
Vacation rentals with a pool in Cavendish
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Cavendish
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Luxury Condo Tucked in the Heart of Killington
Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

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

Dog Friendly Mountain Condo w/Spa, Pool, Sauna
Escape from your suburban home and come enjoy our beautiful Killington getaway condo. Boasting a spacious, comfortably furnished interior, this modern 2-bedroom, 2-bathroom abode is perfect for families, multiple couples, or a romantic getaway. Our Killington Air BNB has far more than the average Air BNB with everything you need for a great experience. If you're working during your stay you'll find high speed wifi and a dedicated desk space so you can focus on business when not on the slopes

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”.

Serene Top Floor Condo (resort style amenities)
Welcome to Killington! We offer a year round accommodation with the convenience of walking to the lifts, free covered parking, private balcony, full kitchen, and 24/7 keyless entry. The Mountain Green condos have great seasonal amenities in our building such as indoor/outdoor pool, hot-tub, fitness center, ski rental , full service bar/restaurant, outdoor lockers. This is the ideal setup for anyone enjoying the mountain without driving to it!

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.

Right at Killington !
The only place closer to the Snowshed is the Grand Hotel. If you are young and agile you can walk to Snowshed Base - about 10 minutes. Welcom to Trail Creek Condo's. After the races enjoy indoor salt water pool or 2 hot tubs or hot sauna in the Trail Creek Amenities building (a couple of buildings away). Great for couples or families. We provide all linens, towels & firewood. FREE WIFI, cable and HBO. Fully stocked kitchen.

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!

Hotel Chic - Home Comfort -Ski Easy.
HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS OUR ULTRA COZY RETREAT WAITS JUST FOR YOU PERFECT WINTER RETREAT❄️ ⛷️ 🏂Pico-5 minutes ⛷️ 🏂Killington-15 minutes ❄️❄️SUPERHOST RATED❄️❄️ ❄️Squeaky Clean ❄️Fireplace, WIFI ❄️TV in living room & bedroom ❄️Adjustable queen bed ❄️Private covered porch ❄️Keypad check in ❄️Smoke free/Pet free NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children.

FirBear- Pool, Gym, Hot tub.
Revel in this bright and modern ski condo just off Killington's main road and close to everything. Relax after a day on the mountain streaming on one of your 3 smart TVs. Indulge with the fabulous condo amenities including the pool, hot tubs, spa, gym, and tennis courts, or settle in by the wood-burning fire. Spread out in this spacious condo and enjoy all that Killington has to offer.

Cozy Condo- Close to Mountain, Ski home trail
Experience Killington like never before with our ski-home condo and a free 5min shuttle ride to the mountain on winter weekends. Our home is the perfect location to experience all that Killington has to offer. It has a free shuttle and a ski home trail. As well as quick and convenient access to Killington's great nightlife including restaurants, shopping, bars, and entertainment.
Popular amenities for Cavendish rentals with a pool
House rentals with a pool

Magical Farm Getaway - a must visit!

Ranch at Mendon Mt Orchards

Adams Farm-"The Little Farmhouse"

The Brick House on Washington Street

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

Historic Home on 17 acres of land. Go escape!

New-Renovated, Large Private Deck - Fox Crossing

Luxurious family retreat home in the mountains
Condo rentals with a pool

Cozy Mountain Condo - Ski In/Ski Out

Renovated unit, prime location! Shuttle on/Ski off

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

Cozy Slopeside Studio at Pico

Best value in this Cozy 2 Bedroom .2 mi to lift

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking

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

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo
Other vacation rentals with a pool

Cozy Cabin - Lake, Ski, Golf!

Mt Snow 2 Bdrm Condo - Free Ski Shuttle

The Woods Renovated 1BR Studio close to the slopes

Cozy Quechee Corner Cabin

Cozy Mountain-style Condo by Okemo with a View!

Peaceful condo at Okemo - Direct Ski Access

Windfall~Condo @Quechee Lakes VT~ Golf. Ski. Renew

Quechee Acorn! VT at its best!
When is the best time to visit Cavendish?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ914 | ﺩ.ﺇ1,113 | ﺩ.ﺇ841 | ﺩ.ﺇ859 | ﺩ.ﺇ914 | ﺩ.ﺇ841 | ﺩ.ﺇ914 | ﺩ.ﺇ933 | ﺩ.ﺇ914 | ﺩ.ﺇ914 | ﺩ.ﺇ841 | ﺩ.ﺇ948 |
| 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 vacation rentals with a pool in Cavendish

Total vacation rentals
Explore 40 vacation rentals in Cavendish

Nightly prices starting at
Cavendish vacation rentals start at ﺩ.ﺇ404 per night before taxes and fees

Verified guest reviews
Over 950 verified reviews to help you choose

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

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Cavendish vacation rentals include wi-fi access

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

4.8 Average rating
Cavendish stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with pools Windsor County
- Rentals with pools Vermont
- Rentals with pools United States
- Okemo Mountain Resort
- Stratton Mountain
- Monadnock State Park
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Bromley Mountain Ski Resort
- Dartmouth Skiway
- Crotched Mountain Ski and Ride
- Whaleback Mountain
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Dorset Field Club
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- The Shattuck Golf Club
- Brattleboro Ski Hill
- Autumn Mountain Winery
- Northeast Slopes Ski Tow




