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.

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 Paris
4.9 out of 5 average rating, 197 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 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
4.96 out of 5 average rating, 316 reviews

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!!

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, 164 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 modern living area features a blue and green seating arrangement, complemented by a dark blue area rug. A coffee table sits centrally, while a wall-mounted television displays content. The open layout leads to a kitchen with bar seating, brightening the space with natural light.
Apartment in Woodstock
4.96 out of 5 average rating, 72 reviews

Opulent 2 bedrooms apartment

Stay comfotably in this perfectly appointed 2 bedroom apartment, complete with: - 2 queen-sized beds for a restful night's sleep - Fast internet Full kitchen equipped with: * Coffee maker * Air fryer for healthy cooking options * Toaster *Rice cooker and enough kitchen utensils for effortless meal prep Ideal for couples, friends, or small families, this apartment has everything you need to feel right at home. Book now and make yourself comfortable!" - Each room has its own heat/AC

Top Guest favourite
Cottage in Stratford
5 out of 5 average rating, 139 reviews

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

March Special: Stay 2+ nights and enjoy a complimentary local bakery breakfast basket. Stay 3+ nights and we’ll include 4 Stratford Chocolate Trail passes, a self-guided tasting experience at participating downtown shops. Cozy renovated 1200sqft farmhouse just 7 minutes from downtown Stratford, ideal for March Break or group getaways. Sleeps up to 8 with 2 kings, 1 queen, and a pop-up sofa bed. Bright, comfortable space for gathering, games, and relaxed evenings together.

Top Guest favourite
A cozy living room features a light-colored sofa with patterned cushions, accompanied by two green armchairs. A wooden coffee table sits atop a textured area rug. Large windows allow natural light to illuminate the space, which includes a wall-mounted TV and a wooden cabinet.
Home in Ingersoll
5 out of 5 average rating, 14 reviews

Beautiful stunning home

Relax and unwind in this beautiful 2 bedroom home, with an incredible outdoor space! Upstairs office nook, lots of space on main floor , with high end appliances and cookware! Be a chef in the well equipped kitchen with granite countertop. Weber Gas bbq just off the side door on deck.! Cozy living room space with 65” smart tv and Games table . House has on demand hot water ! High speed internet , everything you need is here for a memorable home away from home experience

Top Guest favourite
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
5 out of 5 average rating, 197 reviews

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.

Guest favourite
A spacious living area features a comfortable chair facing a modern television, complemented by natural light from an arched window. The sleek kitchen area includes contemporary cabinetry and stainless steel appliances, set against a light wood floor that enhances the airy feel of the space.
Apartment in Woodstock
4.94 out of 5 average rating, 53 reviews

Modern Downtown Suite | King Bed | The Charlotte

A clean, modern downtown stay designed for comfort and simplicity. Relax in a king-sized bed, enjoy a fully equipped kitchen, and unwind in a space that’s easy to settle into the moment you arrive. Located in the heart of Woodstock, you’re just steps from shops, cafés, and restaurants—including Tempo right across the street. On the main floor, you’ll find On Trend, a boutique clothing shop—perfect for a quick browse or picking something up during your stay.

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 Paris
4.99 out of 5 average rating, 105 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!

Top Guest favourite
A spacious master bedroom features a large bed with white linens and decorative pillows. Exposed brick walls enhance the rustic charm, complemented by wooden beams overhead. A cozy bench covered in a soft throw sits at the foot of the bed, with framed art arranged above.
Apartment in Stratford
4.96 out of 5 average rating, 439 reviews

Wow, Two Chic King suites- Walk to DT/Theatre's

Experience all that Stratford has to offer from this updated 2-bed, 2-bath vacation rental home. As former servants quarters, this unique home was the first house built on the north side of the river in Stratford. With sleeping for 6 and a furnished outdoor space, plus a prime location within walking distance of town's theatres, there's no better place to spend your Ontario getaway then this charming abode!

Top Guest favourite
An open living area features modern furnishings, including soft armchairs and a sleek coffee table. A staircase leads to a lofted bedroom area with a green bedspread. Natural light floods the space through large windows, creating a welcoming and airy atmosphere.
Apartment in New Hamburg
5 out of 5 average rating, 77 reviews

Nith River Loft

Nith River Loft is a custom, luxury loft completed in 2020. Nestled in a treed, rural setting, the loft offers a serene experience. This picturesque oasis is accented by a private deck, fire pit and walking trails. Whether visiting friends and family, exploring local sites or seeking a cozy little private setting for rest and relaxation, The Nith River Loft is an impressive destination.

Popular amenities for Woodstock holiday rentals

When is the best time to visit Woodstock?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$117 NZD$155 NZD$126 NZD$156 NZD$166 NZD$165 NZD$129 NZD$148 NZD$129 NZD$151 NZD$156 NZD$168 NZD
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Frequently Asked Questions

  • What are the best places to stay in Woodstock?

    Woodstock has vacation rentals in downtown, historic quarters, and residential neighborhoods near parks. Staying around these areas gives easy access to local attractions, green spaces, and eateries.

  • What are the best things to do in Woodstock with kids?

    Kids often enjoy playgrounds at Southside Park, hands-on exhibits in the Woodstock Museum, and attending seasonal fairs or festivals. Outdoor spaces and conservation areas around the city are popular for picnics, games, and wildlife watching.

  • What are some of the best things to do in Woodstock?

    Explore Pittock Conservation Area and Southside Park, discover local history at the Woodstock Museum, and browse artisan shops in the city center. Festivals, farmers markets, and live events add to the city’s welcoming atmosphere.

  • How is the weather in Woodstock?

    Woodstock has summer temperatures around 57–79°F (14–26°C) in August, cooling to 41–59°F (5–15°C) in October. Late summer often feels mild and comfortable, with rainfall increasing toward autumn.

  • When is the best time to visit Woodstock?

    Late spring and summer are often recommended for visiting Woodstock, thanks to milder weather, blooming parks, and community events. Autumn draws visitors for local harvest festivals and colorful foliage.

  • What are the best places to visit in Woodstock?

    The Woodstock Museum, Pittock Conservation Area, and Southside Park are frequently suggested for their history, natural beauty, and family-friendly spaces. Downtown mixes heritage architecture with artisan shops and casual eateries.

  • What are some hiking trails in Woodstock?

    Woodstock has scenic trails in areas such as Pittock Conservation Area and Southside Park, where visitors can explore woodlands, lakeside paths, and natural habitats. These spaces are frequently suggested for walking, cycling, and bird watching.

  • What are some family activities we can do in Woodstock?

    Families can explore playgrounds in Southside Park, enjoy interactive exhibits at local museums such as the Woodstock Museum, or spend the day picnicking by the water in conservation areas. Seasonal festivals and farmers markets around town provide opportunities for hands-on fun and discovery.

  • What are some of the best day trip ideas from Woodstock?

    Explore nearby conservation areas for nature walks, visit small towns with unique heritage sites, or discover regional wineries and craft breweries. Museums, markets, and riverfront parks in surrounding communities are frequently suggested for day trips.

  • Are there any pet friendly accommodations available in Woodstock?

    Many vacation rentals in Woodstock welcome pets, especially in residential neighborhoods and near green spaces. Parks and conservation areas make it simple to enjoy outdoor activities with your dog while staying locally.

  • What are some local tips for visiting Woodstock?

    Locals often suggest exploring the city’s parks early in the day and checking for seasonal festivals or farmers markets on weekends. Be sure to try artisan cheeses and connect with artists at local galleries.

  • What is Woodstock known for?

    Woodstock is known for its agricultural heritage and locally rooted arts scene, with historic museums, summer fairs, and distinct Victorian architecture. The city often draws visitors for its vibrant community events and access to outdoor recreation.

  • What are the best hidden gems to explore in Woodstock?

    Woodstock has independent galleries, local history museums, and quiet parks that are often recommended for visitors looking to explore off the main path. You can discover handcrafted goods at artisan shops or stroll heritage neighborhoods for a glimpse into the city’s roots.

  • What are the best foods to try in Woodstock?

    Locally crafted cheeses, seasonal produce from farmers markets, and classic comfort foods such as pies, breads, and maple-flavored treats are frequently suggested in Woodstock. The city’s cafes and bistros feature a mix of traditional Canadian flavors and international options.

  • What should I bring for a trip to Woodstock?

    Pack comfortable walking shoes, layered clothing for shifting temperatures, and a light waterproof jacket. A camera and reusable water bottle can help you explore local trails, parks, and markets with ease.

  • What is the nightlife in Woodstock like?

    Woodstock’s nightlife features relaxed pubs, casual eateries, and live music venues, especially around downtown. Local cafés and gathering spaces mix acoustic performances with friendly social atmospheres.

  • What are the most popular events or festivals in Woodstock?

    The Woodstock Fair, often recommended in late summer, brings agricultural exhibits, family entertainment, and local music. Seasonal celebrations and craft fairs around the city highlight Woodstock’s community spirit and creative traditions.

  • Are there family friendly vacation rentals in Woodstock?

    Woodstock has a variety of family-friendly vacation rentals, especially near parks and quiet residential neighborhoods. Homes and apartments in these areas give families space to relax and easy access to local attractions.

Quick stats about holiday rentals in Woodstock

  • Total holiday rentals

    Explore 60 holiday rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at $51 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,330 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 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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