Holiday houses in Olalla

The Second Breakfast Hideaway

Second Breakfast Hideaway is your own little slice of Middle-earth. This cozy, halfling-inspired retreat offers a charming escape with its round door, rustic details & cozy, nature-filled surroundings. Whether you’re an Hobbitier at heart or just seeking peace, this enchanting whimsical hideaway is the place for you. It’s the perfect spot enjoy a second breakfast or curl up by the fire. Located just minutes from local attractions, it's the ideal place to unwind and embrace your inner halfling.

Woodlands Nordic Spa Retreat

Recharge at this romantic retreat, complete with outdoor sauna. The cabin independently nestles on a forested hillside at the top of Trepenier Bench, overlooking Pincushion and Okanagan Mountain. Unwind and relax with a private, wood-burning sauna, cold plunge tank and outdoor fire pit. The cabin is close to wineries, trails and restaurants, located minutes from downtown Peachland. Big White, Silver Star, Apex and Telemark all within 1.5 hr distance. Let us host your time-out from normal life!

Blush Bliss – Herrera Vineyard Estate Home

Enjoy an amazing vacation at a picturesque countryside retreat. It’s the perfect place for outdoor enthusiasts and wine lovers to reconnect with nature. Relax on the patio while admiring the gorgeous view of the mountains, relax in the sunroom, and access fantastic wineries, cideries, & a distillery a short drive away. The property is shared with a second vacation home, separated by a large courtyard to ensure each guest's privacy. For package rental options, go to: airbnb.ca/h/hererrapackage

Beautiful Skaha Lake View Studio

Welcome to your perfect getaway in the heart of the Okanagan Valley This new, stylish studio offers a spectacular unobstructed 180-degree view of Skaha Lake, surrounding mountains, and vineyard. The large studio is modern in design and decor, has a king sized bed, sitting area, well equipped kitchenette.and a large private outdoor living space. Whether you're enjoying your morning coffee or unwinding with a glass of local wine on your patio in the evening, this view will leave you in awe.

Cawston Farm Stay

Unwind in a private suite for two adults, surrounded by orchards, vineyards, and friendly animals. Enjoy modern comforts with rustic charm. Close to cafés, restaurants, grocery stores, and shops—plus top wine and cider tastings, live music, and outdoor adventures in the Similkameen Valley. Traveling with children? Let us know—child accommodations may be available upon request. Unfortunately, we are not able to accomodate pets. As an operating farm with livestock, it is too much of a risk.

Pincushion Cottage

Our charming rural cottage is tucked into the mountainside, surrounded by the natural beauty of sage and mountain flowers, with spectacular views in all directions. The Pincushion Mountain hiking trail leading to Keremeos Columns Provincial Park is literally out the front door. Minutes away from the fruit stands, wineries, and cideries of the Similkameen Valley wine region, the cottage is fully equipped for you to enjoy cooking up your own tasty dishes from fresh local organic ingredients.

Cheerful Executive Style 4 Bedroom Home

Bring the whole family to this great place with lots of room for fun. This 4 bedroom, 2 bathroom home has 3 queen beds, 1 king bed, 1 hide-a-bed and a crib, living room, laundry room and fully equipped kitchen. Whether you're looking for business or pleasure, this house has it all. Your hosts are located right next door, so if you've forgotten something or just need extra of something, we're only a text or phone call away. Prefer talking to us face to face, we're a short walk away.

Similkameen Sunset Suite

Brand-new 2-bedroom suite on a peaceful riverfront orchard with beautiful mountain views. Enjoy nearby walking trails, great river swimming spots, and easy access to local lakes, wineries, fruit stands, and more. You’re also just a short drive from both Apex and Mount Baldy ski hills. The suite includes a heat pump and AC for year-round comfort. It’s still new and kept simple - minimal décor, but fully equipped with TV and Wi-Fi. Clean, comfortable, and perfect for a relaxing stay.

Cozy guesthouse with Osoyoos Lake view!

Take it easy at this unique & tranquil getaway. Retreat away from busy life and come stay at our cozy mountain suite. We are located only 15 minutes away from town giving a serene getaway feel while allowing you access to the essentials. Enjoy your coffee on the patio while watching the sunrise and end the day with a local glass of wine while watching it set. Spend your days exploring what Osoyoos has to offer which includes hiking, golfing and swimming in BC's warmest lake.

Orchardside Cabin

A small, quiet, and cosy cabin surrounded on all sides by gorgeous mountain views. The perfect place to escape the noise and enjoy a rustic retreat, while still enjoying all the comforts and conveniences of the modern world. All the while being immersed in scenery that remains beautiful all year round. The driveway leads right up to the cabin entrance, and it's location on the property will provide you complete privacy with which you can enjoy your stay.

Scandinavian Escape

When palm springs meets a peaceful lush secluded forest - welcome to our Scandinavian escape. This private hotel style suite has its own separate entrance, patio and is the perfect spot to enjoy the beauty and serenity of nature while only being 12 minutes from Osoyoos & 30 minutes from Mt. Baldie ski resort. Step back in time with the mid century decor but enjoy the luxury of a rainfall walk in shower, workspace and mini kitchen to prep any meal.

Owl Studio Guesthouse at Farmersdotter Organics

Owl Tiny Studio Guesthouse at Farmersdotter Organics (See also Osprey Tiny Studio Guest House). One of two architecturally designed studio guest houses Owl and sister unit Osprey are situated front and centre at Farmersdotter Organics, a certified organic garlic farm ideally located in the heart of the Similkameen Valley wine region and Canada's organic farming capital.