Home rentals with a pool near Okemo Mountain Resort

4.9 out of 5 average rating, 184 reviews

A spacious ski home is surrounded by snow-covered trees, featuring a modern design with a sloped metal roof. Large windows allow natural light to enter, while a gravel driveway leads to the entrance. This bustling wooded area provides a serene backdrop during winter.

Home in Peru

Beautiful Bromley/Manchester VT Retreat w/hot tub

"Manchester Moose!" Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester, Beautifully remodeled VT vacation getaway nestled in the Green Mountains. Closest skiing to quaint Manchester VT, minutes from snowmobiling, hiking, fine dining and shopping. This home features 5 bedrooms, 3 with queen beds including 2 Masters, and 2 bedrooms with double bunks. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains! YouTube video link @GreenMountainStay

4.99 out of 5 average rating, 101 reviews

A bright and airy great room features high wooden ceilings with large windows showcasing mountain views. A spacious sectional sofa is arranged around a colorful area rug, complemented by blue armchairs. Contemporary lighting and artistic decor add to the inviting ambiance.

Home in Springfield

Luxury Mid-Century Modern Vermont Home, Okemo View

The Brewster House is a premiere destination for skiing, hiking, enjoying the country or just lounging by the pool. Designed by renowned mid-century modern architect turned painter George W.W. Brewster, the Brewster House has been lovingly restored and updated, and filled with original, local art. With gorgeous views of Okemo and Hawks Mountain Wildlife Area, the Brewster House is close to incredible dining, great art galleries, and antique shops. Come bask in beauty and relax completely!

The living room features a high wooden ceiling and a large, central fireplace. Sofas and a loveseat provide ample seating, while artwork depicting skiing is mounted above the fireplace. Windows allow natural light to enter, offering a view of the outside.

4.94 out of 5 average rating, 106 reviews

Okemo Ski Condo, Steps from Trails. Modern & Cozy

Modern & cozy ski condo, sleeps 6. A short walk, 250 steps to the Sachem trail. Ski straight to Sunburst 6, & other lifts & avoid the lines and parking hassles at the base. A 5 minute drive to the main lodge & ski school. Great decor, fully furnished. Living room, new fireplace, master bedroom, bathroom with shower, washer & dryer. Loft with queen & 2 single beds upstairs. Wi-fi, cable, cooking utensils, towels & bedding. Firewood included. Common area for Ski's & Snowboards outside the door.

4.92 out of 5 average rating, 114 reviews

The spacious great room features a wood-burning fireplace and is furnished with two comfortable sofas and a wooden coffee table. A large flat-screen TV hangs on the wall, and natural light emanates from the surrounding windows. A dining area with a circular table is visible in the background.

Home in Ludlow

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

PLEASE NOTE: No Saturday arrivals or departures, no pets, no parties Recommended local activities & floor plans of our home can be found on our OkemoHouse site Our "Trailside Chalet" is ON OKEMO MOUNTAIN, a 200 yard walk downhill from the Sunshine Chairlift & Suncatcher ski trail on Okemo's Southface (open end if Dec - late Mar). This Classic Vermont Ski Chalet features 5 bedrooms, sleeps 12, and is on a private wooded lot overlooking a babbling brook with seasonal fire-pit & charcoal grill.

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, 112 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 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.

4.79 out of 5 average rating, 337 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!

5.0 out of 5 average rating, 18 reviews

Cozy & Inviting 3BR/2BA @ Winterplace

Your family and friends will love this renovated 3 BR/2BA Winterplace condo. Our family does! Just a 2 min walk to ski to lifts that will take you to the top. You won't have to haul gear from the parking lot to the lift or buy overpriced food at the lodge for lunch! Hungry? You can ski right back home. Tired? You can unwind by the fireplace or at the indoor pool with two hot tubs. Your mountain getaway for one or two families awaits!

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, 117 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 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.

4.93 out of 5 average rating, 247 reviews

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis

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.

Shipping container in Ludlow

Luxury Container Home Sauna-Heated Pool-Hot Tub

Escape to a luxury modern container retreat minutes from Okemo Mountain. Set on 3 private acres with mountain views, this unique getaway features a sauna, heated plunge pool and thoughtfully designed modern interiors. Perfect for skiing, hiking, fall foliage, or relaxing in nature, the home blends comfort, style, and privacy while still being close to restaurants, lakes, golf, and everything Ludlow has to offer year-round.

5.0 out of 5 average rating, 17 reviews

4.95 out of 5 average rating, 182 reviews

Ski-In/Out, Hot Tub, Pet-Friendly

Escape to a spacious, pet-friendly 1-bedroom mountain condo in Killington, comfortably sleeping 4. Enjoy year-round adventures with easy access to hiking, biking, golf, and skiing. The condo is 488 ft to the sunrise lift! Relax on your private balcony, by the gas fireplace, or at the resort's indoor/outdoor pools, hot tub, and fitness center. Perfect for a serene mountain getaway with all amenities.

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.

4.9 out of 5 average rating, 42 reviews

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

Experience the ultimate Okemo Mountain adventure in this 2-bed, 2-bath ski-in/ski-out condo at Winterplace. Perfect for families, this retreat features a wood-burning fireplace, a full kitchen, and access to a community indoor pool and hot tubs. Enjoy true slope-side convenience just steps from your door. Comfortably sleeps your group for a perfect mountain getaway.

Popular amenities for rentals with a pool near Okemo Mountain Resort

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 142 reviews

Home in Springfield

Ski Mountain View Estate

Superhost

Home in Killington

Luxury Condo Tucked in the Heart of Killington

4.86 out of 5 average rating, 260 reviews

4.89 out of 5 average rating, 141 reviews

Home in Killington

Golf and Mountain Biking outside the door!

Superhost

The exterior of a cozy ranch house is shown, framed by lush greenery and flowering shrubs. The front porch is accessible via steps, with a teal door welcoming visitors. A pathway leads through the manicured lawn, enhancing the inviting appearance of the property.

Home in Mendon

Ranch at Mendon Mt Orchards

4.87 out of 5 average rating, 283 reviews

4.92 out of 5 average rating, 172 reviews

Home in Killington

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

4.95 out of 5 average rating, 43 reviews

A cozy living area features a stone fireplace with a warm fire, surrounded by a modern sofa. Above the fireplace, a wall-mounted television is visible. A rustic chandelier with multiple bulbs hangs over a dining table, while decorative items are placed on a nearby side table.

Home in Ludlow

Ski-In/Ski-Out Hike Okemo Condo Solitude Village

4.82 out of 5 average rating, 61 reviews

A spacious living room is highlighted by a woodstove positioned on a brick platform. Comfortable seating includes a leather sofa and two patterned armchairs. Natural light filters through sheer curtains, illuminating framed artwork on the walls and a decorative rug on the carpeted floor.

Home in Ludlow

Beautiful Okemo Farmhouse 0.7 mile from base lodge

4.92 out of 5 average rating, 61 reviews

The exterior of a newly renovated retreat showcases a wooden structure surrounded by trees. A fire pit is set with several dark chairs arranged in a circular formation. Soft light emanates from the large windows, providing a glimpse into the warm interior spaces.

Home in Bridgewater

Luxurious family retreat home in the mountains

Condo rentals with a pool

A cozy living area features a stone fireplace, providing warmth and a focal point in the room. Two brown sofas are positioned around a coffee table. Soft lighting from a nearby lamp creates a comfortable ambiance, complemented by large windows letting in natural light.

4.93 out of 5 average rating, 503 reviews

Book Peep now Stay on Pico 1 Bedroom free shuttle

4.97 out of 5 average rating, 214 reviews

Condo in Stratton

Premier Stratton Village Location - Pool & Hot Tub

4.94 out of 5 average rating, 101 reviews

Bright & Cozy Ski-in Condo with Mountain View

Superhost

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

4.88 out of 5 average rating, 112 reviews

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.

4.91 out of 5 average rating, 227 reviews

Mtn Green Condo-Ski/Bike Lifts, Covered Parking

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, 110 reviews

Great PeeP rates Hike Golf Tennis 2 Bed on Mtn

4.96 out of 5 average rating, 182 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.

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, 216 reviews

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

Other holiday rentals with a pool

4.98 out of 5 average rating, 45 reviews

A warm living area features a stone fireplace as the focal point, complemented by wooden beams and walls. A gray sofa and a red armchair invite relaxation, while a wooden coffee table holds a stack of magazines. Large windows allow natural light to fill the space.

Chalet in Ludlow

Five Bedroom Family Home on Okemo with A.C. splits

5.0 out of 5 average rating, 17 reviews

Apartment in Ludlow

Cozy Mountain-style Condo by Okemo with a View!

4.9 out of 5 average rating, 10 reviews

A scenic outdoor space features wooden rocking chairs arranged around a circular stone fire pit, surrounded by colorful wildflowers. Towering trees provide shade, while the multi-story building stands in the background against a clear blue sky.

Apartment in Ludlow

Ski-in/out Jackson Gore Studio w/Kitchen

4.93 out of 5 average rating, 29 reviews

Apartment in Killington

Skier's Retreat | Hot Tub | Sauna | Free Shuttle

5.0 out of 5 average rating, 17 reviews

Home in Hartford

Cozy Vermont Cabin | Near Woodstock + Quechee

A cozy living area is highlighted by a plush, neutral-toned sectional sofa, complemented by a soft throw. A wooden coffee table rests nearby, with a candle casting a warm glow. Large windows allow natural light to enter, and a stone fireplace adds a touch of warmth.

5.0 out of 5 average rating, 70 reviews

Entire Condominium for your base camp

5.0 out of 5 average rating, 7 reviews

Apartment in Killington

Killington Sapphire