Holiday houses in Olalla

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.

Juccuzi & Stars 2 Bed Home on 1/2 Acre Okanagan

Take it easy at this unique and tranquil getaway on 1/2 acre!! Jacuzzi in the stars. Majestic Mountains surrounding Vineyards and Fruit Stands. 7 Lakes all within an HR drive. Essentials Provided. Best Rates for the area. Peachland Zipline, Loco landing Penticton Watersport Rentals at most lakes. Famous spotted lake is Cool and fishing on the dock is popular at yellow lake, also known for ice fishing in cold winter months. Fun for All! The Home has installed filter for drinking & cooking

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.

Bold Reserve – Herrera Vineyard Estate Home

Welcome to Casa De Hererra guest house! This inviting family home sits in the middle of a Vineyard. A great space to get together! Just minutes from local wineries, restaurants, cideries, fruit stands, scenic walking trails. Enjoy wine tastings, outdoor activities, and fantastic dining options! The property is shared with a second vacation home, separated by a large courtyard to ensure each guests privacy. For package rental options go to: airbnb.ca/h/hererrapackage

B & B Minute's walk to Lake

Escape to our peaceful garden retreat, only a minute’s walk from Skaha Lake. Perfect for a weekend getaway or short stay, it offers comfort, privacy, and a quiet connection to nature. Relax in the garden, explore local attractions, and enjoy the beauty of the Okanagan—all just moments away. Start your stay with a little treat! We provide complimentary muffins upon arrival as a warm welcome to help make your stay even more enjoyable. Municipal License - NOT REQUIRED

The Emerald Dome

Disconnect from the hustle and bustle of life and reconnect with nature in this peaceful dome located in Kaleden, BC. The dome is on 10 acres and borders 350 acres of crownland to explore. Includes a hangout area with a fire pit, patio table and chairs, solar lights, and an outdoor cooking area. There are lights and a charging station in the dome. **This is a rustic off-grid glamping experience. It has an outhouse, outdoor heated shower, and no cell or wifi service.

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.

Whole 2BD House – Spectacular Orchard Overlook!

Perched on a private hillside overlooking a valley of orchards, vineyards, and pastoral properties, this two-story home offers breathtaking views through expansive windows. The design blends rustic charm with modern comfort, featuring natural wood finishes, open-concept spaces, and wraparound deck and patio areas. Inside, enjoy a cozy living area with a wood-burning fireplace, a modern kitchen, and serene bedrooms for a restful retreat.

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.