
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.

4BR Cabin with Hot Tub & Pools –15 mins to Mt Snow
Unwind in this cozy 4BR, 2BA retreat featuring a private hot tub, fire pit, game room, and access to indoor/outdoor pools, gym, and clubhouse amenities. Comfortably sleeps 8 (King, Queen, Full + trundle, bunk room) and includes a Pack ’n Play for little ones, perfect for families and groups. Whether you’re here for skiing, hiking, lake days, or fall foliage, enjoy the perfect blend of mountain charm, modern comfort, and unbeatable location near Wilmington’s shops, dining, and outdoor adventures.

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

Ski Mountain View Estate
Have fun in Vermont with the whole family at this peaceful off the grid feeling private home. Come see the amazing, scenic views Vermont has to offer. We are located minutes to some great ski mountains if you are looking to ski or snowboard. Love hiking? Enjoy hiking right out back of our home. Great time for the kids and parents to have a sledding party with a fire and views. Then relax in the new hot tub right off the deck. Always plenty of firewood for the pit! Great multi family getaway

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.

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.

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”.

⭐️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.

Dog-Friendly | Bike, Ski & Relax
In winter, you’re just 488 feet from the Sunrise lift. In summer, you’re minutes from one of the best mountain bike parks in the country, with the outdoor pool and hot tub reopening every Memorial Day. Sunrise Village is a true four-season resort, and this quiet, dog-friendly condo is one of its best spots. Whether you’re chasing powder days, peak foliage, long bike weekends, or just a few peaceful days in the mountains, the location does all the work.

Steps to Golf!
Enjoy Killington at competitive pricing without sacrificing comfort! Located in Trail Creek Condo Association. • Ski, hike, bike, or golf just steps away • Cozy up by the wood fireplace (free wood) • Pool, hot tubs, sauna, and game room at community center • 6-minute walk to Snowshed or shuttle (winter weekends/holidays) • Ski home trail (snow-dependent) • Minutes to restaurants, bars, and shops • Convenient bus stop Adventure and relaxation await!
Popular amenities for rentals with a pool near Okemo Mountain Resort
House rentals with a pool

Stratton/Mt Snow minutes away! Hot tub + Game room

Luxury Condo Tucked in the Heart of Killington

Magical Farm Getaway - a must visit!

Solitude, 4 bedroom, ski in/out

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

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

Ranch at Mendon Mt Orchards

The Brick House on Washington Street
Apartment rentals with a pool

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

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

One Bedroom Suite Near Okemo

Newly renovated ski retreat at Killington

Luxe Trailside Ski On/Off. Next to hot tub

Cozy condo within walking distance to the slopes.

Walk to Mt. Snow-Spa-Summer Pool

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

Mountain Vista 3-BR Haven at Jackson Gore Resort

Ski-in/out Jackson Gore Studio w/Kitchen

The Villa - Farmhouse with Hot Tub, Pool and Pond

Cozy Quechee Cabin near Woodstock and Killington

Dream Catcher Farm

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

Cozy Mountain-style Condo by Okemo with a View!

Dana Road House Sunlit VT Country Home w/HotTub
Quick stats about rentals with a pool near Okemo Mountain Resort

Total holiday rentals
Explore 140 holiday rentals in Okemo Mountain Resort

Nightly prices starting at
Okemo Mountain Resort holiday rentals start at $128 SGD per night before taxes and fees

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

Family-friendly holiday rentals
120 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
140 of Okemo Mountain Resort holiday rentals include wifi 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 fireplace Okemo Mountain Resort
- Rentals with a washing machine and dryer Okemo Mountain Resort
- Rentals with a kayak Okemo Mountain Resort
- Rentals with a sauna Okemo Mountain Resort
- Pet-friendly rentals Okemo Mountain Resort
- Fitness-friendly rentals Okemo Mountain Resort
- Rentals with a patio Okemo Mountain Resort
- House rentals Okemo Mountain Resort
- Ski-in/ski-out rentals Okemo Mountain Resort
- Apartment rentals Okemo Mountain Resort
- Flat rentals Okemo Mountain Resort
- Rentals with a hot tub Okemo Mountain Resort
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- Family-friendly rentals Okemo Mountain Resort
- Rentals with a firepit Okemo Mountain Resort
- Rentals with pools Vermont
- Rentals with pools United States
- Lake George
- Stratton Mountain
- Killington Resort
- Pats Peak Ski Area
- Monadnock State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Fort Ticonderoga
- Ragged Mountain Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Dartmouth College
- Middlebury College
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Sunapee Resort
- Trout Lake
- Southern Vermont Arts Center
- Warren Falls
- Mount Monadnock





