Vacation rentals with a pool in Woolwich

Guest suite in Elora-Salem

Private Basement Suite with Heated Pool Near Elora

Welcome to The Salem Hideaway, a private basement suite nestled among the trees in the quiet village of Salem, just minutes from historic Elora. Enjoy your own private entrance, heated pool, fire pit, and peaceful surroundings. We live upstairs, so you may occasionally hear normal household sounds, but we do our best to keep things quiet and ensure you have a relaxing stay. m Minutes from downtown Elora, you’ll be close to shops, restaurants, hiking trails, and everything the area has to offer

FamilyLocationHospitality

4.98 out of 5 average rating, 48 reviews

4.95 out of 5 average rating, 213 reviews

A welcoming porch features a blue exterior with white trim, adorned by potted plants and lush greenery. Rocking chairs are positioned on the porch, providing a comfortable space to relax. The pathway is lined with stones, leading from the driveway to the entrance.

Apartment in Ariss

Rural Retreat, near to Elora

A peaceful , rural, retreat in Ariss. Hot tub, great bird watching. Well situated between Elora, Fergus, St Jacobs and Guelph. Visit Cox Creek Winery, Kissing Bridge, G2G & Cotton Tail hiking/biking trail, snowshoeing, snowmobile trails & Chicopee Ski Resort. Two dogs on the property. Walkout basement, king bed, portable crib (on request) shower, kitchenette, seating area, natural light. Large backyard, firepit, barbeque, outdoor eating area. Keyless, separate, private entry, free parking.

LocationFamilyTV

4.88 out of 5 average rating, 132 reviews

A serene view of the villa is captured from the edge of the natural spring-fed pond, showcasing its spacious, multi-level design. Surrounding greenery, including trees and landscaped gardens, adds to the tranquility of the setting. Fluffy clouds drift across a bright blue sky.

Villa in Cambridge

Luxury Villa for Accommodation

★★★ SUPERHOST for 6+ years ★★★ Escape to this stunning, secluded villa for exquisite accommodation or hosting memorable events. ✔ Secluded villa on 8.8-acre lot ✔ Private 17 ft deep natural spring-fed pond + hot tub ✔ 4000 sqft living space ✔ Full access ✔ 4 bedrooms, 7 beds ✔ High-end finishes: Offers comfort & elegance. ✔ BBQ ✔ Next to Whistle Bear Golf Club & Langdon Hall (Relais & Châteaux, 5 Diamond dining), Cambridge Mill, walking trails, scenic Blair Creek. ✔ 401 easy access

FamilyValueHot tub

4.99 out of 5 average rating, 113 reviews

Apartment in Waterloo

Charming Hideaway: 1-bedroom Apartment

Whether you’re in town for sports, work, or family, you'll love how the apartment is: Fully Furnished: from kitchen to bedroom, we’ve got you covered. Cozy: Gas fireplace and a queen air mattress for extra guests. Private Entrance: Your own smart lock access. Outdoor Space: Your own private deck with a BBQ. Heated Pool: SHARED pool available mid May to September. Entertainment: Stay connected with WIFI and enjoy Netflix, Prime, and Disney on the Smart Parking: No worries about finding a spot

ValueFamilyAccuracy

4.87 out of 5 average rating, 111 reviews

A spacious living room is highlighted by tall wooden ceilings and large windows that invite ample natural light. Two comfortable sofas face each other over a coffee table, with a patterned area rug underfoot. A small fireplace and colorful stained glass add character to the warm design.

Barn in Milton

Five Star Hayloft Suite

This open space home is in the top level of a century-old bank barn. Witness the beautiful architecture while enjoying modern amenities like an open-concept kitchen, projector & movie lounge, and more! Enjoy 180 degree views from the bay window in the living room during your stay. Five Star Ranch offers a year-round getaway in a beautiful country setting. Situated on a working farm, and surrounded by gardens, animals and beautiful forest, it is a perfect destination for seclusion and peace.

LocationFamilyGrill

4.97 out of 5 average rating, 35 reviews

A vibrant, triangular-shaped house is surrounded by greenery, reflecting in a clear, inviting swimming pool. A shaded seating area with lounge chairs can be seen beside the pool, and large glass doors allow natural light to fill the interior space.

Home in Elora-Salem

Riverside Retreat w Hot Tub, Pool & Sauna in Elora

Are you looking for a Fall Getaway in Elora? Althea Crystal Retreat, located in picturesque Elora, Ontario, has everything you need. For this September 2026: Get 4 nights at 20% off Unwind in one of our unique crystal rooms. Relax by the hot tub, and warm up in the sauna and by the indoor or outdoor fireplace. Go swimming in the beautiful heated pool (closes end of September). Get cozy by our fireplace while you watch TV. Look out to the breathtaking views of the river nearby.

FamilyLocationComfort

Guest suite in Orangeville

Private Hot Tub & Pool - Headwaters Retreat

Escape to our modern and rustic Queen Suite, with private hot tub right at your door. Relax by the pool, or unwind by the fireplace & enjoy Netflix & Amazon TV. This cozy retreat features a private entrance, ensuite bathroom, and a second bedroom with twin beds. Steps from scenic hiking trails, minutes from the town center, your stay is ideal for outdoor adventures, wine tours, weddings, work trips or a quiet escape away. Book now for your ultimate getaway in comfort and nature!

ValueLocationHot tub

4.92 out of 5 average rating, 890 reviews

5.0 out of 5 average rating, 28 reviews

A spacious outdoor area features a heated pool surrounded by a tiled deck. Comfortable seating is arranged under large umbrellas, alongside a dining set and a barbecue grill. Lush greenery and potted plants enhance the relaxing atmosphere of the space.

Home in Cambridge

Under the Whispering Pines

Escape from the noise of the city and relax at our charming, home-away-from home. We are located in Blair (minutes from the 401, Langdon Hall, Roseville Estates, WhistleBear Golf Course and the Gaslight District; just to name a few). You can relax in the beautiful heated pool and welcome to enjoy any of the other outdoor spaces. At night you can cozy up by either of the wood-burning fireplaces, watch tv, listen to music or just chill. Coach House also included in price.

FamilyLocationCondition

4.97 out of 5 average rating, 147 reviews

Guest suite in Kitchener

The Oasis

Enjoy the bright, spacious, and homey cottage vibes with a fully private saltwater pool, hot tub, luscious green yard, fire pit area, and several walking trails out the back gate. Retreat to the spacious walk out basement suite with 70” TV home theater, elliptical trainer, desk space and plenty of windows open to the forest view behind the house. Beautiful Doon neighbourhood within minutes of the 401. Plenty of shopping and eating choices within a few minutes drive.

ValueLocationWifi

4.96 out of 5 average rating, 130 reviews

The exterior of a two-story house showcases a blend of stone and dark wood siding, with a spacious deck accessible from the upper floor. Lush green grass and neatly arranged flower beds surround the home, while a gray sky sets a calm backdrop.

Home in Alton

Cozy Country Spring Getaway | HotTub + Fire Pit

Escape to the countryside this spring 🌸 Unwind in the hot tub or pool, enjoy cozy fires under the stars, and soak in the peaceful charm of Alton. Perfect for a relaxing getaway, girls weekend, or quiet work-from-home retreat. • Sleeps up to 8 guests comfortably • 3 cozy bedrooms (2 with private decks!) • 1.5 bathrooms • Fully equipped kitchen + BBQ patio for year-round grilling • Stylish living room with fireplace & smart TV • Fast Wi-Fi, workspace-friendly

FamilyValueCheck-in

4.97 out of 5 average rating, 225 reviews

Guesthouse in Breslau

House on the Hill

What makes The House unique? How about: - a year-round heated indoor pool & sauna - private 2-bedroom + loft guesthouse with private entrance - fully-equipped kitchen - homey living area with electric fireplace - 27 gorgeous acres with 2 ponds - private patio & BBQ There's so much more! Come join your hosts Frances & Rod and experience a country retreat in the middle of the city... all this within 5km to Waterloo Int'nl Airport & 15 min to tri-cities & 401.

FamilyLocationDecor

4.75 out of 5 average rating, 117 reviews

A comfortable sleeping area is furnished with a queen bed, dressed in a patterned blue and white blanket. A cozy sofa is positioned nearby. Warm lighting is provided by a wall-mounted fixture, and a piece of artwork featuring a tree is displayed above the bed.

Home in Milton

Spacious, Pet Friendly Basement Apartment

Quiet, pet-friendly private basement suite designed for comfort and easy stays. Features a queen bed, sofa bed, fully equipped kitchen, dining area, in-suite laundry, free Wi-Fi, and complimentary coffee & tea. Guests enjoy a shared backyard with a seasonal pool and barbecue in summer. Loved for its privacy and comfort while being steps from a park, grocery store, pharmacy, bank, and nearby restaurants—perfect for short or extended stays.

ValueFamilyDecor

Popular amenities for Woolwich rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.93 out of 5 average rating, 81 reviews

A spacious living area features a stone fireplace with a wooden mantel as its focal point. Comfortable seating, including a sectional sofa and armchairs, surrounds a glass coffee table. Natural light filters through large windows, complemented by warm wooden accents on the ceiling.

Home in Kitchener

Chalet by hiking trail and ski hill

LocationFamilyCheckout

4.75 out of 5 average rating, 32 reviews

Home in Erin

Indoor Pool • Hot Tub • Heated Dome • 40 min GTA

LocationFamilyQuiet

5.0 out of 5 average rating, 15 reviews

Home in Hamilton

City Meets Forest Year Round Tree House Retreat

LocationFamilyDecor

4.95 out of 5 average rating, 22 reviews

Home in Cheltenham

Indoor Pool & Hot Tub Villa | Sleeps 14

FamilyLocationOutdoor spaces

4.86 out of 5 average rating, 14 reviews

Home in Burlington

3 bedroom home close to downtown with Pool!

FamilyLocationComfort

4.91 out of 5 average rating, 81 reviews

A private backyard is showcased, featuring a heated saltwater pool with inviting blue water. A shaded seating area is set under a large umbrella, surrounded by lush greenery and vibrant yellow flowers. The exterior wall of the home is adorned with light-colored siding, complementing the tranquil setting.

Home in Hamilton

The Bayfront - Harbour Views + Private Pool!

ValueFamilyLaundry

4.96 out of 5 average rating, 25 reviews

An outdoor pool area features a sparkling blue pool surrounded by a sun-drenched patio. Lounge chairs with colorful cushions are positioned along the edge, and a shaded umbrella offers respite from the sun. Lush greenery lines the space, providing a serene backdrop.

Home in Brantford

Brant Paradise. Where luxury meets country charm.

LocationFamilyAmenities

4.92 out of 5 average rating, 102 reviews

The entrance of a renovated stone home is framed by lush greenery and colorful flower beds. A wide, paved pathway leads to the front door, flanked by stone steps, while large windows allow natural light to fill the interior, showcasing the property's unique architectural features.

Home in Elora-Salem

Estate, Secluded On the Grand River.

ValueLocationBathroom

Condo rentals with a pool

5.0 out of 5 average rating, 34 reviews

Modern High-Rise Condo w City Views & Balcony

LocationValueCheck-in

A modern living area showcases a dark sectional sofa, complemented by a round coffee table atop a light rug. Large glass doors provide access to a balcony, while a television stands on a white media console adorned with decorative items and potted plants.

4.88 out of 5 average rating, 43 reviews

Lux Condo by Downtown Kitchener

LocationValueComfort

4.88 out of 5 average rating, 42 reviews

A stylish living area is presented with a green sofa and two textured chairs surrounding a light wood coffee table. A large television is mounted on the wall, and vibrant tropical wallpaper adds a splash of color. Ample natural light enters through two large windows.

Condo in Waterloo

The Laundry Rooms, Waterloo - Two Bedroom Suite

LocationFamilyView

A modern living area features a cozy armchair and a small dining table beside large glass doors that lead to a balcony. Natural light fills the space, highlighting the subtle color palette. A flat-screen TV is mounted on the wall, and greenery adds a touch of freshness.

4.88 out of 5 average rating, 34 reviews

City Views & Private Balcony | Gym, Pool & More!

LocationValueHospitality

4.85 out of 5 average rating, 34 reviews

LuxCondo in the downtown kitchener uptown waterloo

LocationFamilyComfort

4.75 out of 5 average rating, 12 reviews

City Views | Pool, Gym, Bowling, Games Room & More

LocationHot tubQuiet

4.69 out of 5 average rating, 59 reviews

Luxe Suite With Home Cinema - Gym, Bowling, Pool

FamilyLocationWalkability

A modern open-concept space features a well-equipped kitchen on the left and a cozy seating area with a sofa and television. Large glass doors lead to a private balcony, allowing natural light to fill the room. Light wood flooring adds warmth to the environment.

4.7 out of 5 average rating, 47 reviews

*Modern* 1 Bed Condo Station Park

ValueLocationHot tub

Other vacation rentals with a pool

Farm stay in Guelph/Eramosa

A stone farmhouse is set against a clear blue sky, with a saltwater pool in the foreground. The pool area is bordered by lush greenery and features lounge chairs arranged on a flagstone patio. The reflection of the house is visible on the pool's surface.

Luxe B&B - Pool, Firepit, Hot Tub & Farm Animals

LocationValueCheck-in

4.98 out of 5 average rating, 83 reviews

4.85 out of 5 average rating, 41 reviews

A private pool is framed by a spacious patio and surrounded by well-maintained greenery. The villa stands nearby, featuring large windows that overlook the serene outdoor area. A natural stone sits on the patio, adding to the tranquil ambiance.

Guesthouse in Fergus

Country Villa Fergus Elora

LocationValueAccess

4.89 out of 5 average rating, 9 reviews

Apartment in Kitchener

City Views at Station Park + Swim Spa + Hot Tub

LocationFamilyCleanliness

4.97 out of 5 average rating, 36 reviews

The historic farmhouse is set against a backdrop of lush greenery and flowering plants. The white exterior features traditional architecture, including multiple windows and a gabled roof. A vibrant sky with scattered clouds complements the serene outdoor setting.

Farm stay in Milton

Rustic Farmhouse w/ pool, tennis court on 100 Acre

ValueLocationPets

5.0 out of 5 average rating, 11 reviews

Guesthouse in Cambridge

Historic Blair Road Coach House and Terrace Suite

ValueFamilyHot tub

4.87 out of 5 average rating, 95 reviews

A modern living area features a white media console with a speaker and decorative elements, accompanied by a flat-screen TV displaying the word 'WELCOME.' Natural light enhances the space, while a potted plant is nestled in a woven basket beside the console.

Apartment in Kitchener

21st- floor Luxury & City Views

LocationValueWalkability

Farm stay in East Garafraxa

An open concept living area features high, vaulted ceilings with wooden beams, warmly lit by recessed lighting. Comfortable leather seating is arranged around a large wooden table. Floor-to-ceiling windows provide a panoramic view of the surrounding landscape, enhancing natural light throughout the space.

Country Log Home On 100 Acre Ranch

FamilyValueBathroom

4.94 out of 5 average rating, 35 reviews