
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

Topridge 3BR w Incredible View & Private Hot Tub!
Oso Dream provides AMAZING panoramic views of Bear Mountain. Step out the front door and ski down Sundog trail to Sunrise Village Triple or step out the back door and hop onto Bear Cub trail to access Bear Mountain! Enjoy the amenities within the complex including indoor & outdoor heated pool (seasonal), sauna and gym. Guests also have access to the outdoor skating rink and xc ski trails (weather permitting). Free use of ice skates, puff hockey equipment, snow shoes, xc skies, poles and sleds!

Adams Farm-"The Little Farmhouse"
A Clean Ranch style home with hardwood floors located on a 100-acre Historic Vermont Farm. Retired farmers live in separate farmhouse & are available throughout your stay. Conveniently located just minutes away from MT Snow Ski Resort, Hermitage Resort, Stratton Mt. for Skiing, Snowboarding, Tubing, Hiking & Mountain Biking. 3 miles from downtown Wilmington. Minutes to public beaches and lakes. Use our trails for snowshoeing, X-Country Skiing or hiking. Our Pool is avail July -Labor day

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”.

The Brick House on Washington Street
Three guest bedrooms in a Colonial home on Washington Street make a great launchpad for visitors to Keene. From here, it's a pleasant walk or drive to Downtown restaurants, the theatre and shops. The Sterling family has owned this pretty place since 1982 and a design studio operates in the barn portion of the space. The open living room with TV and original fireplace adjoin a "tea room" with a bright bay window. Family chef-approved, guests are welcome to use the spacious kitchen.

⭐️Cozy Ski On-Ski Off Wood Fire Place & King Bed
Ski On-Ski Off cozy mountain condo with Real Wood Fire Place and King Size Bed in Sunrise Village on Killington Mountain. Updates include all new furniture in the Master Bedroom & Guest Bedroom, all new top of the line Stainless Steel Appliances in the gourmet kitchen, Tastefully decorated Living Room with new queen size sleep sofa & matching chairs. Simply walk to the end of the parking lot to the Ski On/Off trail. I own the adjoining unit -more info below.

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

Steps to Golf!
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!

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.

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis
Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer.

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!

Mt Snow Chalet: Peaceful Escape w/Hot Tub
Escape to the serene beauty of Vermont's Green Mountains at the Mount Snow Chalet, a charming retreat nestled on a private wooded lot in the desirable Chimney Hill community of Wilmington. 🏠🌳 Just minutes from the slopes of Mount Snow, our chalet offers the perfect blend of rustic charm and modern amenities for an unforgettable getaway. Designed with love and care, we invite you to relax and stay awhile! 🥰
Popular amenities for Cavendish rentals with a pool
House rentals with a pool

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

Updated Lake Cottage; 2 Min Walk to Lake

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

Classic VT Ski Chalet - Walkable to Okemo Ski Lift

The Fairway House - Premier Golf Course 3 BR Home

Lodge on the Loop: pet-friendly, hot tub & sauna

Idyllic Dorset Home: Serene Escape w/amazing views

Premier Quechee Newton Village Condo: Pet Friendly
Condo rentals with a pool

105 Fox Hollow Village Pvt - Red Fox - Unit B-4

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

~10% OFF~Walk To Mountain~Amenities

Cozy Mountain Retreat w Views | Pool, Hot Tub, Ski

Winterplace - Steps away from Slopes

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

Still skiing Deal Cozy 2 Bedroom .2 mi to lift

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

Sweet Retreat

Cozy Cabin - Lake, Ski, Golf!

A Chalet 4 All Seasons

Mount Snow Best View - Sauna|HotTub|Pool|Fireplace

Cozy Mountain-style Condo by Okemo with a View!

Cozy Studio Apartment

Jack Taylor Farm (with Alpacas & Inground Pool!)

Honeycrisp Cabin
When is the best time to visit Cavendish?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,190 | ﺩ.ﺇ1,186 | ﺩ.ﺇ1,161 | ﺩ.ﺇ859 | ﺩ.ﺇ914 | ﺩ.ﺇ841 | ﺩ.ﺇ914 | ﺩ.ﺇ933 | ﺩ.ﺇ914 | ﺩ.ﺇ940 | ﺩ.ﺇ981 | ﺩ.ﺇ1,076 |
| 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 30 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 980 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
30 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
- Tuckahoe 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
- Pet-friendly rentals Cavendish
- House rentals Cavendish
- Fitness-friendly rentals Cavendish
- Family-friendly rentals Cavendish
- Rentals with outdoor seating Cavendish
- Cottage rentals Cavendish
- Rentals with a patio Cavendish
- Rentals with a fireplace Cavendish
- Condo rentals Cavendish
- Rentals with a hot tub Cavendish
- Rentals with a fire pit Cavendish
- Rentals with a washer and dryer 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
- Stratton Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Pico Mountain Ski Resort
- Tenney Mountain Resort
- Fort Ticonderoga
- Ragged Mountain Resort
- Fox Run Golf Club
- Hildene, The Lincoln Family Home
- Dartmouth College
- Bromley Mountain Ski Resort
- Montshire Museum of Science
- Mount Sunapee Resort
- Emerald Lake State Park
- Southern Vermont Arts Center
- Warren Falls
- Mount Monadnock
- Camp Plymouth State Park
- Quechee Gorge





