Condo holiday rentals in Cavendish

A cozy living space features a large window providing natural light. A comfortable couch and chair are positioned around a coffee table. The room includes a spacious bed with a blue and black patterned blanket, while a 50-inch TV is mounted on the wall.

4.88 out of 5 average rating, 266 reviews

Killington-Pico ski in/out Studio at base of Pico

At the base of Pico and 10 minutes from Killington. Free shuttle service from my place to Killington. I have a free ski locker and free wood for the fireplace. There is a laundry room with coin operated machines. There is a brand new 50” flat screen tv with cable. It’s a smart tv, that’s hooked up to WiFi, so you can use your Netflix, Amazon or Hulu account if you want. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for 1 day. No daily cleaning service. No parties.

The living area features high wooden beam ceilings and exposed brick walls, creating a rustic ambiance. A cozy wood burning fireplace is situated beneath the wall-mounted television. Comfortable seating includes a checkered sofa and a leather chair, all complemented by a central area rug.

4.96 out of 5 average rating, 151 reviews

Cozy Ski Condo In Historic Mill - on shuttle route

2 bedroom, 1 bathroom condo located in the historic Mill Building (1834). This top floor end unit offers views of Okemo Mtn while overlooking the Black River. With exposed brick walls, wooden beams, high ceilings & a wood burning fireplace we hope you enjoy the coziness of this rustic space after a long day of adventure. Firewood, linens, towels, & cooking needs are provided for added comfort. Our condo is centrally located, walkable to shops/restaurants & is on the shuttle route to Okemo.

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.

4.87 out of 5 average rating, 126 reviews

Updated large condo across from AT and skiing

Family friendly, large 3 bedroom condo across the street from hiking and skiing in Killington. WiFi, cable TV, large gathering areas, spacious bedrooms, updated kitchen, and unlimited free firewood in winter. Plenty of après-ski chic touches make this a stylish yet comfortable retreat. 2 minute drive to Pico, 2 min walk to Appalachian Trail! Whether skiing, hiking, playing tennis, swimming, or game nights and cooking at-home meals with friends, this updated condo is a perfect spot to get away.

A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.

4.99 out of 5 average rating, 172 reviews

Alpine Condo - AC & Pool - Golf & Bike

Updated 1-bedroom Whiffletree condo with stylish alpine feel—steps from Killington Resort, golf course, and access road. Thoughtfully stocked with essentials, plus a private gear locker for convenience. Relax at the onsite outdoor pool (open Memorial Day–Labor Day). Sleeps 4 with a king bed and queen pullout sofa. Portable AC unit in the living room helps keep the condo comfortable Pack & Play crib, mattress and sheets available upon request for $25 per stay. Reg #007718

A spacious living room features a real wood fireplace with a modern hearth, surrounded by a cozy seating arrangement. A flat-screen television is mounted above the fireplace. Large windows provide natural light and a view of the outdoor balcony, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 110 reviews

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed

Ski On-Ski Off cozy mountain condo with Real Wood Fire Place and King Size Bed in Sunrise Village on Killington Mountain. Updates include all new furniture in the Master Bedroom & Guest Bedroom, all new top of the line Stainless Steel Appliances in the gourmet kitchen, Tastefully decorated Living Room with new queen size sleep sofa & matching chairs. Simply walk to the end of the parking lot to the Ski On/Off trail. I own the adjoining unit -more info below.

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.

4.95 out of 5 average rating, 192 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.

A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.

4.78 out of 5 average rating, 334 reviews

Serene Top Floor Condo (resort style amenities)

Welcome to Killington! We offer a year round accommodation with the convenience of walking to the lifts, free covered parking, private balcony, full kitchen, and 24/7 keyless entry. The Mountain Green condos have great seasonal amenities in our building such as indoor/outdoor pool, hot-tub, fitness center, ski rental , full service bar/restaurant, outdoor lockers. This is the ideal setup for anyone enjoying the mountain without driving to it!

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.

4.96 out of 5 average rating, 116 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.

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.

4.93 out of 5 average rating, 175 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. Please note there is no AC at this condo complex summer time

A view of an open-concept suite showcases a kitchen countertop with a sink and decorative flowers. A cozy living area is visible, featuring a red sofa and a dining table. The master bedroom is visible in the background, fitted with a king bed and soft lighting.

4.93 out of 5 average rating, 123 reviews

One Bedroom Suite Near Okemo

This 675 square foot suite features a master bedroom with king bed and flat screen TV, separate living room with queen sleeper sofa, flat screen TV, and gas fireplace, full size kitchen, dining area, washer & dryer, and private bath with jetted tub. The Suites location in the Pointe hotel gives you access to the indoor pool, hot tub, fitness room and game room.

A spacious living area features a plush sofa, a wooden dining table with chairs, and a large window allowing natural light. An electric fireplace is positioned against a stone wall, and a smart TV is mounted above a media console. The decor includes subtle rustic elements.

4.95 out of 5 average rating, 173 reviews

AC | Dog-Friendly | Bike, Hike & Relax

Escape to the quieter side of Killington. Spring and summer are some of the best times to visit—fewer crowds, lower rates, and easy access to hiking, biking, golf, and everything the mountains have to offer. After a day outdoors, relax on the private balcony, unwind by the fireplace, or enjoy the resort amenities just minutes away.

A cozy living room features a large gray sectional sofa and plush armchair, inviting relaxation. A wooden coffee table sits in the center, with a textured throw draped casually over it. Natural light streams through multiple windows, enhancing the welcoming ambiance of the space.

4.98 out of 5 average rating, 161 reviews

Snowcub- AC, Pool, Hot tub, Tennis, Grill!

Your group will be close to everything when you stay at this centrally-located condo. Enjoy two bedrooms plus a loft for a variety of sleeping options. Condo amenities include pool, gym, spa, tennis and hot tub. You will be close to the bars, restaurants, market and coffee shops and just minutes to the Killington resort base areas.

Popular amenities for Cavendish condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly condo rentals

4.93 out of 5 average rating, 15 reviews

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

Castle Retreat – Pool, Spa & Mountain Adventures

The newly remodeled condo is situated in a historic Wool Mill building, characterized by a red brick facade. The building features a distinctive clock tower and multiple levels, with balconies visible on the second floor. Snow-covered ground enhances the winter scene.

4.98 out of 5 average rating, 48 reviews

Cozy at the Mill

A modern kitchen with a circular dining table surrounded by four wooden chairs is featured. Stainless steel appliances, including a microwave and oven, are present. A stylish light fixture hangs above the table, while the fireplace and sports equipment are visible in the background.

4.92 out of 5 average rating, 224 reviews

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

A spacious living area features a large sectional sofa and cozy bean bags, complemented by a wood-burning fireplace. Natural light enters through sliding glass doors that open to a view of the outdoors. A dining table is positioned nearby, enhancing the inviting communal space.

4.91 out of 5 average rating, 69 reviews

Cozy 1BR/1BA Condo

4.89 out of 5 average rating, 37 reviews

A cozy bedroom features a spacious bed adorned with a quilt. A large window allows natural light to filter through, complemented by soft curtains. There's a wooden dresser and a bedside table with a lamp, while a chair provides additional seating.

Condo in Cavendish

Condo at Castle Hill

4.96 out of 5 average rating, 175 reviews

A cozy living area features a pair of brown sofas with decorative cushions. A wooden coffee table is centered in front of the seating. Artwork is displayed on the light green walls, and a lamp provides soft illumination, complementing the natural light from the window.

Condo in Stratton

Cozy condo within walking distance to the slopes.

4.93 out of 5 average rating, 71 reviews

The living area features a modern design with a mounted television above a sleek electric fireplace. Plush seating includes a cozy couch and two armchairs, accompanied by a stylish coffee table. Light-colored curtains frame the windows, enhancing the room's bright ambiance.

Condo in Rutland

Luxury, downtown apt w/ balcony close to skiing

Superhost

A spacious living area is showcased, featuring comfortable leather sofas and a decorative wall clock. A television is positioned near a fireplace, complemented by a stone hearth. Natural light filters through two windows adorned with light fabric curtains, highlighting the wooden beams of the ceiling.

4.74 out of 5 average rating, 97 reviews

3-Bedroom Condo in the heart of the Village @Okemo

Pet-friendly condo rentals

4.96 out of 5 average rating, 57 reviews

Condo in Bridgewater

Foliage and Ski Retreat by Woodstock & Killington

4.97 out of 5 average rating, 150 reviews

A living area is presented with a spacious purple sectional sofa and an accent chair, creating a comfortable seating arrangement. A wooden coffee table occupies the central space, and large windows allow natural light to fill the room, revealing a snow-covered landscape outside.

Condo in Eastman

Cozy Light-filled Condo in Charming Eastman

4.86 out of 5 average rating, 35 reviews

Trailside Village #3: Ski In Ski Out 1BR. Hot Tub.

5 out of 5 average rating, 15 reviews

A comfortable living area is highlighted by a classic woodburning fireplace, flanked by an armchair and a patterned wingback chair. A media console sits adjacent to a window, allowing natural light to illuminate the space. Decorative rugs and warm lighting create an inviting environment.

Condo in Dorset

Dorset, Vermont mountain retreat

4.77 out of 5 average rating, 52 reviews

5 min to killington resort with cozy fireplace

4.94 out of 5 average rating, 51 reviews

Killington Summer - Hike, Bike, Fish, or Golf

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.

4.97 out of 5 average rating, 158 reviews

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

4.97 out of 5 average rating, 87 reviews

The exterior of a multi-story grey building is shown, featuring a sloped roof and several square windows. A ramp leads to the main entrance, which is adorned with light fixtures and framed by greenery, including bushes and grass.

Condo in Londonderry

Magical Ski-In/Ski-Out Condo at Magic w/ game room

Condo rentals with a pool

4.89 out of 5 average rating, 124 reviews

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

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

A view from the balcony showcases the surrounding landscape, highlighting green hills and clear blue skies. Two adjoining buildings are visible, featuring sloped roofs and a variety of architectural styles. The area appears tranquil, with open spaces and scattered trees enhancing the natural scenery.

4.95 out of 5 average rating, 214 reviews

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

4.9 out of 5 average rating, 105 reviews

A spacious living area is highlighted by large windows that provide a panoramic view of the surrounding hills. The room features a comfortable sofa, a wooden coffee table, and a dining set. A fireplace and a fully equipped kitchen are situated in the background.

Condo in Stratton

~10% OFF~Walk To Mountain~Amenities

A tranquil sleeping area features a cozy bed with soft bedding and accent pillows. Nightstands with lamps are placed on either side, providing gentle light. A large horse portrait adorns the wall above the bed, contributing to the serene ambiance.

4.91 out of 5 average rating, 109 reviews

Big Pool, Golf we are on the course 2 Bedroom

Superhost

The cozy living area features a stone fireplace and a 42" flat-screen TV mounted on the wall. Comfortable sofas are arranged around a wooden coffee table, with decorative pillows adding warmth to the space. Soft natural light enters through the nearby window, enhancing the inviting atmosphere.

4.8 out of 5 average rating, 113 reviews

Elegant 3BR Escape | Hiking & Nature Nearby

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.

4.94 out of 5 average rating, 231 reviews

Newly renovated ski retreat at Killington

4.89 out of 5 average rating, 101 reviews

Luxe Trailside Ski + Bike On/Off. Next to hot tub

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.