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Apartment holiday rentals in Windsor County

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Top-rated apartment 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.
Apartment 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

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.
Apartment in Killington
4.89 out of 5 average rating, 247 reviews

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

The Suites at Killington is a 2RM/2BA suite in the heart of Killington. In the main suite, enjoy the open kitchen, dining and kitchen island, bathroom w/ tile shower, & cozy living area w/ sofa bed, queen bed, TV & patio. The primary bedroom offers a king/twin bed split, ensuite bathroom, TV, washer & dryer. Skiing or exploring, this suite offers a cozy retreat. Enjoy the heated pool (open June to mid-Sept). Unbeatable location with easy access to the best of Killington. Ski rental discounts.

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.
Apartment 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.
Apartment 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 visible, featuring a dining table surrounded by bright yellow chairs. A fireplace is seen, enhancing the space, while a large bear-themed wall mural adds a touch of nature. Natural light floods in from the nearby window.
Apartment in Killington
4.93 out of 5 average rating, 190 reviews

CozyCub - Pool, Hiking, Mountain Biking

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.

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.
Apartment 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.
Apartment 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

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.
Apartment in Killington
4.85 out of 5 average rating, 204 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.
Apartment 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.

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.
Apartment 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.

Superhost
A modern living area is presented with a cozy sofa and decorative throw pillows. A sleek wall-mounted TV rests above a rustic fireplace, with a stylish media console below. Light wood accents and a geometric patterned rug contribute to the inviting decor centered around comfort and relaxation.
Apartment in Killington
4.92 out of 5 average rating, 178 reviews

Renovated unit, prime location! Shuttle on/Ski off

We are located in Killington, VT. A newly renovated family friendly condo complex located on East Mountain Rd. Take the free shuttle (modified schedule post Covid) and end your day by skiing back to the condo. In the summer season you can enjoy a day mountain biking and ride home in just under five minutes. Enjoy the outdoor pool during the summer after a day of mountain biking! Year round activities all within a short distance.

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.
Apartment 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.

Popular amenities for Windsor County apartment rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

Weekly apartment 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.
Apartment in Ludlow
5 out of 5 average rating, 32 reviews

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

Superhost
A comfortable living area presents two couches arranged around a wooden coffee table. A gas fireplace serves as a focal point, while a large television is mounted on the wall. Glass doors lead to an outdoor space, allowing natural light to fill the room.
Apartment in Killington
4.78 out of 5 average rating, 18 reviews

Whiffletree base of Killington outdoor pool

Top guest favourite
A modern living room features a cozy fireplace, with decorative skis mounted above it. A large TV is positioned on a stylish media console, while a comfortable sofa and ottoman provide ample seating. Large windows allow natural light to brighten the space.
Apartment in Killington
5 out of 5 average rating, 38 reviews

Killington Condo-Indoor Pool/HotTub/FitnessCenter

Top guest favourite
A spacious living area features a comfortable sectional sofa, positioned near large windows that provide natural light and a view of the outdoors. A cozy fireplace with a wood-burning option adds a touch of warmth, accompanied by a flat screen TV and a small table with chairs.
Apartment in Ludlow
4.95 out of 5 average rating, 21 reviews

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

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.
Apartment in Quechee
4.88 out of 5 average rating, 95 reviews

Condo on Quechee Golf Course with Private Feel

Superhost
Apartment in Ludlow
4.78 out of 5 average rating, 9 reviews

Ski in/Ski Out- Okemo Clocktower base

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.
Apartment in Mendon
4.84 out of 5 average rating, 50 reviews

Killington Vermont Modern luxury 2 bedroom Condo

Guest favourite
A modern kitchen is equipped with stainless steel appliances, including a refrigerator, microwave, and oven. Green cabinetry adds a pop of color, while a wooden table provides a functional surface. The decor includes practical utensils and a decorative basket, enhancing the overall charm.
Apartment in Ludlow
5 out of 5 average rating, 13 reviews

Quaint 1BR Getaway: 4 Minutes to Okemo Mountain

Pet-friendly apartment rentals

Guest favourite
Apartment in Bridgewater
4.96 out of 5 average rating, 46 reviews

Foliage and Ski Retreat by Woodstock & Killington

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.
Apartment in Ludlow
4.9 out of 5 average rating, 39 reviews

Fully walkable 2BR condo in Ludlow’s village!

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

Charming Vermont Hideaway (Unit 2)

Superhost
A spacious room features two queen beds adorned with vibrant patterned comforters. A flat-screen TV is mounted on the wall. A window allows natural light to fill the space, while an air conditioning unit is positioned nearby. A wooden dresser and lamps add functional touches.
Apartment in Killington
4.59 out of 5 average rating, 109 reviews

NEW Killington Studio: Great Location! Comfy. 431

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.
Apartment in Hartford
4.85 out of 5 average rating, 13 reviews

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

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.
Apartment in Killington
4.7 out of 5 average rating, 30 reviews

Cozy killington condo- 5 min to killington resort

Top guest favourite
A spacious living area is highlighted by a stone-clad fireplace, surrounded by a large sectional sofa. Natural light filters through the draped windows, revealing a serene outdoor view. A rustic wooden shelf holds decorative items, and a stack of firewood is neatly arranged beside the fireplace.
Apartment in Killington
4.97 out of 5 average rating, 150 reviews

2 Bedroom Condo & Loft- POOL + Wine Bar/Cafe!

Top guest favourite
A serene sleeping area features a spacious bed with plush bedding, complemented by side tables on either side. A warm lamp casts a gentle glow, illuminating an artistic wall hanging that adds character to the room. Soft textures enhance the inviting ambiance.
Apartment in Ludlow
4.97 out of 5 average rating, 30 reviews

The Otto: A Warm and Cozy Ski In + Ski Out Lodge

Apartment rentals with a pool

Top guest favourite
Apartment 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.
Apartment in Mendon
4.88 out of 5 average rating, 112 reviews

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

Superhost
An inviting living space features a cozy sofa setup facing a wall-mounted TV. A warm ambiance is created by the fireplace beneath the TV. A modern kitchen island with bar stools complements the dining area, while large windows bring in natural light.
Apartment in Killington
4.74 out of 5 average rating, 77 reviews

Killington Vermont Luxury 2 bed condo

Guest favourite
A spacious living area is furnished with a dark brown sofa draped with a red throw blanket. A coffee table with a white surface is placed in front, complemented by a small green plant. The backdrop features a large mural of layered mountains, creating a serene atmosphere.
Apartment in Killington
4.92 out of 5 average rating, 59 reviews

Your Killington Basecamp:Free shuttle-Pool&Hot tub

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.
Apartment in Killington
4.95 out of 5 average rating, 264 reviews

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

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.
Apartment 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.
Apartment in Killington
4.85 out of 5 average rating, 13 reviews

Killington Getaway 2bed/1.5 bath

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.
Apartment in Killington
4.9 out of 5 average rating, 87 reviews

Luxe Trailside Ski On/Off. Next to hot tub

Destinations to explore