Family-friendly holiday rentals in Woodstock

5.0 out of 5 average rating, 119 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.

KitchenIndoor spacesBarbecue

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.

4.92 out of 5 average rating, 105 reviews

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

Indoor spacesKitchenGetting around

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

Make some memories in our quaint town and stay at our unique family-friendly home with a private indoor heated salt water pool & hottub in the basement. The pool room has a TV, air hockey table, Foosball and basketball game. The fourth bedroom doubles as a board and Video games room/gym and there is a hockey training center on the garage. The fenced backyard has a deck, propane BBQ and seating area, movie screen & projector, trampoline and fire pit (firewood provided). Fun for the whole family!

FamilyIndoor spacesAir conditioning

4.99 out of 5 average rating, 164 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?

Indoor spacesKitchenAccuracy

4.9 out of 5 average rating, 220 reviews

The historic home showcases a classic façade with white columns and a welcoming porch. Flower beds with vibrant blooms enhance the entrance, while a wrought-iron fence adds to the charm. A sign is visible, marking the property as 'Tea on the Grand'.

Loft in Brant

Historic Carriage House Flat STUNNING VIEW

Step back in time to 1850 while staying at the iconic historic home built by The Lumber Merchant. Stay in the suite featuring the original post and beam structure and still offering modern conveniences such as gas fireplace , heated stencilled ceramic floors. Enjoy the quality mattress set into a 200 yr old brass bed once owned by royalty. Escape down to the river where a little cabin sits. If you are lucky you will have deer, heron, beaver, fox and many more wildlife come to visit.

KitchenIndoor spacesLocation

4.96 out of 5 average rating, 339 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!!

KitchenIndoor spacesSolo travel

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.

4.85 out of 5 average rating, 176 reviews

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

Indoor spacesFamilyAir conditioning

4.98 out of 5 average rating, 275 reviews

A spacious living area features a green velvet sofa with a decorative pillow, a vintage trunk serving as a coffee table, and an ornate gold mirror. Natural light filters through tall windows adorned with flowing curtains, enhancing the room's classic charm.

Apartment in Stratford

GG’s Place | Character | Steps to Downtown

A charming queen bedroom apartment flooded with natural light and a simple yet chic design to accent the character and historic elements of the space. Fully equipped kitchen and a spacious living area, the apartment is a short walk to downtown restaurants, patios, coffee & independent shops. Wander a few minutes further and you will find yourself at Stratford's picturesque Lake Victoria park. Be sure to check out Pretty Pretty Boutique Suites as well! www.airbnb.ca/h/prettypretty

KitchenIndoor spacesLocation

5.0 out of 5 average rating, 209 reviews

A spacious living area is seen featuring two comfortable chairs and a rug positioned underfoot. Natural light streams through glass doors leading to an outdoor space. A cozy fireplace and a wall-mounted television enhance the inviting ambiance of the room.

Guest suite in Brant

Scenic Country Retreat

Escape the hustle and bustle of city life by slowing down and rejuvenating in our scenic guest suite. Nestled in scenic country surroundings, this beautifully appointed space offers the perfect blend of comfort and relaxation. Our prime location allows easy access to nearby city attractions while maintaining a sense of seclusion. Whether planning a quick getaway or an extended retreat, our suite is your ideal escape. ChatGPT can make mistakes. Check important info.

Indoor spacesFamilyView

4.99 out of 5 average rating, 209 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

Welcome to Triangle House, a unique double A-frame situated on a private 1.7 acre lot, fronting on the Conestogo river Only 6 minutes drive from St.Jacobs center, 1.5 hours drive from Toronto, 15 minutes drive from the University of Waterloo and 25 minutes to Elora. Bring the whole family. This 3 bed, 3 bath home comfortably sleeps 6. Soak in the countryside from the sprawling deck and grounds, while enjoying all the comforts of a modern home.

FamilyIndoor spacesAccess

4.88 out of 5 average rating, 116 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.

FamilyIndoor spacesQuiet

4.99 out of 5 average rating, 125 reviews

The exterior of a century home is highlighted, featuring a welcoming porch surrounded by lush greenery. A paved driveway leads to the entrance, with neatly trimmed grass and decorative landscaping enhancing the inviting appeal.

Home in Brant

Paris Oasis-The Maples on Brock

Stay in this immaculately renovated century home, which is just a short walk from downtown Paris and comes with all the perks and white-glove service of a 5 Star Hotel. If you’re searching for the perfect home for your next family vacation, stay-cation, business trip, or long-term rental that satisfies both luxury & location, then look no further. Save your dates now and secure a Paris holiday you’ll always remember!

KitchenFamilyQuiet

Popular amenities for Woodstock family-friendly rentals

Kitchen

Wi-Fi

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

Indoor spacesKitchenLocation

4.94 out of 5 average rating, 226 reviews

Farm stay in Eden

The Bunkhouse @ Stone Gate Farm & Sculpture Park

KitchenFamilyDecor

4.96 out of 5 average rating, 150 reviews

Guest suite in Kitchener

The Oasis

Indoor spacesFamilyHot tub

Guesthouse in Tillsonburg

An aerial view of a stylish living area displays a light-colored sectional sofa with decorative cushions. A dark coffee table complements the space, while a patterned area rug is visible beneath. The kitchen island, featuring a dark stone countertop, is situated nearby, enhancing the contemporary design.

4.98 out of 5 average rating, 122 reviews

BosHaven Guest House *Hot tub*

KitchenIndoor spacesTV

4.78 out of 5 average rating, 175 reviews

Home in Simcoe

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

Indoor spacesKitchenBackyard

4.91 out of 5 average rating, 223 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

Indoor spacesFamilyBarbecue

4.88 out of 5 average rating, 198 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

FamilyKitchenCheck-in

4.93 out of 5 average rating, 122 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

KitchenIndoor spacesLocation

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 227 reviews

Guesthouse in Breslau

House on the Hill

FamilyKitchenLocation

4.94 out of 5 average rating, 310 reviews

A spacious living area features a white leather sectional sofa and a circular coffee table on a light rug. The wooden ceiling and walls add warmth, while a staircase leads to an upper level. A dining area is visible in the background, alongside a rustic table.

Cabin in Cambridge

Forest Hideaway

Indoor spacesFamilyView

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.

4.97 out of 5 average rating, 151 reviews

Little Can in the Pines - Bunkie No. 1

KitchenIndoor spacesComfort

4.84 out of 5 average rating, 164 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

FamilyIndoor spacesWi-Fi

4.92 out of 5 average rating, 229 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 spacesFamilyDecor

4.92 out of 5 average rating, 227 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

Indoor spacesKitchenWalkability

4.91 out of 5 average rating, 627 reviews

Guesthouse in Guelph

Sweet Studio ~ Spacious Yard ~ Nature Haven ~ AC

FamilyKitchenShared spaces

4.92 out of 5 average rating, 355 reviews

A scenic view of the property is presented, featuring a charming lamp post in the foreground and a well-maintained pathway leading to the house. The exterior showcases a blend of traditional and modern architecture, surrounded by lush greenery and a carefully landscaped yard.

Guest suite in Newton

Century Home Apartment next to the G2G Trail

FamilyKitchenBreakfast

Family-friendly home rentals with a pool

4.88 out of 5 average rating, 134 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

Indoor spacesFamilyBathroom

4.97 out of 5 average rating, 201 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

FamilyKitchenDecor

4.99 out of 5 average rating, 201 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

FamilyKitchenWalkability

4.87 out of 5 average rating, 134 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

KitchenFamilyDecor

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

FamilyIndoor spacesValue

Place to stay in Caledonia

A private balcony offers a serene outdoor space, featuring two blue chairs positioned on a patterned rug. Lush greenery is visible beyond the railing, enhancing the tranquil atmosphere. The door leads back inside, completing this inviting area for relaxation.

4.99 out of 5 average rating, 102 reviews

Historic Attic Suite + Private Pool + River Views

Indoor spacesFamilyBackyard

4.88 out of 5 average rating, 112 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

Indoor spacesFamilyCleanliness