Holiday houses in Woodstock

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Top-rated holiday rentals in Woodstock

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Top Guest favourite
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
5 out of 5 average rating, 108 reviews

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.

Top Guest favourite
Guesthouse in Shakespeare
5 out of 5 average rating, 43 reviews

Cozy country getaway -clawfoot tub & starry nights

Escape to our peaceful 2-bedroom country guest house, nestled among beautiful farmland with stunning views. A tranquil retreat or a base to explore the nearby Stratford area, this modern farmhouse-style suite is the perfect getaway for up to 4 guests. Relax in a cozy yet spacious setting featuring two queen beds, an electric fireplace, and a walk-in shower with a luxurious soaker tub. Enjoy the quiet of the countryside with an outdoor fire pit and BBQ. Washer and dryer and Wi-Fi are included.

Superhost
A spacious living area is presented, featuring a gray sectional sofa and a light-colored coffee table on a textured rug. A television stands on a low console, while a workspace with a desk and chair is situated in the corner. Bright lighting enhances the neutral décor.
Apartment in Zorra
4.83 out of 5 average rating, 120 reviews

Cozy, spacious, homely and clean Basem't apartment

Bring yourself or family to this great , peaceful and spacious basement with lots of room for some family time, vacation or during transit from the airport. Our "newly finished basement " is a spacious 2 bedroom, 1 bathroom apartment, that has a cozy home feel with its woodern floors. It is 10mins from London Airport and a Tesla pick-up and drop-off can be negotiated. The home is big enough for a group of 4 individuals . Zorra boasts of its quiet, peaceful, friendly and inclusive nature.

Top Guest favourite
A cozy seating area features a light gray sectional sofa adorned with decorative pillows. The deep blue wall is complemented by two framed artworks, enhancing the space's style. A small round basket rests on the floor, contributing to the casual ambiance.
Cottage in Stratford
5 out of 5 average rating, 137 reviews

Farmhouse | 7 mins to Dwntwn | Games | Sleeps 7

Welcome to our charming rural retreat, where we love hosting guests and making every stay extra special - plus we're only 7 minutes to downtown Stratford and 17mins from St. Mary's! Many years ago this is the site of the Harmony Inn - a once thriving Mill town. Today our fully renovated 1200 sq ft heritage cottage is the perfect choice for your group meetup or theatre stay. NEW for 2025!! We've updated all the furniture, bedding and decor... come check out our NEW curated designer space!

Superhost
A serene outdoor seating area features two light-colored chairs facing a small red table. Beyond lies a calm lake surrounded by trees, with a hanging ornament visible above. The ground is covered in grass, offering a peaceful spot to relax.
Cottage in New Dundee
4.86 out of 5 average rating, 243 reviews

Cozy Waterfront Cottage

Cozy waterfront cottage. Nestled in the woods on a private lane. Enjoy this cottage vacation while being only minutes from the city of Kitchener. Take in the fresh air, cast a rod in the lake, float around in a canoe, enjoy a fire under the stars, or just hang out on the deck. In winter, explore the frozen lake with skates or snowshoes. Propane fireplace is available for emergency heat only in winter. In the event of a power outage this would be the only heat available. We allow one pet.

Top Guest favourite
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
4.9 out of 5 average rating, 194 reviews

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.

Top Guest favourite
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.
Guesthouse in Springfield
4.84 out of 5 average rating, 160 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

Top Guest favourite
A bright and inviting living area features a cozy sectional sofa with decorative pillows, positioned beside a well-lit kitchen with modern appliances. Large windows allow natural light to fill the space, highlighting the warm wood flooring and contemporary furnishings.
Guest suite in Stratford
4.97 out of 5 average rating, 400 reviews

Spacious Suite • Short drive to Downtown/Festivals

Minutes from the Stratford Festival and direct down Huron St. to the downtown core, this private two-level guest suite offers a quiet, comfortable retreat with easy access to theatres, restaurants, grocery stores and shops. Ideal for festival-goers, weekend getaways, and longer stays. Enjoy self check-in with private keyless entry and convenient free parking. Guests love the High Speed Fibre Optic internet (551 MBPS), the well equipped eat-in kitchen, and the quiet backyard patio.

Superhost
Townhouse in Woodstock
5 out of 5 average rating, 3 reviews

Epitome 3 bdrm 2.5 bath. Near Hospital and 401

This beautifully designed home is perfectly located near the hospital, Walmart, bars and restaurants within walking distance. - Master bedroom has a comfortable King size bed with ensuite bathroom - Fully equipped kitchen with everything you need to cook and enjoy your favorite meals - Close proximity to local amenities and services Whether you're visiting for business or pleasure, this is the perfect place to call home. Book your stay today and experience the best of Woodstock!

Guest favourite
A bright living space features large arched windows allowing natural light to fill the room. A wall-mounted television sits atop a light-wood media console. An armchair and a small side table are positioned on a textured area rug, enhancing the minimalist decor.
Apartment in Woodstock
4.94 out of 5 average rating, 48 reviews

The Charlotte | King Bed • Downtown Woodstock

Experience The Charlotte — a peaceful boutique retreat blending timeless minimalism with modern comfort. Relax in a spacious king-sized bed, enjoy a sleek, fully equipped kitchen, and unwind in a calming, uncluttered space designed for rest. Located in downtown Woodstock, you’re just steps from local shops, cafés, and restaurants. Whether you’re visiting for business or leisure, The Charlotte offers a serene, sophisticated stay with the convenience of a walkable location.

Top Guest favourite
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
4.99 out of 5 average rating, 100 reviews

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!

Superhost
Apartment in Woodstock
4.81 out of 5 average rating, 125 reviews

Entire Rental Unit- Close to Woodstock Hospital

Enjoy this Private Unit located in a Residential Neighborhood Near Woodstock Hospital. Private entrance with two free parking on the driveway. Full kitchen well equipped for longer stays, full bathroom, a laundry room, 1 bedroom, a living area, and dinning. Two Minutes to so many restaurants, grocery stores recreation center, parks, community complex and three Minutes to highway 401.

Popular amenities for Woodstock holiday rentals

When is the best time to visit Woodstock?

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Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Woodstock?

    Yes! Work meets play with ease at over 30 vacation rentals in Woodstock featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in Woodstock?

    Woodstock has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Woodstock?

    Experience the best of Woodstock with our house rentals, starting at about $10 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Woodstock have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodstock have a kitchen?

    Absolutely! We offer over 20 house rentals with a kitchen in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Woodstock have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Woodstock have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Woodstock. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Woodstock?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 20 homes with a kitchen, over 30 homes with free parking, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about holiday rentals in Woodstock

  • Total holiday rentals

    Explore 50 holiday rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at $14 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,170 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Woodstock holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woodstock rentals

  • 4.7 Average rating

    Woodstock stays receive an average rating of 4.7 out of 5 from guests

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