
Holiday 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!

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. Experience the charm and beauty of Killington like never before.

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.

Walk/Bike to Snowshed Lift 2BR @ Mt. Green Resort!
Our CLEAN & SPACIOUS 2 Bedroom and 1.5 Bath Condo is a corner unit in the 4 Season Mountain Green Resort which is located directly across the street from the Snowshed Base Lodge at Killington Mountain (just a 10 minute walk or 2 minute shuttle ride to the slopes) and right next door to the Killington Golf Course. With our recently updated kitchen, renovated master bathroom, luxury vinyl flooring and new furniture, you are sure to enjoy our home away from home in the Green Mountains!

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.

Ski Back to Trail Creek!
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!

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!

Newly renovated ski retreat at Killington
Located at Mountain Green Resort, Building III. Walk to Snowshed Lodge to begin your day of skiing, or take the free shuttle that will pick you up outside the entrance. After your day of skiing ends and you return to the unit, to experience the many amenities that the resort has to offer: indoor pool, eucalyptus steam room, two spas, sauna, fitness center,. You may prefer to stay in the unit and watch skiers come down the mountain.

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.

Cozy 1BR, Shuttle/Walk to Lifts, Covered Parking
Our bright and cozy 1-bedroom condo in Building 3 at Mountain Green Resort is the perfect home base for your Killington getaway. Walk to Snowshed Base Lodge or hop on the winter shuttle that runs every 15 minutes. Enjoy a renovated kitchen, dedicated Wi-Fi, and smart TVs for easy streaming. Resort amenities include an indoor pool, hot tub, sauna, and gym year-round, plus an outdoor pool from Memorial Day through mid-September.

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!

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!

Secluded Luxury Lodge On Stratton w/ Heated Pool

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!

Historic 1850’s Renovated Farmhouse w/ Pool!
Apartment rentals with a pool

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

Serene 1-BR Ski-In/Ski-Out Retreat on Okemo Mtn.

SKI IN/OUT @ Mount Snow (Hot Tub & Pool)

1 BR Best Location w/ Pools/Massage Chair/Hottub!

Cozy Slopeside Studio at Pico

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

Cozy condo within walking distance to the slopes.

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

Ski-in/out Jackson Gore Studio w/Kitchen

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

The Woods Renovated 1BR Studio close to the slopes

Killington ski resort condo

Cozy Quechee Cabin near Woodstock and skiing

Dream Catcher Farm

Studio Condo: Shuttle. Close to Resort. Pool.

Cozy Mountain-style Condo by Okemo with a View!
When is the best time to visit Cavendish?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹22,547 | ₹27,437 | ₹20,736 | ₹21,189 | ₹22,547 | ₹20,736 | ₹22,547 | ₹23,000 | ₹22,547 | ₹23,181 | ₹24,177 | ₹26,531 |
| 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 Cavendish

Total holiday rentals
Explore 40 holiday rentals in Cavendish

Nightly prices starting at
Cavendish holiday rentals start at ₹10,866 per night before taxes and fees

Verified guest reviews
Over 960 verified reviews to help you choose

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

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Cavendish holiday rentals include wifi 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
- Killington Resort
- Pats Peak Ski Area
- Monadnock State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Mount Snow Ski Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Crotched Mountain Ski and Ride
- Montshire Museum of Science
- Mount Sunapee Resort
- Dartmouth College
- Mount Monadnock
- Southern Vermont Arts Center
- Warren Falls
- Quechee Gorge
- Camp Plymouth State Park




