
Holiday rentals with a pool in Winhall
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Top-rated rentals with a pool in Winhall
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

Walk to Mt. Snow-Spa-Summer Pool
*Exterior construction on siding until end of May *Amenity rich studio only a 5 min walk to Mt. Snow's famed Magic Carpet (runs on weekends) *Gas Fireplace *Queen memory foam Murphy bed *Queen pull out with memory foam mattress *Well appointed kitchen *65" curved UHD TV *25Mbps Wifi *USB wall outlets *Blue tooth music streaming to TV *Ample closet space *Patio with rocking chair *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger

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.

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

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton
Situated at the edge of protected forest land,this stay is a match for those who are seeking privacy to get away from the chaos of urban life and to decompress.How ? Enjoy the private and heated pool(until Sep15) during the day,and hang out by the outdoor fire pit when the sun is setting,and finish your evening off at the enclosed and brand new sea-salt hot tub!You will smell changes in the air as you drive through the trees,and you will hear the birds instead of the sirens when you are here.

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.

Premier Stratton Village Location - Pool & Hot Tub
-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.

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”.

Beautiful rustic woods and fields retreat.
Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment/ mini house. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $50 per trip per dog

MountSnow ski on/off condo in Vermont
Pool and Sports Center is open. Hours vary by day BBQ available for use by the outdoor pool pavilion On Mount Snow, Across from the Tin Lizzy trail leading to the Sundance Base Lodge and access to the Seasons Pass trail leading back to the condo. Very unique Condo in seasons as it has high vaulted ceilings. Condo is a 2 bedroom, 2 bathroom with 2nd bedroom on 2nd floor. Plenty of tennis and pickleball courts Best parking on the mountain

Winter Dream! The Handle Lodge at Snowtree Condos
The Handle Lodge at Snowtree Condos is a modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with friends and family. Make a meal in the beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge.

Mt Snow Chalet: Peaceful Escape w/Hot Tub
Escape to the serene beauty of Vermont's Green Mountains at the Mount Snow Chalet, a charming retreat nestled on a private wooded lot in the desirable Chimney Hill community of Wilmington. 🏠🌳 Just minutes from the slopes of Mount Snow, our chalet offers the perfect blend of rustic charm and modern amenities for an unforgettable getaway. Designed with love and care, we invite you to relax and stay awhile! 🥰
Popular amenities for Winhall rentals with a pool
House rentals with a pool

Magical Farm Getaway - a must visit!

The 1770 House

Adams Farm-"The Little Farmhouse"

Spring Skiing in VT Relax-Hot Tub-Sauna-wood stove

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Idyllic Dorset Home: Serene Escape w/amazing views

The Overlook - Manchester Mountain Masterpiece!

Woodsy Retreat Near Skiing, Private Pool in Summer
Condo rentals with a pool

Stratton Long Trail House: Quick Walk to Lifts!

Mount Snow Ski Chalet

Seasons @ MT Snow- Ski home, Walk to lifts, Pool

Perfect 3 Br. Getaway Condo in Stratton, Vermont!

Renovated Stratton Mtn Studio | Walk to Lifts

Ski in-out Seasons Condo on mtn-sports center-pool

One Bedroom Suite Near Okemo

Four Seasons Slope-side Getaway at Mount Snow
Other holiday rentals with a pool

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

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

The Best Vermont Has to Offer!

Quiet Retreat w/Pool/Near Saratoga /Lake George

Dream Catcher Farm

Lodge on the Loop: pet-friendly, hot tub & sauna

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

Bright 3B/2.5B Stratton Condo- Amazing location!
When is the best time to visit Winhall?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $910 NZD | $777 NZD | $800 NZD | $873 NZD | $643 NZD | $590 NZD | $512 NZD | $602 NZD | $590 NZD | $632 NZD | $957 NZD | $1,116 NZD |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Quick stats about holiday rentals with a pool in Winhall

Total holiday rentals
Explore 40 holiday rentals in Winhall

Nightly prices starting at
Winhall holiday rentals start at $367 NZD per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Winhall holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winhall rentals

4.7 Average rating
Winhall stays receive an average rating of 4.7 out of 5 from guests
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- Rentals with pools Bennington County
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- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Killington Resort
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Mount Snow Ski Resort
- West Mountain Ski Resort
- Saratoga Spa State Park
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- National Museum of Racing and Hall of Fame
- Dartmouth College
- Montshire Museum of Science
- Emerald Lake State Park
- Mount Sunapee Resort
- Congress Park




