Vacation rentals in Woodstock

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Quick stats about vacation rentals in Woodstock

  • Total vacation rentals

    Explore 70 vacation rentals in Woodstock

  • Nightly prices starting at

    Woodstock vacation rentals start at G$6,280 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,400 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Woodstock vacation 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

Top-rated vacation rentals in Woodstock

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
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.
Guest suite in East Zorra-Tavistock
4.92 out of 5 average rating, 102 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

Top guest favorite
Guesthouse in Shakespeare
5 out of 5 average rating, 66 reviews

Cozy modern country getaway-Minutes from Stratford

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.

Top guest favorite
Cottage in Stratford
5 out of 5 average rating, 150 reviews

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.

Top guest favorite
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, 331 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 favorite
A welcoming living area is displayed with a cozy gray sofa and a bright yellow armchair. A wood-burning stove stands beside a wall-mounted television. Natural light enters through a window, illuminating the area rug and a bookshelf filled with books.
Barn in Gads Hill
5 out of 5 average rating, 140 reviews

The Country Nook

This barn style cabin is located 10 -15 minutes from Stratford, Ontario the home of Stratford Festival. This newly renovated 1.5 floor retreat offers an open concept living area, along with two bedrooms with queen size beds. Large windows and a 16 foot ceiling height in the living room add to the brightness of the space. This home away from home offers both comfortable seating inside and a screened in patio nestled into the trees. A way to get away from the city and enjoy the fresh air.

Guest favorite
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
4.94 out of 5 average rating, 80 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

Guest favorite
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
4.93 out of 5 average rating, 61 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 favorite
Guest suite in Hamilton
4.99 out of 5 average rating, 75 reviews

Summertime! Steam shower+breakfast+rooftop hottub

Nestled in a picturesque escarpment community overlooking the historic town of Dundas, The Hayloft is a charming getaway for anyone looking for an escape and a breath of fresh air. Relax in the steam shower inside or the hot tub on the fully private rooftop deck overlooking gardens. Take a nap on the lounge chairs. Visit with the chickens, make friends with the fish or the frogs. Unwind at night with a movie in bed, with breakfast (surcharge) in the morning.

Top guest favorite
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
4.99 out of 5 average rating, 203 reviews

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.

Top guest favorite
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, 94 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.

Guest favorite
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.
Guesthouse in Tillsonburg
4.97 out of 5 average rating, 109 reviews

BosHaven Guest House *Hot tub*

Charming and inviting space minutes away from Tillsonburg offering comfort and convenience. This well-appointed house features a cozy atmosphere with modern amenities, including a full kitchen, bath & washer/dryer as well as an outdoor space including seating & propane fireplace & bbq. Located 20 minutes away from Port Burwell beach. It’s the perfect spot for a memorable stay!

Top guest favorite
Home in Norwich
4.97 out of 5 average rating, 34 reviews

The Cozy Nest: Private Home near Downtown Norwich

🏡✨Welcome to "The Cozy Nest" in Norwich! 🏡✨ Discover your perfect retreat in the heart of this charming, quaint town located in Oxford County. 🏘️🌿 This cozy and inviting home offers a relaxing escape with a perfect blend of comfortable indoor living and a spacious private outdoor oasis—ideal for couples or a small family getaway. 🌷☀️☕

Popular amenities for Woodstock vacation rentals

When is the best time to visit Woodstock?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$16,957 GYDG$16,957 GYDG$16,957 GYDG$19,260 GYDG$20,516 GYDG$20,307 GYDG$15,911 GYDG$18,213 GYDG$15,911 GYDG$18,632 GYDG$19,260 GYDG$20,726 GYD
Avg. temp-5°C-4°C0°C7°C14°C19°C21°C20°C16°C10°C4°C-2°C

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.

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