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Holiday houses in Ludlow

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Top-rated holiday rentals in Ludlow

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Tiny home in Chester
4.98 out of 5 average rating, 135 reviews

Tiny A-Frame Rest House in Woods near Mountains

Newly built A-Frame getaway cabin built in the middle of the woods of Vermont. Unplug from it all at this special space surrounded by nature. Enjoy doing yoga and relaxing on the deck, remote working with fiber optic wifi, utilizing the fire pit to roast smores, or taking a walk around the walking paths on the property! There are also nearby hikes, swimming spots, skiing destinations, and drinking/eating spots! We are 35-40 minutes from Stratton, Mount Snow, Bromley, Okemo, and Magic Mountain!

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Guest favourite
The cabin entrance is framed by freshly fallen snow, with wooden siding that blends into the winter landscape. A lantern on the left provides a soft glow, illuminating the path. Tranquil trees surround the area, enhancing the serene atmosphere.
Cabin in Plymouth
4.99 out of 5 average rating, 131 reviews

~The ClubHaus~

Appreciate life at our peaceful home away from home in the Vermont Woods... Located a short drive from Killington and Okemo ski mountains, The ClubHaus is the perfect spot to unwind after enjoying four season New England activities. Breweries and great food are nearby in Woodstock, Manchester, and Dorset. Huge fireplace, hot tub, comfortable beds, and lots of thoughtful touches provided to welcome you to the ClubHaus family. Wifi, Netflix, and Disney+ included, no cable. @clubhausvt on IG

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Top Guest favourite
Home in Ludlow
4.97 out of 5 average rating, 181 reviews

Ski Chalet with Hot Tub on Okemo Mountain

Newly renovated in fall 2023, this 3-level, 1700+ sq. ft. ski chalet is just a 4 min drive to Okemo Mountain Resort and town, with Jackson Gore only 6 min away. Floor-to-ceiling windows showcase stunning 180-degree views of the wooded backyard, creating a peaceful mountain retreat. Cozy up by the fireplace or soak in the Jacuzzi hot tub for ultimate relaxation. Whether you're here for skiing, hiking, or a quiet escape, this private oasis offers the perfect blend of comfort and convenience.

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Top Guest favourite
Adirondack chairs and a small side table are positioned on a spacious deck, offering an unobstructed view of Okemo resort. The winter landscape features snow-covered ground, complemented by a clear blue sky and distant mountain views.
Home in Ludlow
4.99 out of 5 average rating, 139 reviews

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

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Top Guest favourite
Cabin in Poultney
4.94 out of 5 average rating, 400 reviews

Waterfront Vermont Lake House w/ Panoramic Sauna

Waterfront on Lake St. Catherine, with almost 100ft of private lake frontage and a view that's hard to beat. Watch the sunrise from the deck or from inside our new panoramic barrel sauna. Explore the lake by kayak or canoe — both included for guests. Keep an eye out for both bald eagles and loons. There's also a fire pit for evening s'mores — firewood included as well. Great for families — we've got a crib, a bunk room for the kids, and a bookshelf of board games for those rainy days.

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Top Guest favourite
Tiny home in Ludlow
4.95 out of 5 average rating, 109 reviews

Alpine Reflection + Hot Tub

Escape to this luxury glass tiny home perched at 1,500 feet in elevation in Ludlow, Vermont—architect-designed and built in Estonia with stunning views of Okemo Mountain. Tucked away in a private forest setting, this one-of-a-kind retreat features a hot tub, fire pit, outdoor shower under the trees, radiant heated floors, and floor-to-ceiling windows that immerse you in nature. Designed for quiet luxury relaxation and unforgettable mornings, it’s the perfect escape every season

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Top Guest favourite
A stone patio is illuminated by string lights, featuring a fire pit surrounded by three adirondack chairs in red, blue, and white. Lush greenery is visible in the background, creating a serene outdoor gathering space.
Apartment in Ludlow
4.96 out of 5 average rating, 130 reviews

Peaceful Ludlow base for exploring Okemo valley

Newly renovated, clean 1 BR apt. in historic house 2 blocks to town, 5 minute drive to Okemo, Buttermilk Falls, and 2 minute walk to the Ludlow Farmers Market. Enjoy complimentary coffee and local maple syrup while overlooking the town of Ludlow. Make yourself at home with a full kitchen/bath, wall-mounted flat screen TV, king bed, and comfortable futon. Free EV charging available. Kayaking, hiking, and golfing close by. We are dedicated to ensuring a top-notch experience!

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Guest favourite
The modern timber frame cabin features a covered porch with wooden beams, providing a welcoming entry. Large windows offer views of the surrounding forest, while a landscaped path leads to the entrance, framed by lush greenery and natural stone steps.
Cabin in Ludlow
4.95 out of 5 average rating, 110 reviews

Modern Okemo Smart Cabin - As Seen On DIY Channel

This is a brand new modern timber frame smart cabin in Ludlow (~5 min from Okemo). The house was recently featured on DIY / Discovery’s acclaimed TV show, Building Off The Grid. Warm up after a day of skiing or riding with heated floors and a walk-in shower. Charge up your electric vehicle in the private garage. Directly access the VAST snowmobile trail from the backyard or sit back on the porch and soak up the views. Message host about renting for next winter season!

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Guest favourite
An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.
Cabin in Mount Holly
4.88 out of 5 average rating, 170 reviews

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

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Guest favourite
The spacious living area features warm wood paneling and a polished floor. A dining area with a wooden table is elevated, while a cozy seating arrangement with colorful cushions is nestled on the ground. Soft lighting from overhead fixtures creates a welcoming ambiance.
Loft in Ludlow
4.95 out of 5 average rating, 902 reviews

Spacious Renovated Barn Apt on 100 acres!

Our unique hideaway is only two miles from many restaurants and cute shops in Ludlow, and we are 1 mile from the gorgeous Buttermilk Falls and Jackson Gore at Okemo Mountain Resort where you can enjoy mountain biking, a ropes course or skiing and riding! Enjoy 100 acres of hiking or snowshoeing right outside your door. There is nice fire fire pit, hot tub and outdoor seating. Perfect location for the outdoor enthusiast or a relaxing weekend in cool VT air!

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Top Guest favourite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 777 reviews

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

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Top Guest favourite
A cozy living room features warm wooden paneling and a plush sofa facing a mounted flat-screen television. A circular coffee table sits in the center, complemented by a floor lamp and a side chair. A fireplace adds a comforting touch, creating a welcoming space.
Condo in Ludlow
4.95 out of 5 average rating, 193 reviews

Lovely 1-Bedroom condo with indoor fireplace!

This cozy condo is exactly what a close group of 4-5 people need for a wonderful ski experience. Located centrally in the beautiful town of Ludlow this location is close to everything you could want. It sits on the bus route for Okemo Mountain, and is walkable to groceries, restaurants and bars. "Eight Oh Brew" tap house is located on the base floor of the building. This location has free onsite parking, free firewood and coin laundry machines.

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Popular amenities for Ludlow holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Ludlow's top sights

Okemo Mountain Resort

530 locals recommend

Camp Plymouth State Park

102 locals recommend

Lake Rescue

22 locals recommend

Fox Run Golf Club

78 locals recommend

Okemo State Forest

17 locals recommend

Lake Ninevah

10 locals recommend

Other great holiday rentals in Ludlow

Guest favourite
A modern two-story cabin, featuring a rich red exterior, is nestled among autumn trees. Large windows allow natural light to fill the interior. A seating area with dark chairs is positioned around a fire pit, accentuating the outdoor space surrounded by colorful fall foliage.
Cabin in Cavendish
4.96 out of 5 average rating, 114 reviews

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

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Top Guest favourite
Cabin in Shaftsbury
4.99 out of 5 average rating, 327 reviews

The Hygge Loft- mid-mod cabin on 70 acres w/HotTub

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Top Guest favourite
Shipping container in Ludlow
5.0 out of 5 average rating, 11 reviews

Luxury Container Home with Sauna & Heated Pool

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Top Guest favourite
An airy living space is showcased, featuring high ceilings with natural wood beams. Large windows provide ample daylight and views of the surrounding trees. A cozy seating arrangement is placed adjacent to a dining area, while a large area rug adds warmth to the wooden floor.
Home in Ludlow
5.0 out of 5 average rating, 42 reviews

The Evergreen Chal-A

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Top Guest favourite
Treehouse in Jamaica
5.0 out of 5 average rating, 9 reviews

The Treehouse at Frog Pond Farm

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Superhost
A spacious dining area features a round marble table surrounded by yellow chairs. A cozy living space is visible, showcasing wood furniture and decorative accents. Large windows allow natural light to illuminate the room, while a spiral staircase leads to the upper level.
Chalet in Ludlow
4.81 out of 5 average rating, 111 reviews

Okemo Mountain-Newly Renovated w AC, hottub, WiFi

LocationFamilyAir conditioning

Guest favourite
An inviting living area features a soft couch draped with a textured blanket, complemented by a wooden coffee table and a dining table. Natural light floods in through a large window framing a view of the serene lake and surrounding greenery. A lamp stands quietly in the corner.
Cottage in Mount Holly
4.95 out of 5 average rating, 20 reviews

Idlewild Cottage on Star Lake Near Okemo

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Top Guest favourite
Home in Ludlow
5.0 out of 5 average rating, 14 reviews

Ludlow Retreat-Hot Tub, Sauna & Game Room

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Frequently Asked Questions

  • What are the best places to stay in Ludlow?

    Ludlow has vacation rentals near Okemo Mountain, historic homes in the village, and cozy cabins nestled in the woods. Many accommodations provide easy access to outdoor activities and local dining.

  • What are the best things to do in Ludlow with kids?

    Kids often enjoy the adventure zones and skiing at Okemo Mountain Resort, or exploring playgrounds and easy walking trails nearby. Warmer months bring opportunities for picnicking and water activities around the area.

  • What are some of the best things to do in Ludlow?

    Explore Okemo Mountain's activities, visit local art galleries, and sample Vermont maple products. In winter, skiing and snowboarding are popular, while summer invites hiking and lake adventures.

  • How is the weather in Ludlow?

    Ludlow has cold, snowy winters with temperatures ranging from 13–32°F (-11–0°C), and mild to warm summers between 57–81°F (14–27°C). Spring and fall bring variable weather and colorful scenery, so layering is usually suggested.

  • When is the best time to visit Ludlow?

    Winter is often recommended for snow sports, while late spring through early fall attracts visitors with moderate temperatures and colorful foliage. Summer has local festivals and outdoor recreation at lakes and trails.

  • What are the best places to visit in Ludlow?

    Ludlow has the Okemo Mountain Resort, known for year-round activities, and the Ludlow Village Historic District with classic New England architecture. Visitors also explore craft shops, breweries, and nearby lakes and parks.

  • What are some hiking trails in Ludlow?

    Ludlow has scenic trails winding through forests and up gentle slopes, with some accessing views of the surrounding Green Mountains. The Okemo Mountain area is frequently suggested for hiking routes, providing options for beginners and experienced hikers alike.

  • What are some family activities we can do in Ludlow?

    Families enjoy all-ages skiing and snowboarding at Okemo Mountain Resort, hiking local trails, and visiting lakes for swimming or kayaking in warmer months. The village also has ice cream shops and playgrounds.

  • What are some of the best day trip ideas from Ludlow?

    Guests often visit nearby state parks for hiking and swimming, explore charming mountain towns known for arts and local shops, or tour historic villages. The region is also famous for scenic drives, particularly during fall foliage season.

  • Are there any pet friendly accommodations available in Ludlow?

    Many vacation rentals and lodges in Ludlow welcome pets. Trails and parks around Okemo Mountain and the village provide outdoor spaces to explore with companion animals.

  • What are some local tips for visiting Ludlow?

    Layered clothing is useful, as temperatures can shift quickly. Many visitors take advantage of the local food scene and outdoor markets, and booking accommodations early is often suggested during peak seasons.

  • What is Ludlow known for?

    Ludlow is known for the Okemo Mountain Resort, seasonal outdoor activities, and its historic village charm. The area has a tradition of welcoming visitors year-round for skiing, hiking, and exploring local culture.

  • What are the best hidden gems to explore in Ludlow?

    Travelers often seek out small art galleries, local farm stands with maple products, and secluded forest trails near the village. Quiet lakes and lesser-known park areas around Ludlow are frequented by those looking for peaceful surroundings.

  • What are the best foods to try in Ludlow?

    Travelers often enjoy seasonal Vermont produce, freshly baked goods, and regional specialties like maple syrup and sharp cheddar cheese. Local eateries may have farm-to-table dishes and classic comfort foods inspired by New England traditions.

  • What should I bring for a trip to Ludlow?

    It is helpful to pack layered clothing, waterproof outerwear, and comfortable shoes for exploring trails. In winter, warm gear and snow boots are often needed, while summer visitors may want swimwear for lakes and sunscreen for outdoor activities.

  • What is the nightlife in Ludlow like?

    Nightlife in Ludlow leans toward neighborly pubs, cozy taverns, and relaxed venues with live music, especially during ski season. Many spots serve Vermont craft beer and comfort food in welcoming settings.

  • What are the most popular events or festivals in Ludlow?

    Ludlow celebrates winter with ski season festivities at Okemo Mountain Resort and often hosts local fairs, summer farmers' markets, and autumn harvest events. Seasonal arts and music gatherings around the village are also frequently suggested.

  • Are there family friendly vacation rentals in Ludlow?

    Ludlow has many family-friendly vacation rentals, including cozy cabins and larger homes near Okemo Mountain or in the village. These stays often feature kitchens, living areas, and access to outdoor space for group activities.

Destinations to explore