasis in the Catskills, The Stewart Manor

Superhost
An inviting living area features a stone fireplace accompanied by a large flat-screen TV. Colorful artwork and decorative accents include modern furniture and plush seating. Large windows allow natural light to fill the space, while a dining area is visible in the background.
Villa in Bridgeport
4.81 out of 5 average rating, 16 reviews

Indulge in Prime Luxury 3BR 3-7 Guest

A heated pool is surrounded by a spacious patio, featuring a smooth stone surface. The pool is bordered by a safety fence, and lush greenery is visible in the background, providing a serene outdoor setting for relaxation.
Villa in Woodridge
4.35 out of 5 average rating, 20 reviews

Best pool in town Davos

An aerial view showcases a modern home with large floor-to-ceiling windows. A rounded fire pit surrounded by seating is visible in the yard, along with an in-ground heated pool. Lush greenery and trees frame the property, highlighting the spacious outdoor area.
Villa in Monticello

Contemporary Lake Front - 5 Acres!

Superhost
The grand estate features a symmetrical façade with large windows, a central entrance adorned with double doors, and a balcony above. Surrounding flowerbeds add color to the landscape, while the mature trees provide a natural backdrop. A gravel path leads up to the entrance.
Villa in Fort Plain

Whistling Hills Estate

Villa rentals with a pool

Guest favorite
The outdoor heated swimming pool is framed by a stone patio, with a shaded pergola alongside. Sunlight reflects off the clear water, capturing the serenity of the surrounding landscape and distant hills at sunset.
Villa in Coxsackie
4.91 out of 5 average rating, 58 reviews

5-BR Villa with Pool and Dog Friendly!

Guest favorite
A tranquil winter scene depicts a classic farmhouse and a red barn surrounded by a blanket of fresh snow. A path is visible in the snow, leading toward the inviting buildings, and tall trees are present in the background, adding to the serene atmosphere.
Villa in Wingdale
4.88 out of 5 average rating, 16 reviews

Beautiful farmhouse nature escape 90 min from NYC

Guest favorite
An aerial view of the property reveals a spacious lawn surrounded by manicured gardens and trees. The charming farmhouse is visible along with a patio area, swimming pool, and additional buildings, set against a backdrop of vibrant greenery under a clear blue sky.
Villa in Putnam Valley
5 out of 5 average rating, 18 reviews

Bird Haven Farmhouse: Luxury Villa Living w/ Pool.

Top guest favorite
The entrance of the historic home is framed by carefully manicured hedges and trees. A path leads to an elegant front door, flanked by large windows. Decorative wall lanterns add charm to the exterior, capturing the welcoming essence of the property.
Villa in Longmeadow
5 out of 5 average rating, 59 reviews

Comfort and Luxury - 180 year Old Gothic Estate

A spacious hot tub sits on a wooden deck, surrounded by snow-covered trees and greenery. Steam rises gently from the water, creating a serene atmosphere on a winter day.
Villa in Hensonville
4.92 out of 5 average rating, 64 reviews

Private Pool, hot tub & Bar open!Windham Art House

The spacious home, framed by lush greenery, features large windows reflecting blue skies. A stone wall borders the in-ground saltwater pool, with two lounge chairs positioned nearby. The patio area includes a dining set under a shaded umbrella, creating an inviting outdoor space.
Villa in Garrison
4.95 out of 5 average rating, 98 reviews

Serene and Peaceful - Surrounded by Nature

Villa in Woodstock
4.85 out of 5 average rating, 81 reviews

Prime Woodstock Luxe 5BR-3Baths-Heated Ing Pool

Villa in Goshen
4 out of 5 average rating, 3 reviews

Pool, Fire Pit Bedroom & Alaska King – Sleeps 16

Destinations to explore