6 Bedrooms Plus a Private Hot Tub
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Amazing Ski-In, Ski-Out Airbnbs in Okemo

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6 Bedrooms Plus a Private Hot Tub
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Trailside Condo at Okemo
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Trailside Condo at Okemo

Ludlow | Sleeps 11

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This four-bedroom, three-bathroom condo is just steps from the Sachem Trail. You can step out of the second floor, put on your skis, and then head to the lift. It’s easy to ski home for lunch, and the kitchen is fully stocked with utensils for easy meal prep.


Trailside Condo at Okemo
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Trailside Condo at Okemo: More

This three-floor property includes an entrance on the lower level with a den and fireplace. You’ll find a small sauna on the first level, plus a second-floor open layout kitchen, and living room with fireplace. The third floor has the master suite. Glass sliders provide picturesque mountain views. 


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2-Bedroom Winterplace Condo
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2-Bedroom Winterplace Condo

Ludlow | Sleeps 6

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This condo is located in the Winterplace development, right by the Lift Line ski trail (the lift is right behind the building). There’s even a beginner-level trail from Winterplace down to the base lodge, so this rental is ideal for skiers of all levels.


2-Bedroom Winterplace Condo
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2-Bedroom Winterplace Condo: More

In addition to the two bedrooms and two bathrooms, this condo features a balcony space and a living room with a sleeper sofa. The Winterplace development offers additional amenities including hot tubs, and an indoor pool during the winter. In the summer, you can use the tennis courts and basketball court.

Updated 2-Bedroom in Okemo Trailside
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Updated 2-Bedroom in Okemo Trailside

Ludlow | Sleeps 6

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This two-bedroom, two-bathroom condo is located in the Trailside community, just 50 yards from the Sachem trail. Since the Sachem trail is beginner-rated, the condo is a perfect stay for skiers of any ability. The living room and fireplace make for a cozy spot to relax after a day on the slopes.


Updated 2-Bedroom in Okemo Trailside
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Updated 2-Bedroom in Okemo Trailside: More

During your stay, you’ll enjoy free high-speed Wi-Fi throughout the property. A full kitchen is ideal for meal preparation, and the unit also includes a washer and dryer so you can wash your ski gear. There’s also a deck off of the living room, so you can take in the views.

Winterplace 2-Bedroom Condo
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Winterplace 2-Bedroom Condo

Ludlow | Sleeps 6

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Situated within the Winterplace community, this condo is within walking distance to the ski trail. It’s also just across the parking lot from the pool house, so you can easily get to the pool and hot tubs. Two chair lifts come up from the base lodge and let out by Winterplace, giving you great access to the mountain.


Winterplace 2-Bedroom Condo
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Winterplace 2-Bedroom Condo: More

This two-bedroom, two-bath condo features a living room with a sofa and fireplace, as well as a balcony. The kitchen is equipped with a fridge, coffee maker, microwave, dishwasher, and toaster, and is stocked with dishes and utensils. You’ll also enjoy free Wi-Fi during your stay.

Cozy Condo Trailside on Sachem Trail
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Cozy Condo Trailside on Sachem Trail

Ludlow | Sleeps 11

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This four-bedroom, 2.5-bath condo is situated slopeside, just steps from the Sachem trail. There’s no need to cross parking lots, so it’s easy to ski home for lunch or to bypass shuttles at the end of the day.  Sleds for the kids are included for more laid-back winter fun.


Cozy Condo Trailside on Sachem Trail
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Cozy Condo Trailside on Sachem Trail: More

In addition to the bedrooms, this condo also features a loft. The living room and fireplace are the perfect place to relax, while kids can entertain themselves with the air-hockey table or board games. A breakfast bar off the kitchen ensures plenty of seating, and the kitchen is fully stocked.

4-Bedroom Townhome in the Trailside Community
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4-Bedroom Townhome in the Trailside Community

Ludlow | Sleeps 10

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This condo is located 400 yards from the Sachem trail, but there’s also a shuttle that you can take for a quick trip to the ski trail. Because the Sachem trail is beginner-rated, this rental is ideal for the whole family and skiers of all levels. A mud room in the main entry level is the perfect place to put on your ski gear.


4-Bedroom Townhome in the Trailside Community
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4-Bedroom Townhome in the Trailside Community: More

This four-bedroom, 2.5-bath townhome features two levels with plenty of room for your whole family or group of friends, including a sleeper sofa and a laundry room. It comes equipped with free Wi-Fi and a Wii gaming system for entertainment when you’re not on the slopes.

1-Bedroom Condo with a Walk to the Lifts
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1-Bedroom Condo with a Walk to the Lifts

Ludlow | Sleeps 4
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This second-floor condo is situated right at the base of Okemo Mountain, and the lift is just steps away. It features beautiful views of the Clock Tower base lodge. You’ll be right near the action and enjoy convenient access to the base area and ski school. There’s even a heated ski locker right outside your door.


1-Bedroom Condo with a Walk to the Lifts
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1-Bedroom Condo with a Walk to the Lifts: More

This one-bedroom, one-bathroom condo features a balcony with a view of the lifts. You’ll enjoy wireless high-speed internet access, and there’s a sleep sofa in the living room for extra space. There’s also a coin-operated washer and dryer in the building.

5-Bedroom Chalet
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5-Bedroom Chalet

Ludlow | Sleeps 12 

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This single family home is just 200 yards from the Sachem trail. Its multi-level design and five bedrooms provide plenty of space, and there’s a private hot tub that’s ideal for relaxing after a day outside. The cozy living room features a fireplace, perfect for quiet afternoons or evenings, and there are two full bathrooms.


5-Bedroom Chalet
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5-Bedroom Chalet: More

This chalet features a kitchen that comes complete with all of the essentials, like a microwave, fridge, dishwasher, and coffee maker. There’s a TV and DVD player to keep your family entertained, and your stay also includes free Wi-Fi.

4-Bedroom Trailside Townhome with Private Hot Tub
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4-Bedroom Trailside Townhome with Private Hot Tub

Ludlow | Sleeps 12

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This condo is located in the Trailside community and is just 20 yards to the Sachem trail. It’s an end unit for increased privacy, and there’s a hot tub on the deck when you’re ready to unwind after a day on the slopes. The mud room on the entry level is the perfect place to put on your ski gear. 


4-Bedroom Trailside Townhome with Private Hot Tub
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4-Bedroom Trailside Townhome with Private Hot Tub: More

This four-bedroom condo features two full bathrooms and one half-bath. The multi-level design gives your whole family space to relax. The living room features a fireplace and is a great place to relax. There’s also a TV with a DVD player, a washer and dryer, and free Wi-Fi.

Slopeside Okemo Mountain Home
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Slopeside Okemo Mountain Home

Ludlow | Sleeps 15

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This five-bedroom, five-bathroom ski home is located right at the base of Okemo Mountain. The mudroom entry is equipped with a huge boot and glove dryer, plus tons of places to hang your clothes, as well as a washer and dryer. The sunny deck offers beautiful mountain views.


Slopeside Okemo Mountain Home
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Slopeside Okemo Mountain Home: More

The two master suites have jetted tubs, or you can relax in the first-floor sauna or the hot tub on the deck after a day skiing. The living and dining area features beautiful flooring, and the floor-to-ceiling fireplace makes for a stunning addition. There are plenty of closets, including walk-ins in the master bedrooms for storage.

6 Bedrooms Plus a Private Hot Tub
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6 Bedrooms Plus a Private Hot Tub

Ludlow | Sleeps 22

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Located right on the Sachem ski trail, this home is ideal for large ski groups or families with six bedrooms, a den, plus a loft. The home also features a private hot tub that’s the perfect way to unwind after a day of skiing.


6 Bedrooms Plus a Private Hot Tub
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6 Bedrooms Plus a Private Hot Tub: More

This home features a large dining room and kitchen, as well as a living room with a fireplace. The loft area on the fourth level features two twin beds for additional space. The home even has an attached apartment with a full kitchen, living room, and a washer and dryer.


Large Luxury 5-Bedroom Home
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Large Luxury 5-Bedroom Home

Ludlow | Sleeps 16

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This spacious home is situated just 150 yards from the Sachem trail, perfect for larger groups or families that love to ski. The multi-level arrangement gives you plenty of room to spread out, and the wood burning fireplace in the living room makes for an ideal after-ski gathering spot.


Large Luxury 5-Bedroom Home
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Large Luxury 5-Bedroom Home: More

When you’re not on the slopes, you’ll find plenty of entertainment in the recreation room, complete with a foosball table and flatscreen TV. The home features five bedrooms and seven bathrooms, and your stay includes free Wi-Fi. There’s also a washer and dryer.

Private Classic Vermont Ski Chalet
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Private Classic Vermont Ski Chalet

Ludlow | Sleeps 13

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This five-bedroom, two-bathroom chalet is situated on a wooded lot that’s just 100 yards from the Sunshine chairlift and Suncatcher trail. Take a short drive down the mountain and you’ll find Ludlow’s restaurants and shops. This chalet is close to a babbling brook and features an outdoor fire pit. 


Private Classic Vermont Ski Chalet
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Private Classic Vermont Ski Chalet: More

Indoors, you’ll find a central sitting room with a fireplace, TV, and DVD player. There's a mudroom for all of your gear, and a fully renovated kitchen with stainless-steel appliances. The chalet is stocked with DVDs, books, games, and puzzles.

5-Bedroom with Hot Tub on the Sachem Trail
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5-Bedroom with Hot Tub on the Sachem Trail

Ludlow | Sleeps 12 

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Located directly on the Sachem trail, this single family home gives you convenient access to the slopes. Ski home for lunch or at the end of the day, then relax in the private hot tub that overlooks the trail. The deck offers beautiful nature views.


5-Bedroom with Hot Tub on the Sachem Trail
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5-Bedroom with Hot Tub on the Sachem Trail: More

This home features 4.5 baths and a multi-level design. Linens are provided, and your stay includes free Wi-Fi. The kitchen is equipped with a fridge, microwave, coffee maker, dishwasher, and toaster. There’s even a washer and dryer for your ski gear. 

Spacious 4-Bedroom High on the Mountain
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Spacious 4-Bedroom High on the Mountain

Ludlow | Sleeps 8

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Situated high on Okemo Mountain, this four-bedroom, two-bathroom home is just steps from the trails. There’s no need to ski to the base, and you can easily ski to the Sunburst 6 Bubble, Sachem, or South Ridge quad lifts. This location makes it super easy to ski home for lunch or a change of clothes. 


Spacious 4-Bedroom High on the Mountain
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Spacious 4-Bedroom High on the Mountain: More

At the end of the day, relax in front of the fireplace; your stay includes all the free firewood you want. The kitchen is stocked with utensils and supplies, and includes a dishwasher, toaster, oven, grill, and more. You can even enjoy the communal pool and spa in the recreational building.

Newly Built 3-Bedroom with a Private Hot Tub
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Newly Built 3-Bedroom with a Private Hot Tub

Ludlow | Sleeps 12

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Located just steps from the Base Lodge, this three-bedroom, three-bathroom single family home is also within walking distance of the F-10 Magic Carpet at the Clock Tower Base Lodge. There’s plenty of space to relax, and the home includes a private hot tub that’s perfect after a day on the slopes.


Newly Built 3-Bedroom with a Private Hot Tub
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Newly Built 3-Bedroom with a Private Hot Tub: More

The living room features a gas fireplace, and there’s also a family room with an air hockey table. The home features laundry facilities and a mud room for your ski gear, and linens and wireless internet are provided.

Kettle Brook 2-Bedroom Condo
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Kettle Brook 2-Bedroom Condo

Ludlow | Sleeps 6

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This two-story condo is situated within the Kettle Brook community, with easy access to the Kettle Brook and Bull Run trails. Its wooded setting is picturesque, and offers beautiful views.


Kettle Brook 2-Bedroom Condo
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Kettle Brook 2-Bedroom Condo: More

With two bedrooms and two bathrooms, this condo is ideal for two couples. There’s also a queen sleep sofa in the living room for additional space. Amenities include television, linens, dishes and utensils, free Wi-Fi, and a washer and dryer.

Highest Property on Okemo with Stunning Views
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Highest Property on Okemo with Stunning Views

Ludlow | Sleeps 10

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This four-bedroom, 2.5-bath townhome is in the Trailside community, close to the Sachem trail. The wrap-around deck offers stunning mountain views of this beautiful location. Since the Sachem trail is beginner-friendly, this is an ideal rental for families or skiers of any experience level.


Highest Property on Okemo with Stunning Views
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Highest Property on Okemo with Stunning Views: More

After a day of skiing, relax by the fireplace in the living room. There’s a TV and DVD player for entertainment. The townhome features a washing machine and dryer for your gear, and the kitchen is equipped with a fridge, microwave, coffee maker, and toaster.

1-Bedroom Condo with Modern Decor
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1-Bedroom Condo with Modern Decor

Ludlow | Sleeps 4

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This newly renovated one-bath condo is just steps from the lifts. The private balcony provides beautiful views, perfect for enjoying a coffee before heading out on the slopes. Located on the third floor, this vacation rental includes free high-speed Wi-Fi.


1-Bedroom Condo with Modern Decor
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1-Bedroom Condo with Modern Decor: More

The fully equipped kitchen features updated appliances and plenty of cookware for easy and convenient meal prep. The living area features a fireplace and a flatscreen TV, making it the perfect place to relax after a long day.

3-Bedroom Winterplace Condo
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3-Bedroom Winterplace Condo

Ludlow | Sleeps 8

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This three-bedroom, two-bathroom condo is situated for easy access to all that Okemo has to offer. It’s a 5-minute walk to Okemo Mountain Resort, or a 7-minute drive to Dorsey Park. The patio provides a picturesque view, and the property also features an indoor pool.


3-Bedroom Winterplace Condo
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3-Bedroom Winterplace Condo: More

There’s also plenty to do inside the condo. A fridge and coffee maker offer convenience, and there’s a washer and dryer you can use for your ski gear. A fireplace makes the living room a cozy spot, while there’s also free Wi-Fi, TV, video games, and a DVD player to keep the whole family entertained.