
Holiday rentals with a pool in Wardsboro
Find and book unique homes with a pool on Airbnb
Quick stats about holiday rentals with a pool in Wardsboro

Total holiday rentals
Explore 20 holiday rentals in Wardsboro

Nightly prices starting at
Wardsboro holiday rentals start at $127 SGD per night before taxes and fees

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Over 1,350 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Wardsboro holiday rentals include wifi access

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

4.7 Average rating
Wardsboro stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Wardsboro
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

~10% OFF~Walk To Mountain~Amenities
⭐️"Beautiful place in a great location - recently renovated, super clean and across the street from town." ⇒ Center of Stratton Village, walking distance to restaurants, shops, and the lifts🚶♂️🏔 ⇒ Private balcony with amazing views 🌅 ⇒ Dedicated workspace 📝 ⇒ Gas fireplace 🔥 ⇒ Fully equipped Chef's kitchen👩🍳 ⇒ Central AC/Heat ⇒ Onsite garage parking for 1 vehicle 🅿️ ⇒ Community amenities: pools, hot tubs, sauna, fitness center, tennis court, hiking trail, washer/dryer ⇒ 67 mbps Wifi

Great Amenities-Season Condo gym-sport center-pool
True ski in ski out ground floor condo w/ private entrance. Wood burning fireplace, wood included! King size bed in master, true Queen murphy bed, 1-memory foam cot, plus air mattress. Fully stocked & functional kitchen, including Keurig & Mr. coffee. Full bath w/blow dryer. Seating; kitchen counter, expandable table, wine barrel bar top. Walk out the door & down the steps to the NEW Sundance high speed lift. Take the Seasons trail home. Brand new state of the art Sports Center included.

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.

Modern Cottage between Stratton and Mount Snow VT
Escape to a Charming, newly Remodeled Chalet nestled perfectly between Mount Snow and Stratton,this cozy retreat is your ideal getaway—whether you're seeking outdoor adventure or quiet relaxation. Beautifully updated and full of charm, the chalet offers a peaceful setting with easy access to hiking, skiing, and everything Southern Vermont has to offer. Calendar Tip: If your preferred dates appear unavailable, feel free to reach out! The calendar typically opens just 2–3 months in advance.

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.

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

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”.

Log Cabin w/ Hot Tub & Fire Pit - Stratton/Mt Snow
Large Log cabin home 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!

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

Cozy 4BR Cabin | Pools & Hot Tub | Near Mt Snow
Escape to the mountains in this cozy 4BR, 2BA Chimney Hill cabin, just 15 minutes from Mt. Snow and minutes from downtown Wilmington. Gather around the outdoor fire pit, cozy up by 2 fireplaces, or enjoy access to the nearby community clubhouse with indoor & outdoor pools, hot tub, fitness room, and more. Sleeping up to 8, the home is perfect for families and groups looking for skiing, hiking, lake days, foliage, or a relaxing Vermont getaway year-round.

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

Walk to Mt. Snow-Spa-Summer Pool
*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 chairs *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger
Popular amenities for Wardsboro rentals with a pool
House rentals with a pool

Hollywood Bungalow in the Berkshires #C0191633410

Luxury Mid-Century Modern Vermont Home, Okemo View

Beautiful Bromley/Manchester VT Retreat w/hot tub

Ski Mountain View Estate

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

The Vermont Barn (Mount Snow)

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

Wander In | Close to Mount Snow & Stratton
Apartment rentals with a pool

Mt Snow Ski In/Out at Seasons

Slopeside Condo @ Seasons on Mt Snow (Ski-In/Out)

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Luxury Condo*Walk to Village*Hot Tub*Pool*Golf*MTB

Mount Snow Ski Chalet

Okemo Ski Condo, Steps from Trails. Modern & Cozy

One Bedroom Suite Near Okemo

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
Other holiday rentals with a pool

The Rooster - Mt Snow Townhome w/ Heated Pool!

Silver Brook Cabin

Sheldon Hill Chalet | 4BR Home by Mt Snow/Stratton

Snow Mtn Lodge- Mt Snow, Stratton, Pool, VAST

Skybarn Vermont: Pool, 100-Mile Views, Historic

Peaceful Ski Escape in Mountain Village

Mount Snow Best View - Sauna|HotTub|Pool|Fireplace

Summit’s Stratton Sneak Away II
When is the best time to visit Wardsboro?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $487 SGD | $545 SGD | $470 SGD | $378 SGD | $255 SGD | $265 SGD | $348 SGD | $355 SGD | $355 SGD | $331 SGD | $354 SGD | $520 SGD |
| 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 |
Destinations to explore
- New York Holiday rentals
- Montreal Holiday rentals
- Philadelphia Holiday rentals
- Boston Holiday rentals
- Quebec City Holiday rentals
- Portland Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Mont-Tremblant Holiday rentals
- Atlantic City Holiday rentals
- Newport Holiday rentals
- Providence Holiday rentals
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Killington Resort
- Fox Run Golf Club
- Rensselaer Polytechnic Institute
- Mount Monadnock
- Bromley Mountain Ski Resort
- Emerald Lake State Park
- University of Massachusetts Amherst
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- National Museum of Racing and Hall of Fame
- Mount Greylock
- Camp Plymouth State Park
- The Montague Bookmill





