
Holiday rentals in Woodstock
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Top-rated holiday rentals in Woodstock
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The Kiln - Stay Longer Save More!
Escape life's bustle & retreat to this 4-season cabin, which sits on an 80 acre farm overlooking a tranquil pond. Cozy up inside by the wood stove, play some of the many games provided, or kick your feet up & catch up on your favourite shows as satellite & wifi are accessible. Get outdoors to wonder the fields and go for long forest walks along the many trails, or sit around the fire pit roasting hot dogs and marshmallows! Make sure to keep an eye though, as you're bound to see some wildlife!

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?

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.

Relaxing Forest-View Studio with Private Entry
Stay in this unique and spacious studio with a view of a lush forest and large garden with outdoor patio seating. With a private entrance and the entire basement floor to yourself, you'll enjoy a quiet, comfortable, and fully private stay. Conveniently located just minutes away from Conestoga College, the 401, Roseville Estate and Whistle Bear Golf Course. (6-10 min drive). Also less than 5 minutes away (driving) from a large plaza(Zehrs, Shopper Drug Mart, LCBO, Tim Hortons, and more).

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!!

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.

"Cottage Home On The River" 1 Bedroom
Welcome to Speed Island Trail! Nestled on 1 Acre property in a forested area that backs onto the Speed River. Enjoy Beautiful views all season long with large floor to ceiling windows and wildlife right outside your door. It is just like being out at the cottage. This beautiful one bedroom house is beautifully decorated, has a large kitchen and a breakfast bar. Enjoy the large sunroom and deck where you can sit back and relax. Added bonus the Chickadees eat right off your hand!

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.

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!

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.

Oliver's Tiny Home In The Forest | Sauna & Hot Tub
Escape to the heart of a Carolinian forest in Simcoe, Norfolk County — a private tree farm sanctuary designed for those who crave stillness. Sink into the hot tub, warm your soul in the wood-burning sauna, or brave the cold plunge bucket on warm days. Surrounded by towering trees and birdsong, this cozy retreat welcomes couples, friends, and solo adventurers year-round. Unplug. Breathe. Belong to the forest.

Juno Lofts: Memories of Polonnaruwa
Polonnaruwa Loft: Bohemian Elegance in Heritage Downtown. Perched atop a 1893 heritage property, our loft brings Sri Lankan charm to Stratford. Located in the city centre, enjoy top dining across the street, a 2-min walk to Avon Theatre, and 5 mins to Avon River. Features bohemian design, with access to 3rd floor free laundry. Perfect for those seeking a unique stay near Stratford Festival theatres
Popular amenities for Woodstock holiday rentals
Other great holiday rentals in Woodstock

Modern & Spacious 1908 Home

The Kabin

Bradshaw Lofts: The Brixton King Suite

Private Retreat with Infrared Sauna

The Ingersoll Hideaway-close to 401 and amenities

Spacious 3 Bedroom Home in Serene Neighborhood

La Casita on Hampton Lower 25 Balmoral

Cozy 2 Bedroom Apartment Downtown New Hamburg
When is the best time to visit Woodstock?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $104 SGD | $104 SGD | $104 SGD | $118 SGD | $126 SGD | $125 SGD | $98 SGD | $112 SGD | $98 SGD | $114 SGD | $118 SGD | $127 SGD |
| Avg. temp | -5°C | -4°C | 0°C | 7°C | 14°C | 19°C | 21°C | 20°C | 16°C | 10°C | 4°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 holiday rentals in Woodstock

Total holiday rentals
Explore 60 holiday rentals in Woodstock

Nightly prices starting at
Woodstock holiday rentals start at $39 SGD 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 & child-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
50 of Woodstock holiday rentals include wifi 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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- Wilfrid Laurier University
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- Port Stanley Beach
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- FirstOntario Centre
- Western University
- Museum
- Mohawk College
- McMaster University
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