
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!

Comfy ski in/out studio at base of Pico-Killington
Studio at the base of Pico with a balcony. Free shuttle service from my place to Killington, which is 10 minutes away.Brand new sofa bed with a pillow top. Room divider. Lots of TV channels with Xfinity. Luggage cart and elevator for easy access. Fast Wi-Fi. Free ski locker with one key for each guest. There is a laundry room with coin operated machines. The kitchen is fully equipped. Towels, soap, shampoo and conditioner provided for one day. No daily cleaning service. No parties. Free parking

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna
Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

Historic Home on 17 acres of land. Go escape!
This place is a dream. Please enjoy the outdoors and everything this amazing place has to offer. The pool will be reopened around May 2025 (weather dependent. It is a heated pool and salt water. Pool rules: absolutely no diving. No children under the age of 18 should be near or in the pool area without supervision under any circumstances. NO glassware by the pool. If there is an incident with glass near the pool area please tell our property manager immediately. If you need anything ask!

Vermont Chalet w/ Indoor Hot Tub 10Min to Stratton
Situated at the edge of protected forest land,this stay is a match for those who are seeking privacy to get away from the chaos of urban life and to decompress.How ? Enjoy the private and heated pool(until Sep15) during the day,and hang out by the outdoor fire pit when the sun is setting,and finish your evening off at the enclosed and brand new sea-salt hot tub!You will smell changes in the air as you drive through the trees,and you will hear the birds instead of the sirens when you are here.

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 | AC | Sauna| Fireplace
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!

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

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.

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails
Experience year-round adventure at Sunrise Village at Killington, just steps from scenic trails and the Sunrise Village Triple Lift (488 ft away). After a day of outdoor fun, unwind by the cozy gas fireplace. Explore nearby hiking, mountain biking, kayaking, and golfing. The indoor sports complex—featuring a pool, hot tub, and gym—is a short walk away. Perfect for outdoor lovers looking to relax and make unforgettable memories!

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!

One Bedroom Suite Near Okemo
This 675 square foot suite features a master bedroom with king bed and flat screen TV, separate living room with queen sleeper sofa, flat screen TV, and gas fireplace, full size kitchen, dining area, washer & dryer, and private bath with jetted tub. The Suites location in the Pointe hotel gives you access to the indoor pool, hot tub, fitness room and game room.
Popular amenities for Cavendish rentals with a pool
House rentals with a pool

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

Lake Pinneo, Golf View, Hot Tub - Tee Time Retreat

Hilltop 9-BR Mountain Retreat 5-min to Okemo

Adams Farm-"The Little Farmhouse"

The Brick House on Washington Street

Premier Quechee Newton Village Condo: Pet Friendly

Dana Road House Sunlit VT Country Home w/HotTub

Peaceful condo at Okemo - Direct Ski Access
Condo rentals with a pool

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

Winter Dream! The Handle Lodge at Snowtree Condos

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

Cozy Slopeside Studio at Pico

Killington Style Suite: Modern, Central Condo. 222

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

Elegant 3BR with Fireplace & Shuttle to Slopes

Cozy condo within walking distance to the slopes.
Other vacation rentals with a pool

Cozy Mountain Condo - Ski In/Ski Out

Cozy Cabin - Lake, Ski, Golf!

Ski in Cozy 2 Bedroom only 1/2 mile to Mtn & Apres

Condo w/ great amenities 4-seasons! Ski in Ski out

Cozy, clean studio with picturesque Vermont views!

Beautiful Lakeside home Eastman Lake; ski nearby

New Resort Condo Close to Lifts

Stratton Duplex Condo Steps to Lifts, Village!
When is the best time to visit Cavendish?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $348 CAD | $424 CAD | $320 CAD | $327 CAD | $348 CAD | $320 CAD | $348 CAD | $334 CAD | $348 CAD | $348 CAD | $320 CAD | $361 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 $154 CAD 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 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! 
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- House rentals Cavendish
- Rentals with a firepit Cavendish
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- Pet-friendly rentals Cavendish
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- Rentals with a hot tub Cavendish
- Condo rentals Cavendish
- Rentals with pools Windsor County
- Rentals with pools Vermont
- Rentals with pools United States
- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Mount Snow Ski Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Dorset Field Club
- The Shattuck Golf Club
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Hooper Golf Course
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Whaleback Mountain
- Northeast Slopes Ski Tow
- Brattleboro Ski Hill
- Ekwanok Country Club
