Ski-in/Ski-out vacation rentals in Ludlow

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Top-rated ski-in/ski-out rentals in Ludlow

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Guest favorite

Condo in Killington

4.9 out of 5 average rating, 119 reviews

Cozy & Convenient Ski Home Condo

Ski Home to Trail Creek Close to the mountain This updated 1-level, 1 bedroom, 1 bath, condo is walking distance to Snowshed Base where you can access skiing, biking and the "fun" center. Ski home to your door from Snowshed Slope trail. Steps to the amenities building that houses the pool, hot tub, sauna & exercise area. Wood-burning fireplace, free firewood, in-unit laundry. The view outside your living area is of bucolic woods and a small stream. Killington will not run the shuttle mid-week.

Aug 23 – 30

G$35,523 GYD per night

Guest favorite

Condo in Ludlow

4.95 out of 5 average rating, 110 reviews

Slopeside condo at the base of Okemo-steps to lift

Welcome to Okemo MTN Lodge! Our clean slopeside condo at the base of Okemo makes things super convenient. This 1 bdr condo on the 3rd fl (no elevator) has 1 queen & 1 bunk. Steps to lift. Reserved parking for 1 car. This unit is our spot—it’s not an investment property. We use rental income to help cover costs for my 2 kids who travel and compete as snowboarders. Watch the crowds from our deck. Condo is best for4 ppl. max. This is an older building. Brand new floors, paint, and bathroom. 🏂⛷

Sep 30 – Oct 7

G$59,844 GYD per night

Superhost

Condo in Ludlow

4.8 out of 5 average rating, 148 reviews

Enjoy a Ski-On/Ski-Off Okemo Ski Getaway

Perched on Okemo mountain, step to the trails and start your day with no need to ski to the base. You will be on the best ski/on-ski/off location directly to Sunburst 6 Bubble, Sachem or South Ridge Quads & boarding park lifts; while having everything you might need for a cosy and convenient family stay. That includes a fully-equipped kitchen and a living room with games for your entertainment, a private balcony, laundry facilities and shared resort-style amenities at Winterplace with pool.

Apr 6 – 13

G$88,852 GYD per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 122 reviews

All Season Lovely and Zen Okemo Mt Lodge Condo

Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the wood-burning fireplace*, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

May 1 – 8

G$19,489 GYD per night

Guest favorite

Condo in Killington

4.83 out of 5 average rating, 120 reviews

Charming 3 Bedroom 2 Bath Ski Home/Off

Looking to access everything Killington has to offer within 2 minutes? This is your spot! Ski off access, right on the bus route, a 2 minute drive to the mountain. Whether you're skiing, hiking, biking, shopping, or eating and drinking, you will love the convenient location to everything that is Killington. This three bedroom, two bathroom condo was just updated with a fresh look and is ready for you to come relax on the sofa in front of the gas fireplace after a long day with nature.

Sep 10 – 17

G$43,033 GYD per night

Guest favorite

Condo in Stratton

4.94 out of 5 average rating, 138 reviews

Updated Ski in/Ski out Stratton Condo!

Enjoy our cozy ski-in ski -out condo in the Ober Tal complex at Stratton. This newly renovated condo offers a warm, welcoming stay with modern farm house charm! Located just above the base of the mountain, our condo is a stones throw from the nearest lift ( 200 ft) and a ski lovers dream. Unwind after a long day of skiing/snowboarding or take convenient 5 minute stroll to the Village for a bite to eat or some shopping. *Mountain biking & concerts offered in the summer season.*

Jun 6 – 13

G$27,219 GYD per night

Guest favorite

Condo in Killington

4.96 out of 5 average rating, 103 reviews

CozyCub- Ski Off, Shuttle On, Fireplace, Renovated

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer, settle in by the gas fireplace, or head out to explore.

Nov 25 – Dec 2

G$84,010 GYD per night

Guest favorite

Tiny home in Hartland

4.95 out of 5 average rating, 144 reviews

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.

Sep 21 – 28

G$19,308 GYD per night

Guest favorite

Home in Peru

4.92 out of 5 average rating, 139 reviews

Beautiful Bromley/Manchester VT Retreat w/hot tub

Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Comfortably accommodates 12 people. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

May 9 – 16

G$70,415 GYD per night

Guest favorite

Bungalow in Williamstown

4.89 out of 5 average rating, 202 reviews

Hollywood Bungalow in the Berkshires

Cool Cozy Rustic Country Bungalow with Screening Room on filmmakers/artists' enclave that's well-located in clean and beautiful Williamstown, near incredible Hiking Trails, Farms, Skiing, MASS MoCA, Clark Art Institute, Williams College, with Pool access, Cable & Smart TV, Porch and Patio, Grill, Fire Pit, Piano Bar Outbuilding with stereo & its own WIFI, First Floor Bathroom with Jacuzzi Bathtub, Laundry, fast WIFI, and lots of outlets in a quiet area on a quiet street.

Apr 7 – 14

G$48,894 GYD per night

Guest favorite

Condo in Killington

4.81 out of 5 average rating, 140 reviews

1BR Modern Condo @ Whiffletree Ground Fl Walkout

PRIME BASE AREA LOCATION THE HOME → King Beautyrest mattress → Coffee/Tea/Cocoa Bar → Nintendo Wii + Games → Fully Equipped & Stainless Kitchen → Fast Wifi SKI IN / SHUTTLE OUT (2022: Winter Only; Weekends only) → Shuttle to Snowshed/K1 → Ski home on a gorgeous quiet ski home trail OFF SEASON → World Class hiking & biking on Killington Mountain OFF THE MOUNTAIN → Breweries → Antique Malls → Golf Courses → Quechee Gorge → Disk Golf → Llamas Petting

Sep 22 – 29

G$33,692 GYD per night

Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 123 reviews

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.

May 14 – 21

G$20,437 GYD per night