Villa vacation rentals in Wilton

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Top-rated villa rentals in Wilton

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Superhost

Villa in Bolton

4.56 out of 5 average rating, 16 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

4.94 out of 5 average rating, 64 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.

Villa in Rupert

4.3 out of 5 average rating, 57 reviews

Gorgeous Victorian-Style House w/ Hilltop Pool!

Nestled in a serene valley of the Green Mountain National Forest and boasting 5 acres of maple tree-laden land, this Victorian home is the place for an unparalleled retreat. The 6-bedroom, 3.5-bath vacation rental was built in 1856 and boasts a perfect blend of old-fashioned charm and modern luxury. Spend your days relaxing at the river on-site, taking a dip in the pool, or roasting s'mores at the fire pit. During winter, curl up with a book in the library and gaze out over a snowy hillside.

Villa in Wilmington

4.95 out of 5 average rating, 20 reviews

Dancing Bear Lodge The Charm of Chimney Hill

Come in and Enjoy yourself at Dancing Bear Lodge.. conveniently located minutes from Downtown Wilmington, Vermont . Dancing Bear Lodge is in Chimney Hill, A 4 season community bordering the Green Mountain National Forest. With its 3 levels of living space It is equipped with all the modern amenities and conveniences. With its 5 bedrooms (4 for use with the rental), 2 family rooms, Loft, and 2 and a half baths, the Lodge can accommodate parties of all sizes about 12 -13 people for sleeping.

Superhost

Villa in Dover

4.78 out of 5 average rating, 9 reviews

Huge Stunning Mt Snow Villa Jacuzzi/Hot Tub/GameRm

Welcome to Mt Snow Villas!, Your ultimate mountain experience at Mount Snow. This stunning villa offers a harmonious blend of luxury, comfort, and convenience, making it the perfect choice for large groups, family gatherings, or anyone seeking an unforgettable escape to the mountains. With the indulgence of a Jacuzzi, hot tub, and sauna, your stay promises both relaxation and rejuvenation. ASK US ABOUT RENTING ALL 6 VILLAS AND HOSTING UP TO 60 PEOPLE FOR YOUR NEXT PARTY OR EXTENDED FAMILY!

Superhost

Villa in Pittsfield

4.92 out of 5 average rating, 37 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 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 Winhall

4.89 out of 5 average rating, 19 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

4.93 out of 5 average rating, 58 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!

Superhost

Villa in Dover

4.77 out of 5 average rating, 13 reviews

Large Updated Mt Snow Villa Jacuzzi/Hot Tub/GameRm

Relax at Mt Snow Villas!! 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.