
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.

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

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!

Classic VT Ski Chalet - Walkable to Okemo Ski Lift
PLEASE NOTE: No Saturday arrivals or departures, no pets, no parties Recommended local activities & floor plans of our home can be found on our OkemoHouse site Our "Trailside Chalet" is ON OKEMO MOUNTAIN, a 200 yard walk downhill from the Sunshine Chairlift & Suncatcher ski trail on Okemo's Southface (open end if Dec - late Mar). This Classic Vermont Ski Chalet features 5 bedrooms, sleeps 12, and is on a private wooded lot overlooking a babbling brook with seasonal fire-pit & charcoal grill.

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.

Hotel Chic - Home Comfort -Ski Easy.
HOTEL CHIC - SKI EASY ELEGANT - COZY - SPOTLESS ❄️Killington - 15 minutes ❄️Pico - 5 minutes ❄️WIFI❄️QUIET❄️FIREPLACE ❄️COMFY❄️IMMACULATE ❄️SUPERHOST RATED OUR ULTRA COZY RETREAT WAITS JUST FOR YOU ⛷️ 🏂Pico-5 minutes ⛷️ 🏂Killington-15 minutes 🥾Minutes from LT/AT 💍Wedding Venues 🚴Mtn Biking •Squeaky Clean •Fireplace, WIFI •TV in living room & bedroom •Private covered porch •Keypad check in •Smoke free/Pet free NOTE: Condo regs allow 2 adults(21 yrs). Can not accommodate children.

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

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

MtSnow/Stratton Ski Lodge-Hot Tub-Game Room-Pool

Hilltop 9-BR Mountain Retreat 5-min to Okemo

Adams Farm-"The Little Farmhouse"

The Brick House on Washington Street

Dana Road House Sunlit VT Country Home w/HotTub

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

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

Cozy Slopeside Studio at Pico

Killington Style Suite: Modern, Central Condo. 222

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

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

Elegant 3BR with Fireplace & Shuttle to Slopes

Serene Top Floor Condo (resort style amenities)

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

Stratton Mt Summer: Golf, tennis, hike, bike, swim

Cozy Mountain Condo - Ski In/Ski Out

Cozy Cabin - Lake, Ski, Golf!

Cozy, clean studio with picturesque Vermont views!

Charming Killington get away with pool, sleeps 4

Modern Cottage between Stratton and Mount Snow VT

Mount Snow direct access! Pool & hot tub! Ski

Ski Chalet-Style Home with Spa, Eastman Community
When is the best time to visit Cavendish?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | 
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$52,120 GYD | G$63,423 GYD | G$47,933 GYD | G$48,980 GYD | G$52,120 GYD | G$47,933 GYD | G$52,120 GYD | G$50,027 GYD | G$52,120 GYD | G$52,120 GYD | G$47,933 GYD | G$54,004 GYD | 
| 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 G$23,025 GYD 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! 
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Mount Pocono Vacation rentals
- Quebec City Vacation rentals
- The Hamptons Vacation rentals
- Family-friendly rentals Cavendish
- Rentals with a patio Cavendish
- Fitness-friendly rentals Cavendish
- Rentals with a fireplace Cavendish
- Rentals with a washer and dryer Cavendish
- House rentals Cavendish
- Rentals with a fire pit Cavendish
- Rentals with outdoor seating Cavendish
- Pet-friendly rentals Cavendish
- Cottage rentals Cavendish
- 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
