Ski-in/Ski-out vacation 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!

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 !

Elegant Alpine Condo

Newly renovated 1-bedroom Whiffletree condo with an upscale alpine feel—just minutes from the slopes, access road, and snow tubing. Fully stocked with essentials and includes a ski locker for your gear. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). 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. Killington Reg #007718

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.

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking

Our bright and cozy 1-bedroom condo in Building 3 at Mountain Green Resort is the perfect home base for your Killington getaway. Reserved parking spot in the garage. Walk to Snowshed Base Lodge or hop on the winter shuttle that runs every 15 minutes. Enjoy a renovated kitchen, dedicated Wi-Fi, and smart TVs for easy streaming. Resort amenities include an indoor pool, hot tub, sauna, and gym year-round, plus an outdoor pool from Memorial Day through mid-September.

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

Mt Snow Ski In/Out at Seasons

Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. Free parking. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.

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.

Vermont Getaway Apartment

A 2 bedroom apartment attached to our home, close to Stratton, Bromley, Magic, Okemo & Mt Snow Skiing, hiking, fishing, golfing, tennis, outlet shopping and fine dining all close by. Manchester a short drive. Hot tub available from 8am-8pm. Level 2 EV charger available for a $10 cash fee (and give us advance notice if possible so we can open the garage for you).