Villa vacation rentals in Wilton

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Top-rated villa rentals in Wilton

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Superhost

Villa in Bolton

4.62 out of 5 average rating, 13 reviews

Gatehouse Villa at Blue Water Manor w/pool, lake

Welcome to the Gatehouse Villa at Blue Water Manor! Be spoiled w/all the benefits of resort living, while you enjoy the privacy of this unique vacation property. Our 4BR Adirondack-style villa includes 2 decks w/dining, BBQ & a clean, large living space. Bask in the gloriousness of our inviting heated outdoor pool, or enjoy drinks lakeside, splash in the lake and frolic on the playground. Amazing property w/lake views. Enjoy live music & events year round at the Tavern or the Barrel restaurants!

Guest favorite

Villa in Bolton

4.92 out of 5 average rating, 53 reviews

100 yrs old 2024! Historic Musician's Villa Bolton

This truly intriguing turn-of-the century home transports guests to the inspiring mood & enduring character of the great & gracious. Built by a legendary musician’s family w/focus on elegant entertaining, this 100 yr old home is ready for guests after 3 yrs of restoration. Remaining true to original form, guests find showpiece architectural acoustics in great room, elevated framework throughout w/timeless archways, dramatic stairway w/ornate balustrade, romantic rounded walls, relaxing patios.

Guest favorite

Villa in Coxsackie

4.97 out of 5 average rating, 31 reviews

Catskill Villa/Pool with Hudson River View

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

Guest favorite

Villa in Pittsfield

4.93 out of 5 average rating, 30 reviews

Luxurious Berkshire Mountain Retreat!!

Escape to the Berkshires at this 2 acre, private retreat. Gleaming hardwood floors, handmade Amish furniture, large interior and exterior areas for family activities as well as a heated in-ground pool with a slide for the kids that is open during the summer months! Given the 4 bedrooms and additional sleeping areas, this spacious ranch is suited for up to 6-8 guests with the ability to host more (there is a 1 bedroom pool house that can sleep an additional 2 guests for an additional charge).

Guest favorite

Villa in Prattsville

5.0 out of 5 average rating, 24 reviews

LUX MNT 5BR Villa w/Jacuzi/fire pit /Catskill

Your Mountain Escape Awaits at Pratt Villa Escape the bustle & transcend to a relaxing getaway in nature 10 minutes from Hunter & Windham Ski Resorts Breathe the fresh crisp air on 6 acres of land, unwind in a steamy jacuzzi, cozy up by the fire pit or two fireplaces, and get competitive in the game room & bar Immerse yourself in nearby seasonal activities & come home to a spacious, fully-stocked home ready for your group Make the memories of a lifetime w/ all your friends & family year-round

Guest favorite

Villa in Roxbury

4.97 out of 5 average rating, 79 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.

Superhost

Villa in Dover

4.77 out of 5 average rating, 13 reviews

Large Modern Mt Snow Villa Jacuzzi/Hot Tub/Game Rm

Welcome to our gorgeous mountain villa nestled in the heart of breathtaking West Dover just 1/2 mile from Mount Snow! If you're seeking a peaceful escape from the hustle and bustle of everyday life, this spacious villa offers a perfect blend of warmth, elegance and modern comfort, making it the ideal getaway for couples, families, or groups of friends. THIS UNIQUE PROPERTY HAS 6 VILLAS ON ONE LOCATION SO WE CAN HOST UP TO 70 GUESTS FOR GET TOGETHERS OR EVENTS. PLEASE ASK US FOR DETAILS!

Guest favorite

Villa in Winhall

4.88 out of 5 average rating, 16 reviews

Stonehouse at Stratton

Create cherished memories in this unique, family-friendly haven. Designed for entertainment, enjoy a wet bar, pool table, ping pong, darts, and more. Heated floors and Bluetooth sound systems add luxury. Each bedroom has a private bath. The expansive kitchen accommodates the entire family, and a fireplace invites warmth after skiing or boarding. Revel in privacy on 4 acres, with a 2-car heated garage. Only minutes from Stratton, this home offers comfort and leisure in every detail.

Guest favorite

Villa in Pownal

4.97 out of 5 average rating, 37 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

Villa in Cornwallville

4.95 out of 5 average rating, 56 reviews

Catskills Retreat-Pool, Hottub, Bar, Shuffleboard

Welcome to Blue Heaven! A true paradise retreat with 2 houses, your own private inground pool, outdoor shower, pool house, playground, a Speakeasy bar room with billiards, darts, and shuffleboard! Located in the heart of the Catskills just 3 minutes away from Zoom Flume water park and 15-20 minutes away from Hunter/Windham Mountains. Enjoy swimming, roasting smores in the firepit, hiking, skiing/snowboarding, snowshoeing, or soaking up the stars in our hot tub.

Guest favorite

Villa in Stockbridge

4.91 out of 5 average rating, 32 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.

Guest favorite

Villa in New Lebanon

5.0 out of 5 average rating, 10 reviews

Stone Manor: 15 minutes to Tanglewood

New. This property is like nothing you've ever seen. After 2 years of renovation, we welcome you to the Stone Manor --a 150-year-old former Shaker workshop, now a modern home that combines 21st amenities with the historic past of a Shaker settlement. If you are interested in hosting a wedding here, please search The Ruins at Sassafras.