Holiday houses in Woodstock

The Loft on Downie - Downtown Stratford

Located on the top floor, with a view of downtown, our 450 square foot condo is steps away from the heart of downtown Stratford and all it has to offer including cozy coffee shops, elegant restaurants, the Avon Theatre, close to the famous Stratford festival, and other shops for all to enjoy. Perfect for a couple’s getaway or to enjoy as friends travelling together. Our condo offers all the essentials including a luxurious queen bed, fully equipped kitchen, a 55” smart TV and ensuite laundry.

The Avon Festival Get-Away

We take pride in ensuring our place is clean, polished and comfortable. A 16 min walk to the Festival Theatre on Queen St. It is a pretty walk along the arboretum and Avon River. We have a well equipped kitchenette, and a high end Kreuig for your tea, coffee, and chai latte needs, all free of charge - also has a cold brew feature! Our basement suite is good for families, couples, solo adventurers, business travellers, and furry friends (pets). The suite has free parking and a private entrance.

Woodstock Hideaway

This separate entrance cozy AirBnb offers space for up to 6 people. Cook, charge your EV, play games, & watch movies! The apartment is stocked, clean, and stylish, with thoughtful amenities to make your stay comfortable and enjoyable. Walk to trails, parks and downtown shops and restaurants or venture further to Terra Nova Nordic Spa, Canada's largest antique mall, Gunn's Hill Cheese Farm or a bit further to Stratford or Walter's Music Venue for dinner and a show. There is plenty to see and do!

Tranquil Tiny House Retreat 4-Season Radiant Floor

Take it easy at this unique cabin experience in the city. The Tiny House is a private 9’ x 12’, fully insulated, 4 season cabin with a couch, kitchenette with running water, queen bed, Loftnet hammock & outdoor shower. Enjoy the natural beauty of our half acre tree-filled backyard, yet still close to downtown Guelph. This is a glamping experience that requires appreciation for tiny house living. Guests have access to a separate portable washroom, by walking about 100ft to the back of the yard.

7 mins to Dtwn Theatres, Holiday Getaway - 2KG/1QN

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!

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!!

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

Welcome to Cowtown. 2 bedroom apartment

Welcome to your perfect getaway in the heart of Woodstock! This cozy second story apartment blends comfort & convenience. Enjoy 2 inviting bedrooms with luxury mattresses for a great night’s sleep! A fully equipped kitchen and open plan living area featuring Roku TV and Wi-Fi. You'll have easy access to local shops, restaurants, hospital and the 401/403 when staying with us. Explore nearby Southside Park or take a short drive to the beautiful countryside and scenic walking trails!

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.

Comfortable/Convenient Kitchener/Waterloo Location

Great apartment in a century house that's a 10-minute walk to downtown Kitchener or Waterloo. Parking, washer/dryer, fast wifi, full kitchen, full bathroom, large bedroom with queen bed, quiet desk work area, living room TV with Netflix, Prime, and Disney. 7 minute drive/transit ride to UW, 5 minute drive/transit ride to WLU, Conestoga College, and 5-minute walk to Google Canada. Frequent street cars and buses 5 houses away on King Street.

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!

Brand new studio suite

Beautiful, new, self contained studio suite with large, Luxury hot tub. Come and stay with the crew of the Stratford Festival. Walking distance to theatres and city centre. Private driveway with keypad entry. The studio suite faces the garden. It has a queen sized Endy bed. Please feel free to have meals or drinks on the patio space next to your suite and enjoy a hot tub and a glass of wine.