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Condo holiday rentals in Windsor County

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Top-rated condo rentals in Windsor County

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Superhost
A cozy living area is presented, featuring a blue sectional sofa complemented by decorative pillows. A wooden coffee table sits in front, with remote controls arranged on top. Vintage skis are mounted on the wall, adding a rustic charm, while lamps provide soft lighting.
Condo in Killington
4.84 out of 5 average rating, 274 reviews

Comfy ski in/out studio at base of Pico-Killington

Studio at the base of Pico with a balcony. Free shuttle service from my place to Killington, which is 10 minutes away.Brand new sofa bed with a pillow top. Room divider. Lots of TV channels with Xfinity. Luggage cart and elevator for easy access. Fast Wi-Fi. Free ski locker with one key for each guest. There is a laundry room with coin operated machines. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for one day. No daily cleaning service. No parties. Free parking

Top Guest favourite
A spacious living room features a comfortable sectional sofa facing a propane fireplace. A mounted TV is positioned above the hearth. Natural light enters through sliding glass doors leading to a private porch, surrounded by lush greenery.
Condo in Mendon
4.94 out of 5 average rating, 117 reviews

Hotel Chic - Home Comfort -Ski Easy.

HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS ❄️Killington - 15 minutes ❄️Pico - 5 minutes ❄️WIFI❄️QUIET❄️FIREPLACE ❄️COMFY❄️IMMACULATE ❄️SUPERHOST RATED OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️ 🏂Pico-5 minutes ⛷️ 🏂Killington-15 minutes 🥾Minutes from LT/AT 💍Wedding Venues 🚴Mtn Biking •Squeaky Clean •Fireplace, WIFI •TV in living room & bedroom •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children.

Guest favourite
An open-concept living area is seen, featuring a fully equipped kitchen with a breakfast bar. Warm wood accents and cozy seating are highlighted, while a decorative sign with a ski theme adds character to the space. Natural light filters in through large windows.
Condo in Ludlow
4.92 out of 5 average rating, 157 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.

Guest favourite
A cozy living area is furnished with a grey sofa and two patterned chairs. A wooden coffee table sits center stage, complemented by a stone fireplace. A large television is positioned on a wooden media console, while sliding glass doors offer access to an outdoor balcony, revealing greenery.
Condo in Killington
4.93 out of 5 average rating, 201 reviews

Newly renovated ski retreat at Killington

Located at Mountain Green Resort, Building III. Walk to Snowshed Lodge to begin your day of skiing, or take the free shuttle that will pick you up outside the entrance. After your day of skiing ends and you return to the unit, to experience the many amenities that the resort has to offer: indoor pool, eucalyptus steam room, two spas, sauna, fitness center,. You may prefer to stay in the unit and watch skiers come down the mountain. check VRBO.1532508 mention this for a better deal

Guest favourite
A spacious living area features a large stone fireplace with a flat-screen television mounted above. Comfortable seating is arranged around a wooden coffee table, creating an inviting space. In the background, the kitchen and dining area are visible, offering a seamless connection to the living space.
Condo in Killington
4.95 out of 5 average rating, 105 reviews

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Ski On-Ski Off!! Beautiful remodeled condo is in the heart of Sunrise at Bear Mountain. The designer kitchen features granite counter tops and top of the line stainless steel appliances. The main focal point in the living room is a massive stacked stone fireplace with a flat screen on the mantel. Recent upgrades include new living room furniture, master bed room furniture & updated tile in both showers. Additionally I own the adjoining unit & if you want more info see below

Top Guest favourite
A spacious living area features large windows allowing natural light to fill the room. A comfortable sectional sofa is arranged around a coffee table, and a TV is positioned near a wood-burning fireplace. A decorative artwork of a bull's head adorns the wall.
Condo in Killington
4.97 out of 5 average rating, 152 reviews

#45 Luxury Ski & Summer Condo with Private Sauna

Contactless checkin steps from Killington Skiing/ Mountain Biking/ Adventure Center, refurbished ski-home condo with its own private sauna, hotel-style condo amenities, excellent common area (pool, jacuzzi, showers, etc) in idyllic central Vermont. Travel guide provided after booking! The resort includes an indoor pool, two hot tubs, pool table, treadmills, and is nestled at the base of the mountain with its own ski-home trail (or mountain bike-home in the summer).

Superhost
A living room is furnished with a comfortable brown sofa and an armchair beside a wooden coffee table. A rustic wooden fireplace is adorned with festive garland and a flat-screen TV is mounted above it. Natural light enters through a large window, providing a cozy ambiance.
Condo in Killington
4.85 out of 5 average rating, 205 reviews

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

This rustic Mountain Green Resort condo offers easy access to ski/mtn bike lifts with resort style amenities. Features include 4K Smart TVs, High speed WiFi, private balcony with mountain views, board games, and full kitchen. On-site health spa including pool, sauna, hot tub, gym, masseuse. Restaurants and nightlife are minutes down the road. Restaurant/bar and ski/rental shop also within resort. Free shuttle to lifts available during ski season.

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
4.94 out of 5 average rating, 151 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.

Superhost
Aerial view of the Mtn Green Resort complex, surrounded by a blanket of fresh snow. The snow-covered mountains in the background and the tree-lined foreground offer a serene winter landscape. Several condo buildings are visible, showcasing multiple stories and a mix of windows.
Condo in Killington
4.78 out of 5 average rating, 101 reviews

3BR Mt Green Condo Minutes from the Slopes!

Our 3 bed/2 bath unit is located within Mountain Green Resort, steps away from everything! Take the free shuttle to the resort and ski home! Mtn Green is undergoing roof replacements and interior work from fall 2024 to Fall 2025. Located next to Killington Golf Course, near Killington Adventure Center, and across the street from Killington Resort and the slopes of Snowshed Lodge. Sleeps up to 8 guests. Fully equipped kitchen and bath.

Guest favourite
A view of the snow-covered path leading to the ski slopes is framed by the C Building’s balconies. Sunlight casts long shadows across the pristine snow, highlighting the tranquil winter scene. The surrounding area is clear and inviting, with ski signage visible in the distance.
Condo in Ludlow
4.92 out of 5 average rating, 148 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.

Top Guest favourite
The living area features a cozy fireplace surrounded by stone, with a wooden mantel. A dining table with white chairs is positioned near the kitchen, complemented by bar stools at the counter. Light floods in through large windows, enhancing the open layout.
Condo in Ludlow
4.95 out of 5 average rating, 103 reviews

Winterplace - Steps away from Slopes

Newly updated condo at Winterplace Okemo. This sunny corner 3 bedroom unit is just steps to the top of the A-B Quad. Completely renovated from floors to ceiling The delightful fireplace place will keep you toasty in the cozy living area. Outdoor ski locker just outside back door. Front door parking, and firewood included. Pool is open and available to renters all year. Hot tub in winter months and tennis courts in summer.

Top Guest favourite
A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.
Condo in Killington
4.96 out of 5 average rating, 151 reviews

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

Popular amenities for Windsor County condo rentals

Kitchen
Wi-Fi
Pool
Free parking on premises
Air conditioning

Weekly condo rentals

Top Guest favourite
A spacious living area features a cozy arrangement of a grey sofa and brown leather recliner, complemented by a woven coffee table. A stone fireplace is situated against a wooden wall, with a large television mounted above. Natural light enters through window treatments.
Condo in Ludlow
5 out of 5 average rating, 32 reviews

2 BR/2BA Ski In/Ski Out Condo on Okemo- Sleeps 6

Superhost
A spacious multi-story building is displayed, featuring a light yellow exterior and large windows. The surrounding area is covered in a fresh layer of snow, and a gravel path leads to the entrance. Two figures are seen walking in the snowy landscape.
Condo in Ludlow
4.75 out of 5 average rating, 8 reviews

Serene 1-BR Ski-In/Ski-Out Retreat on Okemo Mtn.

Top Guest favourite
A cozy living area features a spacious sectional sofa and a wooden coffee table, with candles placed on top. Artwork depicting mountain scenes decorates the wall, while a glass door leads to the private balcony, allowing natural light to brighten the space.
Condo in Mendon
4.93 out of 5 average rating, 60 reviews

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

Top Guest favourite
The open-concept living area is illuminated by an elegant chandelier, featuring comfortable seating with decorative pillows arranged around a wooden coffee table. A gas fireplace is visible, alongside a flat-screen TV and a well-equipped kitchen area in the background.
Condo in Killington
4.96 out of 5 average rating, 85 reviews

Bright & Cozy Ski-in Condo with Mountain View

Guest favourite
A comfortable living area is highlighted by a cozy leather sofa and a rustic coffee table on a soft area rug. A flat-screen television is mounted above a gas fireplace, while large glass doors lead to an outdoor patio, allowing natural light to fill the space.
Condo in Cavendish
5 out of 5 average rating, 8 reviews

Castle Retreat – Pool, Spa & Mountain Adventures

Guest favourite
A spacious lawn features well-maintained green grass, surrounded by lush trees and shrubs. Comfortable seating options are provided with classic outdoor chairs positioned near a flower garden, inviting relaxation in a serene, private outdoor space.
Condo in Quechee
4.88 out of 5 average rating, 95 reviews

Condo on Quechee Golf Course with Private Feel

Guest favourite
A spacious living area is highlighted by a U-shaped sectional sofa in gray upholstery. Two round wooden tables are positioned in front, and the kitchen area with modern appliances and cabinetry is visible in the background. Soft lighting and contemporary art add character to the space.
Condo in Mendon
4.84 out of 5 average rating, 50 reviews

Killington Vermont Modern luxury 2 bedroom Condo

Guest favourite
An aerial view of the Trail Creek development, showcasing a cluster of buildings surrounded by vibrant autumn foliage. Key landmarks, including the Ski Home Trail and Sports Center, are highlighted. The distance to the hotel and lifts is emphasized for easy navigation.
Condo in Killington
4.9 out of 5 average rating, 87 reviews

Luxe Trailside Ski On/Off. Next to hot tub

Pet-friendly condo rentals

Guest favourite
Condo in Bridgewater
4.96 out of 5 average rating, 47 reviews

Foliage and Ski Retreat by Woodstock & Killington

Superhost
An open living area is showcased, featuring a leather sofa in a neutral tone and a rustic wooden coffee table. A mounted television is positioned above a cozy stone fireplace. The adjoining kitchen area is visible, along with a wooden dining table that seats four.
Condo in Killington
4.72 out of 5 average rating, 120 reviews

Killington Tree House: 2 Room Modern Condo 432

Guest favourite
A cast iron gas fireplace is centered on a stone hearth, providing warmth. A wooden ladder holds colorful blankets, while a woven basket filled with magazines is placed nearby. Light filters in through a window with horizontal blinds, enhancing the cozy ambiance.
Condo in Ludlow
4.9 out of 5 average rating, 39 reviews

Fully walkable 2BR condo in Ludlow’s village!

Guest favourite
Condo in Plymouth
4.94 out of 5 average rating, 31 reviews

Charming Vermont Hideaway (Unit 2)

Superhost
A comfortable living space is depicted, featuring a cozy fireplace adorned with a mantle. A spacious sectional sofa is complemented by a decorative area rug. A coffee table occupies the center, while modern entertainment options are displayed on a dark wooden cabinet with a flat-screen TV.
Condo in Hartford
4.85 out of 5 average rating, 13 reviews

Cozy Fireplace, Pets, Club Access! - Saltbox 9A

Guest favourite
A modern kitchen area features a gray dining table surrounded by four black metal chairs. A wall clock hangs above the table, while white cabinetry and appliances are visible in the background. Natural light brightens the space, creating a clean and inviting atmosphere.
Condo in Hartford
4.91 out of 5 average rating, 47 reviews

Christian Street Condo #2 w/ Screened In Balcony

Guest favourite
An open living space features a bright red sofa with decorative pillows, complemented by a warm wood dining area with stools. The kitchen, equipped with stainless steel appliances, is visible in the background. Soft lighting creates a welcoming ambiance throughout the suite.
Condo in Killington
4.9 out of 5 average rating, 248 reviews

A Sweet Suite! Modern. Pool. 2RM/2BA. Shuttle. 532

Superhost
A comfortable living area features two sofas and a coffee table positioned in front of a brick fireplace. A television is mounted above the fireplace. Large windows allow natural light and offer views of the surrounding greenery.
Condo in Killington
4.7 out of 5 average rating, 30 reviews

Cozy killington condo- 5 min to killington resort

Condo rentals with a pool

Top Guest favourite
Condo in Killington
4.98 out of 5 average rating, 54 reviews

Luxury Condo - with Garage Parking and Pool

Guest favourite
The exterior of the building is shown against a backdrop of a green and orange hillside. Surrounding landscaping includes neatly trimmed bushes, with a paved parking area featuring two parked cars. The structure has a mix of stone and brick accents, complemented by gray roofs.
Condo in Mendon
4.88 out of 5 average rating, 112 reviews

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

Guest favourite
A welcoming living area features a cozy sofa and two armchairs arranged around a coffee table. A mounted TV is positioned above a wood-burning fireplace. Natural light filters through large windows with sheer curtains, highlighting the warm tones of the wood ceiling.
Condo in Killington
4.95 out of 5 average rating, 20 reviews

Northlands at Trail Creek

Top Guest favourite
The living area features a cozy seating arrangement with a brown couch and recliners, complemented by a decorative area rug. A coffee table sits in front of the seating, and a dining table with wooden chairs is positioned nearby. Soft lighting enhances the welcoming ambiance.
Condo in Killington
4.95 out of 5 average rating, 264 reviews

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!

Guest favourite
The spacious living and dining area features a large rug with geometric patterns on a neutral carpet. A wooden dining table with several chairs is visible, along with comfortable seating in the form of black leather chairs. A staircase leads to an upper level.
Condo in Mendon
4.87 out of 5 average rating, 54 reviews

2 Bedroom Pico/Killington Loft Condo at FoxHollow

Superhost
A spacious living room is captured with comfortable seating arrangements, including a large blue sectional sofa and a patterned armchair. Natural light filters through large windows, illuminating the cozy wood-burning fireplace. A wooden coffee table sits centrally, and shelving units display books and decorative items.
Condo in Killington
5 out of 5 average rating, 4 reviews

Enjoy our spacious 3 bed/3 bath Highridge B1 Condo

Guest favourite
The exterior of the Mountain Green building is visible, surrounded by snow-covered ground and trees. A clear blue sky complements the scene. A prominent sign marks the property, showcasing various services and property listings. Vehicles are parked nearby, indicating accessibility.
Condo in Killington
4.85 out of 5 average rating, 13 reviews

Killington Getaway 2bed/1.5 bath

Superhost
Aerial view captures a large cluster of buildings nestled among vibrant autumn foliage, showcasing shades of orange, yellow, and green. Majestic mountains rise in the background, while a spacious parking area is visible, surrounded by trees.
Condo in Killington
4.87 out of 5 average rating, 106 reviews

Updated large condo across from AT and skiing

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