
Home rentals with a pool near Okemo Mountain Resort
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool near Okemo Mountain Resort
Guests agree: these stays are highly rated for location, cleanliness, and more.

Topridge 3BR w Incredible View & Private Hot Tub!
Oso Dream provides AMAZING panoramic views of Bear Mountain. Step out the front door and ski down Sundog trail to Sunrise Village Triple or step out the back door and hop onto Bear Cub trail to access Bear Mountain! Enjoy the amenities within the complex including indoor & outdoor heated pool (seasonal), sauna and gym. Guests also have access to the outdoor skating rink and xc ski trails (weather permitting). Free use of ice skates, puff hockey equipment, snow shoes, xc skies, poles and sleds!

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna
Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Pool and Spa area closed May 4 to May 15 for annual Maintenance

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.

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.

Adams Farm-"The Little Farmhouse"
A Clean Ranch style home with hardwood floors located on a 100-acre Historic Vermont Farm. Retired farmers live in separate farmhouse & are available throughout your stay. Conveniently located just minutes away from MT Snow Ski Resort, Hermitage Resort, Stratton Mt. for Skiing, Snowboarding, Tubing, Hiking & Mountain Biking. 3 miles from downtown Wilmington. Minutes to public beaches and lakes. Use our trails for snowshoeing, X-Country Skiing or hiking. Our Pool is avail July -Labor day

Mid-mod VT Dream Chalet near skiing, lake & forest
Surround yourself in nature and cozy modern comfort. The romantic mid-mod-styled chalet backs to 10 acres of peaceful forest yet is just 12 min drive to Mount Snow for great skiing. 3 min. to the boat launch of gorgeous Lake Whitingham where you can rent jetskis & boats or go swimming & fishing. Hike trails to the charming town of Wilmington with its coffee shops & restaurants. Pools & hot tub up the road at clubhouse. Just steps away from iceskating, pickleball, hiking & snowmobile trails.

Moon Valley Country Retreat no clean fee pets yes
Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Cozy Vermont Antique Sugar House with Fireplace
Enjoy a peaceful and unique stay at this beautiful 1796 Sugar House. Luxury bedding, cozy fireplace, soaring timbers to a cathedral ceiling make this a special place. There is a Queen size bed on the main floor and twin beds in the sleeping loft accessible by a ladder. Try some of our wonderful local restaurants and shops. Lots of hiking trails to explore. Winter sports all around, or just enjoy some hot chocolate, a fire, and a good book. You are sure to enjoy the “Sugar House”.

AC • Vermont Retreat • Dogs Welcome • Pool & Spa
Coffee on the patio. Mountains turning gold. Your dog already halfway down the trail. That’s summer and fall at The Woods. This spacious dog-friendly 2BR sleeps 6 and features a full kitchen, fireplace, private deck, and access to the indoor pool, hot tub, and spa. Minutes from Killington Bike Park, hiking, golf, and restaurants, it’s the perfect home base for Vermont adventures. Bring the crew. Bring the pup. This is the place guests rebook before checkout.

⭐️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.

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.

Beautiful Spacious Condo at Killington Resort
This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!
Popular amenities for rentals with a pool near Okemo Mountain Resort
House rentals with a pool

Luxury Condo Tucked in the Heart of Killington

Magical Farm Getaway - a must visit!

Steps to Golf and Mountain Biking

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

Ranch at Mendon Mt Orchards

The Brick House on Washington Street

Luxurious family retreat home in the mountains

Hollywood Bungalow in the Berkshires #C0191633410
Condo rentals with a pool

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

Summer Dream! The Handle Lodge at Snowtree Condos

Bike park open Cozy 2 Bedroom .2 mi to lift

One Bedroom Suite Near Okemo

Newly renovated ski retreat at Killington

Luxe Trailside Ski On/Off. Next to hot tub

Walk to Mt. Snow-Spa-Summer Pool

#45 Luxury Ski & Summer Condo with Private Sauna
Other vacation rentals with a pool

Ski-in/out Jackson Gore Studio w/Kitchen

Charming 2-Bedroom Ski-In/Ski-Out at Jackson Gore

Idyllic Dorset Home: Serene Escape w/amazing views

Cozy Mountain-style Condo by Okemo with a View!

Stratton ski/walk on/off, King beds, FP, Hot tub

Ski on/ski off with hot tub

Modern Cottage between Stratton and Mount Snow VT

Summer in the mountains!
Quick stats about rentals with a pool near Okemo Mountain Resort

Total vacation rentals
Explore 140 vacation rentals in Okemo Mountain Resort

Nightly prices starting at
Okemo Mountain Resort vacation rentals start at ﺩ.ﺇ 367 per night before taxes and fees

Verified guest reviews
Over 1,860 verified reviews to help you choose

Family-friendly vacation rentals
120 properties offer extra space & kid-friendly amenities

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wi-Fi availability
140 of Okemo Mountain Resort vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Okemo Mountain Resort rentals

4.8 Average rating
Okemo Mountain Resort stays are highly rated by guests—averaging 4.8 out of 5!
Destinations to explore
- Rentals with a washer and dryer Okemo Mountain Resort
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- Condo rentals Okemo Mountain Resort
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- Rentals with pools Vermont
- Rentals with pools United States
- Lake George
- Stratton Mountain
- Killington Resort
- Pats Peak Ski Area
- Monadnock State Park
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Stratton Mountain Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Dartmouth College
- Middlebury College
- Bromley Mountain Ski Resort
- Mount Sunapee Resort
- Montshire Museum of Science
- Emerald Lake State Park
- Trout Lake
- Mount Monadnock
- Warren Falls
- Camp Plymouth State Park





