Villa vacation rentals in Woodstock

Private Wing of largest Colonial Mansion in US

Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of Colonial Revival Architecture. Filled with elegance & history, Three US Presidents have slept here. Our 17 Rooms/Suites are individually decorated each with private bathroom & free wireless internet. Set on 14 acres with a tiered terrace offering spectacular views & a custom fire pit. Lots to see in area including Saint-Gaudens Nat'l Park, Quechee Falls, Dartmouth College, etc

Value · Family · Comfort

Cool Mountain House with Lake Access

The house is in a private forest in the White Mountains. Visitors have access to the Mountain Lakes facilities. Kancamagus Scenery Byway, Groton Lake, and Loon are nearby. Well equipped kitchen and a outdoor gas BBQ make gourmet cooking joyful. There are 2 bedrooms upstairs with a Queen bed, and 3 twin beds, and a full bath. A powder room, washer and dryer are provided. HDTV, WIFI/ land-line phone are available. Bring flea spray and a compass, be careful with animals in the woods.

Location · Family · Decor

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.

Family · Location · Skiing

Huge Stunning Mt Snow Villa Jacuzzi/Hot Tub/GameRm

Welcome to Mt Snow Villas!, Your ultimate mountain experience at Mount Snow. This stunning duplex 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!

Value · Family · Hot tub

14-Acre Retreat-Ready Estate Near Ski Resort,

Escape to your private 14-acre mountain estate near Crotched Ski Resort. Retreat-ready with a 400 sq ft training hall & 300 sq ft tea room—ideal for wellness retreats, group stays & family gatherings. This 5-bedroom home features full kitchen and baths, with sunset views, forest trails, and total privacy. In summer, an additional room expands capacity. A rare blend of nature and comfort—30 minutes to Peterborough & Milford.

Location · Family · TV

2-Bedroom Villa w/ King, Queen & Private Balcony

Set among the forested hills of southern Vermont, this two-bedroom villa is the perfect mountain escape for families and small groups. A fully equipped kitchen, dedicated dining area, and a private balcony invite you to unwind after a day in the Green Mountains. On-site amenities include a fitness center, movie theater, game room, and outdoor fire pits — everything you need for a memorable Vermont getaway.

Location · Family · Hiking

Modern 3 Bedroom 4 Bath Villa w HotTub/ back trail

This unique house has a style all its own. with floor to ceiling windows and doors throughout There are 3 levels. top floor has 2 bedrooms with full baths and Hot Tub on the balcony middle level entry; plus Great room: with kitchen, dining, living, activity area with a big table, fireplace and 75 inch television bottom level has 2 bedrooms and 2 full baths

Location · Family · Laundry

Cozy, Comfy & Sunny Renovated Sugarbush Condo

You'll love this sunny stand alone condo/villa with it's proximity to Sugarbush Ski Resort. A short walk to access trails to the lifts and ski home! Located adjacent to the mountain, you'll enjoy this renovated and updated two level space. All new fully equipped kitchen, baths, hardwood floors and Rinnai heater. Outdoor ski locker for all your gear.

Location · Value · Checkout

The Upper Valley Retreat

Upper Valley Retreat: A 20-Acre Vermont Symphony of Light, Land, and Legacy Tucked into the gentle embrace of the Upper Valley, where rolling meadows meet the ancient hush of Brushwood Forest, stands the Upper Valley Retreat — a magnificent 20-acre estate and working apple orchard that feels like a poem written in wood, stone, and sky.

Value · Family · Pool

Villa Near Biking and Hiking Trails

This villa is perfect for your group! Enjoy stunning views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

Family · Location · Pool

Vermont Villa Near the Trails

You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

Location · Cleanliness · Condition

Villa with Games Room + Fitness Center Access

Enjoy stunning views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

Location · Family · View