Ski-in/Ski-out holiday rentals in Londonderry

Lovers Honey Pond Treehouse with hot tub & sauna

Guest Favorite VERY romantic abode…The Honey Pond Treehouse is made for you and yours! It’s constructed of all natural materials, has breathtaking views, and is outfitted with absolutely everything you need! Lifted high over a stocked trout pond way up in the birch trees…Enjoy private hot tubbing, sauna time, swimming & hammock time. Skylight was designed for stargazing in bed!! Just minutes to the slopes or enjoy our own groomed trails for Xcountry & snowshoes & nature walks!! High speed WiFi 🐣

Freemans Grove Benevolent Society Walk to MoCA

Welcome to the Freeman's Grove Benevolent Society! Artist's apartment/gallery with kitchen, bath, one bedroom, and a sleeping nook. It is an open floor plan, for heating purposes there are curtains (no doors) on the bedroom and sleeping nook. Sleeps 4 people comfortably. The walk from MASS MoCA to the house is flat except the last block which is STEEP! The apartment is a flight and a half off the street, so be prepared for some stairs. A truly unique apartment and cabinet of curiosities. #fgbs

Summit View Ski and Golf Retreat w/hot tub & Sauna

Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

Cozy Mountain Condo

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! Sleeps up to 4 with a king bed and queen pullout sofa. Baby Pack & Play crib, mattress and sheets available upon request for $50 per stay. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Killington Reg #004858

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

PLEASE NOTE: No Saturday arrivals or departures, no pets, no parties Recommended local activities & floor plans of our home can be found on our OkemoHouse site Our "Trailside Chalet" is ON OKEMO MOUNTAIN, a 200 yard walk downhill from the Sunshine Chairlift & Suncatcher ski trail on Okemo's Southface (open end if Dec - late Mar). This Classic Vermont Ski Chalet features 5 bedrooms, sleeps 12, and is on a private wooded lot overlooking a babbling brook with seasonal fire-pit & charcoal grill.

Jack S'Bearo - Slopes, Fireplace, Pool.

Ahoy, ski enthusiasts! "Jack S'Bearo" - a renovated 1-bed, 1-bath on Pico Mountain, VT, offers an exhilarating ski experience steps from the lift and a shuttle to Killington Resort. The new kitchen, wood-burning fireplace, and balcony make it a haven for relaxation. This ski on/ski off treasure boasts a cool design for easy access to the slopes. Grab your gear from the ski locker, step outside, and set sail to the lifts. Make "Jack S'Bearo" your pirate's cove, where adventure meets comfort!

Suite 23 - Spacious Sunny 2-BR with Mountain view

Our happy place is a 5 minute walk to Berkshire East/Thunder Mountain . An 8 minute walk to the Deerfield River for guided fishing tours with Hilltown Anglers, kayaks, ,whitewater rafting. 10 minute walk to town and shuttle for tubing. A 5 minute drive to local wedding venues. We provide a full kitchen with all cooking essentials, a private picnic area with charcoal grill (charcoal provided). We reside at the single family home on property and we’re excited to share our Suite 23 !

Midcentury Hillside Retreat - Summer Paradise

Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.

The Grateful Barn

THE GRATEFUL BARN IS BACK ! Renovated 1800's Vermont barn. Located on a National Forest Rd. & land locked by the entire Green National Forest. The Grateful Barn is a cozy converted barn located next to a seasonal country home. The Barn offers a private bedroom with a queen sized bed, 2 single beds in a loft area & a pull out double bed in living room. This remote VT location is just a few steps from the Long Trail …7 minute drive to Bromley & 20 minutes to Stratton or Magic MT.

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Yurt In The Woods - Come to the Yurt.

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.