Holiday houses in Plymouth

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

~The ClubHaus~

Appreciate life at our peaceful home away from home in the Vermont Woods... Located a short drive from Killington and Okemo ski mountains, The ClubHaus is the perfect spot to unwind after enjoying four season New England activities. Breweries and great food are nearby in Woodstock, Manchester, and Dorset. Huge fireplace, hot tub, comfortable beds, and lots of thoughtful touches provided to welcome you to the ClubHaus family. Wifi, Netflix, and Disney+ included, no cable. @clubhausvt on IG

Private, Large 4BR home | Pet friendly | 10 Acres

Okemo & Killington Ski House Large 4 bedroom 2.5 bath, 3,000+ sq ft home located close to Okemo Ski Resort and surrounded by 10 acres of land at the end of a private road! This recently renovated home features 3 levels, a large game room, 5 separate sleeping areas and a large covered porch! Enjoy ultimate privacy with proximity to multiple outdoor adventures including skiing, golfing, hiking and mountain biking. Just a short drive to downtown Ludlow and other surrounding stores in Cavendish.

Ludlow Lake & Ski Cottage - Adventure Awaits!

Relax and unwind at our charming cottage directly on Lake Rescue in Ludlow, VT. Enjoy stunning lake views, direct access to water activities (kayaks and paddle boat included!), with close proximity to Okemo Mountain Resort (5 min), Fox Run Golf Club (5 min) and Killington Mountain Resort (15 min - Skyeship). Perfect for your family or a group of friends to take advantage of everything the area has to offer. Our cozy house offers everything you need for your relaxing (or adventurous) getaway!

Cozy Cottage Lakefront

Cozy 3BR Lake home, enjoy year-round adventure & relaxation. Summer-enjoy swimming, paddling, and fishing right from the lake, or roast marshmallows at the fire pit under the stars. Winter, hit the slopes & come home to cozy up in a warm, inviting space. Explore nearby hiking trails, grab a bite at one of the many local restaurants, or plan a day trip to a charming VT town. Whether you're skiing, leaf-peeping, lake lounging, or just unwinding, this home is the ideal base for all-season fun.

8-Acre Retreat Near Killington & Okemo, Sleeps 8

Escape to a private 8-acre retreat in Vermont's Green Mountains—just 7 min from Killington, and 15 from Okemo. This renovated home features a chef's kitchen, organic mattresses & hiking trails. Wake up to mountain views, explore pristine lakes nearby, dine at Long Trail Brewery & farm-to-table spots. Jump on the VAST trailsystem from our backyard. A classic Vermont country store sits across the street. Perfect for skiing, summer adventures & fall foliage. Your four-season basecamp awaits!

Mountain Home: Hot Tub & 9 Min to Skyeship Gondola

Escape to our family-friendly mountain retreat near Killington, Okemo, and Woodstock. Enjoy views, modern amenities, and a cozy atmosphere. Relax on the deck or in the hot tub. With 3 bedrooms and 2 baths, it's perfect for family getaways. Experience Vermont's beauty and adventure! NOTE: ON TOP OF CLEANING FEE FOR THE HOUSE, WE HAVE INCLUDED A FEE OF $209 TO SERVICE HOT TUB BETWEEN EACH GUEST'S USE. THIS IS TO ENSURE CLEAN WATER FOR YOU AND YOUR FAMILY/ GUESTS. THIS IS ACTUAL COST...

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

Thundersnow | Woods • Mountains • Peaceful

Ideally located just 20 minutes to Killington via Bear Mountain and Skyeship, and 10 minutes to the quieter backside of Okemo. Thundersnow is a cozy year-round cabin tucked in the Green Mountains close to Woodstock and Ludlow’s great dining . With a classic stone fireplace, game room, and inviting spaces, it’s the perfect home base for four-season adventures—whether skiing, hiking, or simply relaxing with loved ones and soaking in the peaceful surroundings.

Wooded Vermont Getaway 15 mi to Okemo & Killington

Fall in Vermont starts here. Escape to Plymouth, VT for crisp autumn days, colorful foliage, kayaking on Echo Lake, a small lakeside beach, and scenic biking and hiking trails - all from a peaceful home tucked in the woods. Spend your days exploring the brilliant fall colors, then return to unwind at Hawk Hill Lodge. Perfect for families and groups of friends looking for nature, comfort, and an unforgettable Vermont fall getaway.

Luxury Container Home with Sauna & Heated Pool

Escape to a luxury modern container retreat minutes from Okemo Mountain. Set on 3 private acres with mountain views, this unique getaway features a sauna, heated plunge pool and thoughtfully designed modern interiors. Perfect for skiing, hiking, fall foliage, or relaxing in nature, the home blends comfort, style, and privacy while still being close to restaurants, lakes, golf, and everything Ludlow has to offer year-round.

Secluded 2600 sq ft home 15 min from Okemo+Killington

Welcome to the VT Treehouse in Plymouth, VT. Nestled in a serene mountain setting, this home offers both privacy and convenience. Located just 15 minutes from two of the largest ski resorts in New England—Killington and Okemo; you’ll have easy access to world-class skiing, snowboarding, and winter activities as well as hiking, mountain biking, and exploring nature’s beauty year-round.