Vacation rentals in Woodstock

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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 small cabin with a red roof is set amidst a green lawn, surrounded by trees. A campfire pit, with smoke rising gently, is situated in front of the cabin. A rustic wooden table is nearby, enhancing the natural outdoor setting.
Tiny home in Wellesley
4.99 out of 5 average rating, 139 reviews

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, canoe. 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?

Top guest favorite
A modern outdoor table features a glowing fire element at its center, providing warmth and ambiance. In the foreground, three clear glasses filled with water rest on the table. Lush green trees form a serene backdrop, creating a peaceful setting.
Cottage in Stratford
5 out of 5 average rating, 145 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 white exterior features a welcoming entrance door surrounded by colorful flower pots. The door includes a glass panel and is framed by well-maintained greenery, creating a pleasing view at the unit's entrance. A large window reflects the outdoor setting.
Apartment in Thamesford
4.96 out of 5 average rating, 323 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 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, 168 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

Guest favorite
Apartment in Woodstock
4.93 out of 5 average rating, 75 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 favorite
A shaded outdoor seating area features comfortable chairs and a table with two cups. A hot tub is visible nearby, alongside a grill. The wooden deck overlooks a serene lake, framed by trees, with a pop of color from a red umbrella.
Cottage in New Dundee
4.9 out of 5 average rating, 135 reviews

Cosy Lakefront Cottage

Enjoy 150 feet of lakefront just outside the city limits. This fully remodeled cottage has fun for all to enjoy. There are kayaks, a canoe and a paddle boat for those that live on the water. We also have floaties if you just want to lounge and relax by the water. In the winter months you can also bring your ice skates and enjoy skating on the lake and then coming inside for a hot drink by the propane fireplace. The 800 square feet of deck overlooks the water for all your needs.

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
4.95 out of 5 average rating, 57 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
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, 194 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
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
4.96 out of 5 average rating, 107 reviews

Luxury Oasis with Hot Tub/Pool

Forget your worries in this spacious and serene space. Our Apartment offers you the chance to get away from it all with luxurious extras from a romantic soak in our hot tub or swim in our seasonal pool. Spoiled with robes to use during your stay, or a coffee at our coffee, tea, and hot chocolate bar. Enjoy a romantic fire under the stars in a shared firepit, or relax in your beautiful patio area with your own bbq and beautiful outdoor lighting.

Top guest favorite
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, 109 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 favorite
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
4.97 out of 5 average rating, 172 reviews

R&R La Petite Rhineland Retreat

Nestled amidst a canopy of trees with a symphony of song, rests a petite cottage that offers a serene experience. This picturesque oasis is accented by a seasonal pool, private deck, and extensive landscaping adding to the air of tranquility. Whether visiting friends & family, exploring local sites or seeking a cozy little private setting for rest & relaxation, La Petite Rhineland Retreat is an impressive destination.

Superhost
Apartment in Woodstock
4.81 out of 5 average rating, 129 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 vacation rentals

When is the best time to visit Woodstock?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$16,942 GYDG$16,942 GYDG$16,942 GYDG$19,243 GYDG$20,498 GYDG$20,289 GYDG$15,896 GYDG$18,197 GYDG$15,896 GYDG$18,615 GYDG$19,243 GYDG$20,707 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.

Quick stats about vacation rentals in Woodstock

  • Total vacation rentals

    Explore 60 vacation rentals in Woodstock

  • Nightly prices starting at

    Woodstock vacation rentals start at G$6,275 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,330 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

    50 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

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