Vacation rentals with a pool in Winhall

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Winhall

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Dover

4.99 out of 5 average rating, 100 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

The Handle Lodge at Snowtree Condos is a charming and 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 family and friends. Make a meal in the new and 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. Check us out on IG for more content: @TheHandleLodge

Oct 4 – 11

R3,139 ZAR per night

Guest favorite

Apartment in Wilmington

4.97 out of 5 average rating, 126 reviews

The Loft @ Adams Farm-a great stay near Mt. Snow

Spacious & clean in Historic Duplex Farmhouse located minutes from MT Snow Ski Area & Stratton for Skiing, Snowboarding & Tubing. VAST trails just across the road. Shop & eat in the quaint villages of Wilmington & Dover. Private entrance and 3-stories of space with farmstyle decor & lovely views. 0ver 100-acres for you to Snowshoe , X-Country ski or just hike & explore. Plenty of parking for snowmobile trailers. Walking distance to Local Farm Store. Our pool is available July 1-Labor Day

May 7 – 14

R2,284 ZAR per night

Guest favorite

Guesthouse in Granville

4.9 out of 5 average rating, 786 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Near Lk George, Lk Champlain, Saratoga, Manchester & Rutland, VT. Hiking, fishing and swimming 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 recommended in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Dec 16 – 23

R1,967 ZAR per night

Superhost

Cabin in Wardsboro

4.8 out of 5 average rating, 203 reviews

Log Cabin Near Stratton/Mt Snow

Rustic log cabin for those looking for a getaway and a real Vermont experience. Pets allowed with *PET FEE* - add to your reservation There is Wifi &cell service (AT&T, Verizon). Please be aware this is not a luxury cabin, it is an authentic log cabin that we enjoy as a family during all seasons. No cable television - there is a TV with a Chromecast that you can use to stream from your phone over wifi. Firewood not provided 20 minutes to Stratton and 15 minutes to Mt. Snow

Aug 17 – 24

R3,091 ZAR per night

Guest favorite

Cottage in Newfane

4.99 out of 5 average rating, 177 reviews

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”.

Sep 5 – 12

R2,878 ZAR per night

Superhost

Cabin in Wardsboro

4.91 out of 5 average rating, 207 reviews

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow

Large Log cabin home (3,000 Sq ft) located midway between Stratton Mountain and Mt Snow and near the town of Dover. There is plenty of space for you and your nearest and dearest in this 4 bed/4 bath home. Whether you are entertaining friends and family in the open-concept living and dining space, quietly curled up with a book in front of the cathedral fireplace, or enjoying a relaxing soak in the outdoor hot tub after a long day on the slopes—this place has something for everybody!

May 27 – Jun 3

R5,222 ZAR per night

Guest favorite

Home in Peru

4.92 out of 5 average rating, 139 reviews

Beautiful Bromley/Manchester VT Retreat w/hot tub

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. Comfortably accommodates 12 people. Perfect for 2 or 3 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

Oct 15 – 22

R9,045 ZAR per night

Guest favorite

Guesthouse in Williamstown

4.93 out of 5 average rating, 219 reviews

Perfect Base for Your Berkshire Adventure

Charming private cottage with shared pool use. This newly renovated garden studio features high ceilings, a separate kitchenette with granite counters, mini fridge, microwave, queen sized bed, and rustic Arts & Crafts furniture. Located in a separate outbuilding, the cottage is close to woodland hikes, excellent biking, as well as many other attractions in the Berkshires. The beautiful in-ground pool is perfect for an afternoon dip - guest hours are usually between 3-5.

Sep 10 – 17

R3,467 ZAR per night

Guest favorite

Apartment in Clarendon

4.92 out of 5 average rating, 133 reviews

Vermont Horse Farm

Enjoy a morning cup of coffee on the patio overlooking the horse pastures or an evening by a fire under the gazebo with a fire pit on this idyllic Vermont horse farm with glorious views. Close to many activities, such as hiking, skiing and swimming. Scenic retreat on a family owned and working farm. Here we have horses, donkey, chickens, goats, and of course our dogs and cats. There is a short hiking trail with beautiful views and a picnic table by the stream.

Jun 26 – Jul 3

R1,838 ZAR per night

Guest favorite

Farm stay in Shaftsbury

5.0 out of 5 average rating, 111 reviews

Wing & A Prayer Farm

Each season at Wing & A Prayer Farm will restore & reset your pace. Situated on a working fiber farm, there are a variety of sheep, goats, alpacas, miniature donkeys, an American Guinea hog named "Princess Peppermint", and poultry-aplenty that decorate the landscape. The privacy of your own shady-glade & glimpses into farm life make this getaway just right. Comfortable, authentic farm coziness with traditional conveniences supports travelers from all walks.

Jul 9 – 16

R4,020 ZAR per night

Superhost

Condo in Stratton

4.88 out of 5 average rating, 107 reviews

Perfect Location! Steps to Village and Mountain

One-bedroom condo with beautiful rear-facing view of Mill Pond! Sleeps 4 with a Queen bed and a Full-size pull-out couch. Living room features a gas fireplace and smart TV (cable TV included; personal account required for Netflix and other streaming features). Access to pool, hot tubs, and sauna on-premises. Just steps away from the restaurants and shops in Stratton Mountain Village and the Base Lodge - no need to drive or wait for a shuttle!

Aug 20 – 27

R2,950 ZAR per night

Guest favorite

Barn in Newfane

4.97 out of 5 average rating, 124 reviews

Beautiful rustic woods and fields retreat.

Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment. 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 $80 per trip per dog

May 8 – 15

R2,568 ZAR per night