Family-friendly vacation rentals in Woodstock

5.0 out of 5 average rating, 121 reviews

A vintage schoolhouse stands in the background, showcasing its distinctive architecture and large windows. In the foreground, a well-crafted bike rack holds several bicycles under a shaded canopy, surrounded by autumn foliage and a gravel pathway.

Home in New Hamburg

The Heart of New Hamburg - Picturesque Modern Home

This newly renovated schoolhouse doubles as a picturesque live-in museum! Well lit with stately windows, the upper level delivers a fusion of classic and modern with a fully equipped kitchen, master bedroom and large bathroom with a quaint tub and hand crafted fittings. The lower level boasts of 2 bedrooms with bathrooms, a cozy living area, kitchenette, dedicated workspace and separate entrance. The back patio has heated flooring; making the winter months bearable for outdoor activities.

FamilyKitchenTV

Guest suite in East Zorra-Tavistock

A cozy living area features a gray sofa facing a stone fireplace. A wooden coffee table sits atop a patterned rug, surrounded by two black chairs. Warm lighting creates a welcoming ambiance, complemented by wooden flooring and light walls.

Quaint Rural 2-Bedroom Oasis

The whole group will be comfortable in this spacious and unique property. Located between Woodstock and Stratford, very private with 1900 sqft of stylish decor and complete with a kitchen, living space and a games room. Terra Nova Nordic Spa is located directly beside rental. At evening, you can enjoy a campfire outside with lots of seating area and a private patio. Also available outside is a large hot tub with condition’s. We are a 2 night stay If considering a 1 night stay See other details

KitchenFamilyHot tub

4.93 out of 5 average rating, 108 reviews

4.88 out of 5 average rating, 137 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

FamilyKitchenCheck-in

4.84 out of 5 average rating, 166 reviews

A cozy sleeping area is featured with a spacious bed adorned with white linens and a patterned quilt. Soft string lights are gently draped along the wooden walls, providing a warm glow, while a window offers views of the surrounding greenery.

Cabin in Port Dover

Romantic Cabin For Two Or A Multi Family Stay

Cozy cabin for two + kids and pets. New this year is a second cabin which acts as extra sleeping space for a larger family or a second family. The second cabin would not be rented to strangers to those renting the main cabin. New this year, a third building which will have outdoor movie nights with kettle popcorn over an open fire. I will also be building a pizza fire oven. Play area for the kids and a large park across the dirt road for your enjoyment. Beach is a 15min walk as most amenities.

Indoor spacesKitchenCleanliness

4.99 out of 5 average rating, 165 reviews

Tiny home in Wellesley

RUSTlC~OFFGRlD~OASlS&MlCRO-CABlN

Are you looking for a space to get away, a peaceful oasis immersed in nature? Welcome to Clemmer's Chaos Rustic Escape! It's off-grid. No electricity. No running water. No Wi-Fi. There are bugs and critters. An outhouse for your business. A Cabin for two. A Space for Tents. A mini lake. You can swim, fish, kayak. There is a campfire pit, to cook over, sing around, or listen to the soft sounds of nature and crackling fire as you stare up at the stars. This is an experience. Au Naturel. You in?

FamilyIndoor spacesPets

4.97 out of 5 average rating, 117 reviews

A cozy seating area features a sleek gray couch adorned with black velvet pillows. A stylish lamp stands beside the couch, casting a warm glow. A piece of artwork depicting a cityscape is showcased on the wall, complementing the modern aesthetic.

Home in Stratford

4-Bedroom House,1 block from Lake

**BOOKMARK url: https://airbnb.ca/h/LindaStratford Licensed operation by the City (#2024-001); 4-bedroom 3-bathroom single detached brick house; Completely renovated, 2200 sqft modern vibe ; Spacious living space on main floor; Full-equipped kitchen and main floor laundry; 4 pristine bedrooms on second floor; Chic kids' game area on the loft; Large porch and rear patio; Prime location on the esteemed Elizabeth St, just one block from the Lake; Walking distance to theatres and downtown core;

KitchenFamilyOutdoor spaces

5.0 out of 5 average rating, 159 reviews

Cottage in Stratford

Holiday Getaway | 7mns to Dntwn | Games | Sleeps 8

Beautifully renovated 1200 sq ft farmhouse just 7 minutes from downtown Stratford — perfect for theatre trips, family getaways, and weekends with friends. Sleeps up to 8 guests with 2 king beds, 1 queen, and a pop-up sofa bed. Enjoy bright gathering spaces, games, patio dining, and cozy evenings after exploring Stratford’s theatres, cafés, shops, and restaurants. For select stays, guests may enjoy a complimentary local welcome treat featuring bakery items, wine, or other local favourites.

KitchenFamilyQuiet

4.96 out of 5 average rating, 344 reviews

A comfortable sleeping area features a spacious bed dressed in a patterned white and gray quilt. A microwave is placed nearby, along with a decorative screen partition. The bathroom area is visible in the background, showcasing essential amenities.

Apartment in Thamesford

Stay Inn Thamesford - Cozy 1 Bedroom unit/apt.

Enjoy a relaxing stay in our stylish and cozy little nook right in the hub of our friendly little town. Walking distance to Tim Horton's, RBC bank, variety stores, pizza pick up, town swimming pool, cannabis store and liquor & beer . Only 20 minutes London or Woodstock . It's important to note that our quaint unit does have a saniflo toilet and pumping system(ie. maceration system) which means there is noise associated with flushing and drainage. Please inquire if more info is needed!!

FamilyIndoor spacesDecor

Guesthouse in Springfield

A rustic wooden bunkie is situated in a spacious outdoor area, accompanied by a well-maintained garden and patio. Two lounge chairs are positioned outside for relaxation. A smooth concrete pathway leads to the entrance, enhancing accessibility and outdoor enjoyment.

Welcome to Brown's Rustic Country Bunkie

We invite you to enjoy our beautiful country rustic wooden bunkie. Sit outside and enjoy watching the animals or star gaze while having a campfire. Warm up after on the love seat while in front of the fireplace. A/C keeps you comfortable in the summer. This queen sized bed is fantastic to enjoying the free Wifi and Firestick TV. A great spot for a weekend get away. Golf at Tarandowah, Tamarack & Pineknot 10minutes Wave Nordic Spa is 15min Port Stanley/Port Bruce/Port Burwell 30-35min

FamilyKitchenAccuracy

4.85 out of 5 average rating, 178 reviews

4.78 out of 5 average rating, 177 reviews

Home in Simcoe

Oliver's Tiny Home In The Forest | Sauna & Hot Tub

Escape to the heart of a Carolinian forest in Simcoe, Norfolk County — a private tree farm sanctuary designed for those who crave stillness. Sink into the hot tub, warm your soul in the wood-burning sauna, or brave the cold plunge bucket on warm days. Surrounded by towering trees and birdsong, this cozy retreat welcomes couples, friends, and solo adventurers year-round. Don't see your preferred date available? Send us a message and we will add you to the waitlist.

KitchenFamilyCleanliness

4.97 out of 5 average rating, 228 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.

KitchenIndoor spacesRiver

4.88 out of 5 average rating, 118 reviews

A modern kitchen and dining area features sleek white cabinetry and stainless steel appliances. A central island with seating is complemented by a geometric light fixture above. Natural light streams in from a skylight, illuminating the open layout that connects to a cozy living space.

Apartment in Stratford

Bradshaw Lofts: The Penthouse

Experience luxury in Stratford’s historic Bradshaw Lofts. This penthouse suite offers two king bedrooms, two full bathrooms (one ensuite), in-suite laundry, and a skylight that bathes the space in natural light. Steps to the Avon Theatre, Stratford Festival stages, and top dining, cafés, and boutiques. A perfect heritage suite for couples, families, or friends seeking comfort, culture, and style in Ontario’s premier Shakespearean arts destination.

KitchenFamilyCheckout

Popular amenities for Woodstock family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.96 out of 5 average rating, 119 reviews

A spacious living area features a dark sectional sofa with decorative pillows, complemented by a wooden coffee table. A light blue area rug covers the floor, and wall art decorates the walls, creating a relaxed atmosphere. Natural light is provided by recessed lighting.

Home in Oakland

Luxury Oasis with Hot Tub/Pool

KitchenIndoor spacesValue

4.91 out of 5 average rating, 226 reviews

An inviting studio suite is furnished with a queen-sized Endy bed, flanked by two stylish armchairs. A small coffee table is placed beside the bed. A modern fireplace and a mounted television are positioned on the wall opposite the bed, creating a cozy atmosphere.

Guesthouse in Stratford

Brand new studio suite

FamilyKitchenLayout

4.86 out of 5 average rating, 145 reviews

An indoor heated saltwater pool is featured in a bright room with natural light streaming through skylights. The pool's clear water reflects playful patterns on the ceiling. Comfortable seating, including a hammock and lounge chairs, is arranged around the pool area.

Home in Aylmer

Indoor pool, hottub & video game room, near beach

FamilyKitchenComfort

4.93 out of 5 average rating, 124 reviews

A spacious living area features a vaulted cedar ship lap ceiling, with natural light streaming through large windows. A plush sofa is arranged around a wooden coffee table, and a decorative chandelier hangs above. A wall-mounted television and potted plants add to the home's inviting ambiance.

Home in Tillsonburg

Country settings

KitchenFamilyGrill

4.89 out of 5 average rating, 229 reviews

A serene bedroom is presented with a queen bed adorned in nature-themed bedding. A large mirror stands beside the bed, reflecting soft natural light from the window featuring light curtains. A wall art piece depicting a forest landscape enhances the calming ambiance.

Guesthouse in London

Charming Guesthouse Nestled Away

Indoor spacesFamilyQuiet

4.96 out of 5 average rating, 155 reviews

Guest suite in Kitchener

The Oasis

KitchenFamilyAccuracy

4.94 out of 5 average rating, 231 reviews

Farm stay in Eden

The Bunkhouse @ Stone Gate Farm & Sculpture Park

KitchenIndoor spacesBathroom

4.89 out of 5 average rating, 200 reviews

The open living area features a spacious grey sectional sofa with a round coffee table, surrounded by soft area rugs. Natural light flows through the windows, highlighting the neutral-colored walls. A dining area, visible in the background, includes a wooden table and chairs.

Home in Stratford

The Birmingham House

FamilyIndoor spacesQuiet

Family- and pet-friendly home rentals

4.99 out of 5 average rating, 210 reviews

A unique double A-frame house is framed by lush greenery, with a spacious driveway leading to the entrance. The structure features a combination of wood and stone elements, while flower beds with emerging blooms add color to the natural surroundings.

Cottage in St. Jacobs

St. Jacobs Triangle House - Countryside Escape

Indoor spacesKitchenHot tub

4.93 out of 5 average rating, 364 reviews

A modern dining area features a wooden table set for a meal, surrounded by light-colored chairs. A large window on the wall allows natural light to brighten the space, showcasing a view of greenery. The adjoining kitchen is visible in the background.

Home in Brant

The Walnut - Steps to Canoe Launch & Downtown

FamilyIndoor spacesAccuracy

4.92 out of 5 average rating, 231 reviews

A cozy living area is presented with a spacious sectional sofa, complemented by a side chair and a wooden coffee table. Minimalist decor includes potted plants and simple wall art on a shelf. Natural light enters through large windows, dressed with soft curtains.

Bungalow in St. Marys

The Old Blue Cottage of St. Marys

KitchenIndoor spacesPets

Shipping container in Simcoe

A repurposed shipping container is set within a forested area, surrounded by tall trees. A circular fire pit made of smooth stones can be seen in the foreground, with a fire crackling. A hammock is hung between two trees nearby, and two chairs are positioned on a wooden deck.

Little Can in the Pines - Bunkie No. 1

Indoor spacesFamilyNearby

4.97 out of 5 average rating, 155 reviews

4.92 out of 5 average rating, 230 reviews

Two brown horses are depicted in a snow-covered outdoor setting, closely positioned with their noses touching. Flakes of snow gently fall around them, creating a serene winter scene, while a house and snow-covered trees are subtly blurred in the background.

Bungalow in Hamilton

Horse Ranch with Hot tub

Indoor spacesKitchenCheck-in

4.94 out of 5 average rating, 114 reviews

A charming exterior of Henry House is presented under a clear evening sky. The entrance features a welcoming pathway leading to a stately door with red accents, flanked by well-maintained greenery and softly lit windows capturing the inviting atmosphere inside.

Apartment in Stratford

Lake Suite at Henry House Stays

Indoor spacesKitchenWalkability

4.92 out of 5 average rating, 304 reviews

A serene view of the cabin is reflected in the tranquil pond, surrounded by lush trees. Red outdoor chairs are positioned nearby, inviting relaxation by the water's edge, while the cabin's simple design complements the natural landscape.

Cabin in Windham Centre

The Kiln - Stay Longer Save More!

Indoor spacesKitchenTV

4.96 out of 5 average rating, 178 reviews

A modern kitchen features sleek white cabinetry and dark countertops. Appliance details include a microwave and a stove. Various utensils and kitchenware are organized neatly, and a small coffee station with a coffee maker is visible on the side. Soft lighting enhances the welcoming ambiance.

Apartment in Waterloo

Barb's Place

Indoor spacesKitchenSleep quality

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 203 reviews

A cottage is surrounded by vibrant red foliage, showcasing a blend of natural colors. The exterior features light wood siding and a tiled roof, with large glass doors leading to a patio area. Lattice work adorns parts of the structure, adding texture and visual interest.

Guesthouse in Delhi

R&R La Petite Rhineland Retreat

FamilyIndoor spacesBathroom

4.99 out of 5 average rating, 204 reviews

The exterior of a cabin is depicted, featuring wooden siding and a stone base. A small wreath decorates the entrance, which is flanked by a snow-covered landscape. Tall trees stand in the background, hinting at the surrounding nature.

Cabin in Hamilton

The Fox's Retreat - A Cozy Cabin for Two

Indoor spacesKitchenCheck-in

5.0 out of 5 average rating, 216 reviews

A rustic cottage with wooden siding and a welcoming entry, features double French doors framed by vibrant red flowers. A spacious outdoor area includes a patio with seating and a partially shaded structure nearby. The surrounding landscape is well-maintained with green grass and shrubs.

Tiny home in Caledonia

Tiny House with Nature Views and Swimming Pond

FamilyKitchenSleep quality

4.87 out of 5 average rating, 135 reviews

A well-lit backyard features an inviting in-ground pool, surrounded by landscaped grass and illuminated by string lights. A wooden deck is accessible, along with seating areas, including a hammock. The brick home stands in the background, highlighting a warm nighttime ambiance.

Home in London

Walk-Out | Patio | Pool | Private:Open-Concept:BBQ

KitchenFamilyPool

4.95 out of 5 average rating, 217 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

FamilyIndoor spacesCheckout

4.99 out of 5 average rating, 116 reviews

Apartment in Waterloo

Charming Hideaway: 1-bedroom Apartment

FamilyKitchenView

4.88 out of 5 average rating, 105 reviews

A modern living space features a beach-themed wallpaper with palm trees. A light-colored sofa and a glass coffee table are positioned alongside a wooden accent table. The kitchen area includes a spacious island and appliances, while natural light fills the room through large windows.

Apartment in Waterloo

1BD · The Laundry Rooms, Waterloo - One Bedroom

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