31 results - closest to you first 📍
The Weston
In the village of Weston, in the Okemo Mountain Resort area, The Weston is the Sharp family's latest inn — the same family behind New York's Carlyle and Gramerc...
Apple Knoll Inn and Cottages
This 1830 Georgian timber-frame house in Weston began life as a sheep farm and grew into the Apple Knoll Inn — today it rents as a whole-house vacation stay wit...
Proud Bear Inn
Tucked along Town Farm Road in Ludlow, the Proud Bear Inn is a bed and breakfast built on one simple promise: making guests feel at home. It's a relaxed, easygo...
Okemo Mountain Resort
Okemo Mountain Resort anchors Ludlow with year-round slopeside lodging that runs from hotel-style rooms to full condos. Jackson Gore Village holds the Jackson G...
Winterplace on Okemo Mountain
Winterplace puts you slope-side on Okemo Mountain with true ski-in/ski-out condominiums, steps from the Sunburst Six bubble chair. Two- and three-bedroom units ...
Jackson Gore Inn
At the base of Jackson Gore on Okemo Mountain, Jackson Gore Inn keeps you slope-side with the full resort treatment. Heated underground parking leads in from th...
Trojan Horse Lodge
Converted from a century-old carriage barn, the Trojan Horse Lodge is a one-of-a-kind stay just a mile from Okemo's slopes. Part lodge, part living history, it ...
Inside Edge Rentals at Okemo
If you'd rather have a kitchen and room to spread out near Okemo, Inside Edge Rentals at Okemo is a Ludlow-based vacation rental agency with slope-side condos a...
LudlowRentals.com ⭐ Featured
LudlowRentals.com is where Okemo-area vacation homes book direct with their host - Ludlow, the hometown of Okemo Resort. Browse houses, cabins, and condos in Lu...
Main + Mountain Motel
Tucked in the heart of Ludlow, about five minutes from Okemo Mountain Resort, Main + Mountain is a thirteen-room boutique motel done up right — bright, airy roo...
Ludlow Village Inn and Suites
Right on Main Street in Ludlow, about a mile from Okemo, the Ludlow Village Inn and Suites keeps ski-trip lodging simple and friendly. Its seven suites — two- a...
The Governor's Inn
A Victorian country home right on Ludlow's Main Street, The Governor's Inn puts you within walking distance of the village shops and restaurants and just 1.4 mi...
Good Commons
Good Commons in Plymouth is part yoga retreat, part old Vermont farmhouse hospitality. The 4,700-square-foot house — carrying a 150-year tradition of rest and r...
Grafton Inn
In storybook Grafton village, the historic Grafton Inn has been the community's gathering spot for generations — and it's owned by the Windham Foundation, whose...
Echo Lake Inn
Tucked by its namesake lake just four miles from Okemo, the Echo Lake Inn is a classic Vermont country inn with a loyal following. Guests can swim in the season...
Hawk Inn & Mountain Resort
Spread across 1,200 acres in Plymouth, Hawk Inn & Mountain Resort pairs a 50-room four-season inn with luxurious two-, three-, and four-bedroom mountain villas ...
The Inn at Water's Edge
Set between Echo Lake and the Black River just outside Ludlow, The Inn at Water's Edge is a boutique waterfront bed-and-breakfast established in 1999 and fully ...
Combes Family Inn
A 150-year-old farmhouse on a quiet back road off scenic Route 100, Combes Family Inn sits on 50 acres of rolling meadows and woods made for wandering — and cro...
Motel in the Meadow
Motel in the Meadow is a Chester classic built for longer stays — two-night minimums, with preference given to folks settling in for five days or more. Set at 9...
Stone Hearth Inn & Eatery
Stone Hearth Inn & Eatery sits at 698 VT-11 in Chester, a historic inn with its own downstairs eatery and beautiful backyard dining. Guests wake to a cooked-to-...
The Pointe at Castle Hill
On the grounds of Castle Hill Resort near Proctorsville, just a short drive from Okemo Mountain Resort, The Pointe is a comfortable stay with room types that su...
Bethany Birches Camp
Set in the hills of Plymouth, Bethany Birches is a faith-based camp that's been welcoming kids to summer and winter camp for generations — the kind of place whe...
Inn Victoria
An 1859 Victorian on Chester's village green, Inn Victoria is a romantic, family-owned bed and breakfast 20 minutes from Okemo Mountain. Antique-furnished rooms...
Fullerton Inn
On 2.5 acres of gardens in historic Chester, the Fullerton Inn has welcomed travelers since 1885. Its 20 guest rooms — each with a private en-suite bath — are d...
Chester House Inn
The Chester House Inn has stood at 266 Main Street since about 1780, steps from Chester's shops, restaurants and galleries. Inside are seven uniquely decorated ...
Golden Stage Inn
The Golden Stage Inn has welcomed travelers since 1788, when it served as a stagecoach stop in Proctorsville. Today it's an eight-room inn where every guest roo...
Vermont's 1828 Reunion House
Built in 1828, Vermont's 1828 Reunion House is made for gathering. This historic Chester farmhouse pairs an eight-bedroom main house with a separate lodge, givi...
Henry Farm Inn
A 200-year-old farmhouse on the Green Mountain Turnpike in Chester — once the town's first tavern and a stagecoach stop on the road from Boston to Montreal — no...
Cozy Main Street Home - 9 min to Okemo (Airbnb) ⭐ Featured
Cozy Main Street Home is a welcoming whole-home Airbnb rental on Main Street in Cavendish, Vermont, moments from Ludlow and the slopes of Okemo Mountain Resort....
Old Town Farm Inn
A country inn on Route 10 outside Chester, the Old Town Farm Inn sits in the heart of Okemo ski country — and hides one of southern Vermont's most unusual dinin...
Caton Place Campground
Caton Place Campground is a family-owned campground in the foothills of Cavendish with a fine view of Okemo Mountain, open May 15 through October 15. It offers ...
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