
Holiday rentals with a pool in Trent Hills
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Trent Hills
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

Welcome to Paradise on Rice Lake 4-6 month winter
Welcome to Paradise on Rice Lake Unique, semi-detached cottage has a heated pool, southern exposure, private deck with glass railing overlooking the lake. Included: 3 beds total, King, Queen Murphy bed with Tempur-Pedic + pull out Queen sofa bed All S/S appliances, W&D, dishwasher, gas stove, firewood available $15, propane BBQ, outdoor dining area overlooking the lake. boat dock in front, great fishing, 5min to Keene for LCBO, Pharmacy, Gen Store, ATM, 1:20 from Toronto, :20 to Peterborough

Moon River
“Moon River, wider than a mile. I’m crossing you in style”. Located at a 5-star location, this historic home was freshly designed by a professional interior designer. The stunning emerald tiles in each bathroom reflect the color of the river running outside. While enjoying a warm bath in a freestanding bathtub in the bedroom, you’ll be amazed by the bright moon above the peaceful river outside the window. “Moon River” is ideal for a large family(up to 16) vacation or a romantic getaway for 2.

A "Peace" of Eden -- Private suite in country home
Quiet country setting surrounded by forest and farmland, bordering on the Altberg Wildlife Sanctuary Nature Reserve. Lower level suite with private entrance includes one separate bedroom, one bed with room divider in the common space, plus a full bath, kitchen facilities, and living area. Once called the "United Nations of birds", we are just a short drive from public beaches, lakes, the Victoria Rail Trail, and Monck's Landing Golf Course (stay and play package available). Fabulous star-gazing!

Beautiful Relaxing Getaway With Sauna&Private Pool
WOODLANDS If you are looking for total privacy in the heart of the County, you have found it! Woodlands offers you almost 4 acres of land, beautiful bungalow with 2000sq feet of living space upstairs, 2000sq feet of a walkout basement, and a large outdoor pool. Please inquire about pets prior to booking. Only non shedding dogs up to 40 lbs are allowed. Please note that the pet fee applies to each pet. We do not accept cats due to allergies.Thank you for your understanding STA LIC ST-022-0160

Belmont Lake Getaway
8 + acres w/ Fully Private separate entry facing pond & lake ,one bedroom with queen bed, living room with queen pull out couch , TV etc, dining room, full kitchen, and bathroom is wheelchair accessible, host main house above, Summer: kayaks and canoes , fishing, ducks & pond , full gardens. Pizza night is every Saturday . Winter: snow shoes skating, ice fishing ,curling ,lots of winter activities. Local Chocolate & Cheese factories, Wineries, We added an Eco Pool with beach for swimming.

Prince Edward Landing
Victorian Home in PEC gets a full renovation to become a one of a kind vacation home. Featured in the Globe & Mail the house is a 2018 restoration of old-world charms with as many contemporary comforts as one wishes. From the gorgeous landscape and a screened-in, white-trim front porch to the fully modern spectacular interior The back of the house is a stunning starkly contemporary black box, designed by architect Jay Pooley, a lecturer at the University of Toronto’s school of architecture.

Luxury, One-of-a-kind Pool and Zen with Horses
Luxury spaces for the whole family, YEAR ROUND Zen with horses in our heated barn, magnificent views. Private suite, Fire Pit, Hiking Trail, outdoor kitchen and BBQ. Billiards, shuffleboard, trampoline, table tennis, basketball and more. Book an archery tag or axe throwing game! Search horse experiences Sky Haven Equestrian in Bethany. Kids Stay Free! When booking enter number of adults only. Wutai Shan Bhuddist Garden is 4 min. away. Great for entertaining. Inquire about our event space.

A Modern Creekside Retreat in PEC (MT20211638)
Escape to the County Creek House, a 3,000 sq ft, 4-bedroom, 2.5-bathroom haven designed for unforgettable gatherings. This design-forward gem is surrounded by 6 acres of private land backing onto a serene creek and conservation area, offers the ultimate blend of modern luxury and natural beauty. Perfectly located in the heart of Prince Edward County (PEC), you’re just minutes from world-class vineyards, provincial parks, sandy beaches, and the gourmet and antique treasures of The County.

Lakefront Cottage with Pool, Hot Tub & Sauna
Welcome to your Prince Edward County getaway! Our Muskoka-style lakefront cottage with pool, sauna and hot tub was custom-built in 2004. Perfect for families and very private, it comfortably sleeps 8 adults with additional room for children (10 years and under). Located literally on the edge of Consecon Lake, we're 13 mins from Wellington & close to over a dozen wineries. We've been Superhosts since 2017, and our family would love to host you and welcome you to our little slice of paradise.

Cheerful 2 bedroom cottage with indoor fireplace.
Relax with the whole family at this peaceful rustic cottage that is situated on 21 acres with trails in the beautiful County of Trent Hills. Cottage is fully furnished with fully equipped kitchen with appliances, pots and pans, microwave, BBQ with patio table and chairs and gazebo. 3 piece bathroom. Wood stove inside for those chilly nights. Cottage has wifi. Large outdoor fire pit to be enjoyed in the evenings. Small above ground pool to cool off. Hot tub for you to relax and unwind.

Hidden Acres - a Stay and Play Retreat!
Are you looking for some nature therapy? You'll be nestled in several acres of forest, where you can hear the birds and enjoy the private backyard. The hot tub and campfire* beckon in all seasons, and the heated inground pool is open from mid-June to Labour Day each year. We are dog friendly, but cannot accept other pets due to allergies. Please be sure to read our house rules before booking. **We are excited to share that we now offer a Level 2 EV outlet!** Licence number STR2025-344

The Old Stone Farmhouse with Hot Tub & Heated Pool
Renovated historic stone farmhouse located about 6km from both Picton and Bloomfield. Relax in the hot tub, swim in the pool, lay in the hammock or enjoy a campfire under the stars. Over 2 acres of beautiful country views to explore. However, we are still close enough to the action that you can get to Bloomfield, Picton or some of the biggest wineries by bike. Ideal for couples and small group getaways. Hot tub is operational year round. Pool is open beginning of June - end of September.
Popular amenities for Trent Hills rentals with a pool
House rentals with a pool

Lakeside Retreat - Pool+GolfSim+HotTub+Sauna+Gym

Stone House Manor

Oriole Ridge Retreat, Hot Tub, King Suite

Bungalow Citron - Waterfront with Pool!

Luxury Farmhouse Retreat / Hot Tub / Games Room

Pearadise on West Lake | Waterfront w/ Pool

The Lakeview In PEC

Kawarthas storybook cottage, hot tub & heated pool
Other holiday rentals with a pool

The Carrying Place

Sandy Shore Cottages, Loft #7 (3 sing+doub+futon)

Apple Route Getaway!

Multi-Family cottage w/ Pool near Presqu'ile & PEC

Cozy Home, Outdoor Bar, Hot Tub, BBQ & Bonfire

Waterfront Sunrise bungalow with Swimming Pool

PEC Farmhouse w/ pool,basketball court,pizza oven

Fenelon Falls Condo Retreat on Cameron Lake
Quick stats about holiday rentals with a pool in Trent Hills
Total holiday rentals
Explore 30 holiday rentals in Trent Hills
Nightly prices starting at
Trent Hills holiday rentals start at € 68 per night before taxes and fees
Verified guest reviews
Over 450 verified reviews to help you choose
Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 of Trent Hills holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Trent Hills rentals
4.8 Average rating
Trent Hills stays are highly rated by guests – averaging 4.8 out of 5!
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- North Beach Provincial Park
- Presqu'ile Provincial Park
- Black Bear Ridge Golf Course
- Cobourg Beach
- Batawa Ski Hill
- Riverview Park and Zoo
- Black Diamond Golf Club
- Wildfire Golf Club
- Wolf Run Golf Club
- Kawartha Golf Club
- Kawartha Nordic Ski Club
- Grange of Prince Edward Vineyards and Estate Winery
- Traynor Family Vineyard
- Redtail Vineyards
- Closson Chase Vineyards
- Brimacombe
- Casa-Dea Winery & Banquet Hall
- Rosehall Run Vineyards Inc
- Hinterland Wine Company
- Timber Ridge Golf Course