
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

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”.

SKI ON/OFF Spruce Glen C | Sauna| Fireplace | AC
Come and enjoy the largest private trailside property in Killington (almost 4 acres), with more convenience and value than large house rentals and more privacy than condo villages. The direct ski on/off is the easiest you'll find in Killington. Quiet and serene, the mature New England Evergreens and gentle mountain stream are a tranquil relief. An ideal ski in ski out or any season vacation getaway. Great Eastern is the longest green run in the East. Welcome to Spruce Glen!

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!

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

Dana Road House Sunlit VT Country Home w/HotTub

Premier Quechee Newton Village Condo: Pet Friendly

Historic Home on 17 acres of land. Go escape!
Condo rentals with a pool

Right at Killington !

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

Winter Dream! The Handle Lodge at Snowtree Condos

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

Cozy Slopeside Studio at Pico

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

Cozy Studio Condo on Bus Rte to Killington Resort!

Walk to Mt. Snow-Spa-Summer Pool
Other vacation rentals with a pool

Stratton Long Trail House: Quick Walk to Lifts!

No Cleaning Fee~10% OFF~Walk To Mountain~Amenities

Boutique Studio Base Camp: Shuttle, Pool, EV, New

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

Cozy Quechee Cabin near Woodstock and skiing

Dream Catcher Farm

Cozy Mountain-style Condo by Okemo with a View!

Luxurious family retreat home in the mountains
When is the best time to visit Cavendish?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $340 CAD | $414 CAD | $313 CAD | $320 CAD | $340 CAD | $313 CAD | $340 CAD | $347 CAD | $340 CAD | $350 CAD | $365 CAD | $401 CAD |
| 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 $164 CAD per night before taxes and fees

Verified guest reviews
Over 960 verified reviews to help you choose

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

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Cavendish vacation 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!
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Long Island Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Québec City Vacation rentals
- Rentals with a washer and dryer Cavendish
- Condo rentals Cavendish
- Rentals with a patio Cavendish
- House rentals Cavendish
- Fitness-friendly rentals Cavendish
- Cottage rentals Cavendish
- Rentals with a fireplace Cavendish
- Family-friendly rentals Cavendish
- Rentals with outdoor seating Cavendish
- Rentals with a hot tub Cavendish
- Pet-friendly rentals Cavendish
- Rentals with a firepit Cavendish
- 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
- Camp Plymouth State Park
- Quechee Gorge




