Villa vacation rentals in The Berkshires

Find and book unique villas on Airbnb

Top-rated villa rentals in The Berkshires

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

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Top guest favorite

A spacious king-size bed is centered against a soft yellow wall, adorned with a decorative moon and floral wall art. Nightstands with lamps are placed on either side, providing additional light and a cozy ambiance.

Villa in Norwich

4.92 out of 5 average rating, 142 reviews

Private Villa 1mi from Casino! New King Bed

Relax at this villa condo that is at the Norwich Inn and Spa. Only 1 mile from Mohegan Sun, this condo a great secret escape after a night of fun at casino. Or as a quaint and quiet spa retreat! This studio condo has an open floor plan. A NEW King-size bed and a pull out couch. Living room suite area. Fireplace and desk area. Full-size kitchen and refrigerator. Private deck, shded by trees. The Club house has shared spa amenities; including fitness, dry sauna, whirlpool, and seasonal pools.

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

4.91 out of 5 average rating, 171 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.

Guest favorite

The outdoor area features a paved patio with several black metal tables and chairs, surrounded by colorful flower planters. In the background, a sparkling swimming pool is enclosed by a white fence, with sun loungers and greenery complementing the peaceful setting.

Villa in Norwich

4.89 out of 5 average rating, 400 reviews

Peaceful Spa Escape minutes to Mohegan Sun Casino

CLEAN-COZY-SAFE-PRIVATE-SPA-WOOD BURNING FIREPLACE Just 3 minutes from Mohegan Sun Casino! This 1 bedroom unit is perfect for solo explorers, couples, girls getaways, or small families looking to experience the excitement of the Casino, while also getting away from it all. Amenities include; 2 seasonal outdoor saltwater pools, jacuzzi, cardio room, and sauna! Beautiful shared grounds w/ The Spa at Norwich Inn and The Norwich Golf Course. Laundry facility onsite. Plenty of free parking!

Guest favorite

Adirondack chairs are positioned on a grassy area by the water, surrounded by autumn foliage. Gentle waves lap against the shore, while trees with colorful leaves frame the serene view of the river and distant houses.

Villa in New London

4.86 out of 5 average rating, 29 reviews

Waterfront Holiday Vacation Villa New England

Have fun with the whole family at this stylish VILLA with water (kayak) access to Ocean State Beach Park and a 4 minute drive to the quaint Waterford Beach. This idyllic leisure home has everything you need to enjoy your gateway. SECLUDED setting with 300 ft of waterfront access for kayaking , fishing. Sauna, bicycles, waterfront gazebo with fire pit , basketball hoop and hammocks. All spaces are newly renovated and tastefully decorated. New fully stocked kitchen . Close to Mystic - Foxwoods

Guest favorite

The exterior of the house features a multi-story design with a large wooden deck overlooking the surrounding greenery. A circular fire pit with seating is visible in the backyard, complemented by a fenced area and a mature tree. The sky is partially cloudy with blue hues.

Villa in Coxsackie

4.89 out of 5 average rating, 47 reviews

5-BR Villa with Pool and Dog Friendly!

Welcome to Hudson View Villa! Relax with family or friends at a hilltop property overlooking The Hudson and Berkshires. Hudson View House offers over 2900 sq ft of gorgeous luxury space with views of the Hudson and Berkshires virtually from every room. The scenic views of the surroundings, breathtaking sunrises and sunsets will want you never to go home! Heated swimming pool now Open ( May - Sep/October). Propane grill on back deck overlooking Hudson River. Tesla charging- bring own adapter

Superhost

A modern kitchen is presented, featuring wooden cabinetry and a large granite island with seating for four. Stainless steel appliances are visible, including an oven and a refrigerator. Soft yellow lighting creates a warm ambiance, complementing the hardwood floors.

Villa in Charlton

4.78 out of 5 average rating, 67 reviews

Winter Home near TreeHouse Brewery with King Beds

Bring the whole family to this lovely villa with lots of free parking and multiple comfy King Beds. This Villa seats on 1 Acre in a really residential and quiet neighborhood in Charlton MA. The property boasts of a spacious backyard with a private play ground for kids and a private pool with a large deck. It's less than 10 minutes away from the Treehouse brewery. The Heritage Country Club golf course is about 10 minutes from the Villa. There are several lakes within 20 minutes from the Villa.

Superhost

A charming two-story villa is set amidst lush greenery, showcasing light blue siding and large windows. A circular driveway leads to a spacious garage, while outdoor seating is arranged with four chairs near a small table, inviting gatherings in the serene surroundings.

Villa in Bloomingburg

4.8 out of 5 average rating, 59 reviews

Spacious 6BR Villa | Serene Scenic Mountain Escape

Escape to this spacious 6BR villa, a serene mountain retreat with scenic views. This peaceful getaway is perfect for families and groups. Located approximately 1 hour from the George Washington Bridge, it offers comfortable interiors, a well-equipped home, and ample outdoor space. Explore nearby hiking trails and relax in a tranquil setting just minutes from local attractions. Unwind and experience nature in every direction. Your peaceful mountain escape awaits—BOOK NOW FOR A SERENE GETAWAY!

Top guest favorite

An inviting seasonal outdoor pool is framed by a spacious patio area, with multiple lounge chairs arranged around it. The pool is bordered by trimmed grass and green landscaping, while large windows provide a view of the adjacent building, enhancing the tranquil setting.

Villa in Norwich

4.97 out of 5 average rating, 113 reviews

Two floor Norwich Spa Villa near Mohegan Sun

Penthouse 2 floor villa located on the grounds of the beautiful Norwich Spa. Guests can enjoy the seasonal outdoor pool, hot tub and fitness center on the property. Restaurants and juice bar located inside the Inn. Spa amenities not included with your stay, but we highly recommended visiting! Great location, just minutes away from Mohegan Sun! Gambling, great restaurants, concerts and arcades. There's something for everyone there! Also across the street from the Norwich Golf Club.

Top guest favorite

Villa in Roxbury

4.98 out of 5 average rating, 95 reviews

Your tranquil escape w/ endless mountain views.

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.

Top guest favorite

Villa in Kerhonkson

4.97 out of 5 average rating, 253 reviews

Luxury Villa Escape w Private Yoga Studio

Escape to a secluded luxury villa nestled in a serene pine forest with mountain views. This retreat offers a private yoga studio, jacuzzi in the master bedroom, and a spacious deck for stargazing. Ideal for wellness retreats, romantic escapes, and family gatherings, the villa includes high-speed Wi-Fi, a fully equipped kitchen, premium bedding, and thoughtful amenities. Explore nearby hiking trails like Vernooy Falls, Minnewaska Park, and visit cultural spots like Woodstock, NY.

Guest favorite

Villa in Pownal

4.94 out of 5 average rating, 69 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!

Top guest favorite

An aerial view showcases an expansive backyard framed by autumn foliage. A stone patio is surrounded by neatly trimmed shrubs and decorative plants. Wooden lounge chairs are positioned in a tranquil setting, complemented by a water feature and a spacious area for outdoor gatherings.

Villa in New Haven

4.98 out of 5 average rating, 128 reviews

Dove Haven | Find Your Peace

Best & most beautiful Airbnb in New Haven. No expense has been spared in our well-appointed architectural gem just minutes from downtown New Haven. Luxurious amenities and curated design elements await you. Take lunch in the light-filled sun porch, unwind in the 8-person hot tub, move your body in the equipped home gym, or entertain in the private Zenscape garden. Endless possibilities exist at Dove Haven. You will leave feeling relaxed, inspired, and rejuvenated.