Family-friendly holiday rentals in Southampton

Hand-Crafted Cabin in Stunning Beaver Valley

Lovingly designed and built tiny house in the heart of the beautiful Beaver Valley. 2 Double beds, small kitchenette, rustic deck & living area with a gorgeous outhouse. The property has extensive edible landscapes & greenhouse filled with seedless grapes & edible perennials. Beautiful views of the escarpment, close to the Bruce Trail & Beaver River access point for canoeing and kayaking. Shop at the achingly charming Kimberley General Store. Close to Blue Mountains, Thornbury & Collingwood

Secluded 1200' beachfront private 64 acre log home

Welcome to Dragonfly Cove Our log cottage features: *1200 feet of BEACH FRONT *Family-friendly, romantic, retreat *64 private forested acres, secluded cove on Lake Huron *Sleeps 10 (8 adults +2 children on futon) *Full view of lake & sunsets from spacious deck *Full kitchen with antique stove/oven combo *Stunning large glass sunroom *Central AC+heating *Gas+wood fireplaces *Bruce Tel internet *6 person hot tub *Firepit *2 kayaks *3000 acres of manicured trails at McGregor Point Provincial Park

Family Cottage close 2 everything room 4 everyone!

Large common spaces and lots of natural light make this a comforting space. Backing on to wooded trails, walking distance to everything, come and enjoy a slower more relaxed pace of life. At the beach, at the tennis club, on the river, in the woods, or in town. Or just hang with your favorite people on the deck, the screened poarch or around the big table. With heightened awareness of cleaning and safety we follow Airbnb’s enhanced cleaning protocol, which was developed with expert guidance.

Quiet Retreat for Two

Spend a starry night in the country with the comfort of a soft bed, a wood stove, and plenty of space both indoors and out. Our yurt is located in a pocket of trees next to rolling farm fields and beautiful conservation land that the Rocklyn creek meanders through. You can prepare your meals in a sweet outdoor kitchen that is entirely screened in- or choose to sit by the fire. Bruce Trail access is just around the corner, and the towns of Meaford and Owen Sound are a short scenic drive away.

Holiday House on Huron

The location is truly special—just a short walk to boutique shops, local cafés, excellent restaurants, and a craft brewery. Whether you're here for the beach, biking the scenic Saugeen Rail Trail, or exploring the charm of small-town life, this is the perfect spot to experience it all. The open concept upper level is designed for gathering, entertaining, or simply unwinding in comfort. Main floor, you’ll find three cozy bedrooms (primary bedroom with ensuite), a full bathroom with bathtub.

Cabin Suite #6 at Driftwood Haus

Pet Friendly! Listen to the waves steps away! All newly renovated with brand new beds and furnishings. Enjoy the freedom. With the second best sunsets in the world according to National Geographic, Southampton is a community on the shores of Lake Huron in Bruce County, Ontario, Canada and close to Port Elgin. It is located at the mouth of the Saugeen River next to the Saugeen Ojibway Nation Territory. We have the most beautiful public beach in Ontario, a natural harbour and 3 lighthouses!

Spa cottage: hot tub, sauna, cold plunge & firepit

Open plan bright cottage with Scandinavian inspiration including mid century modern furniture. Walk to beaches, bike trails and picturesque downtown (brewery, restaurants). Great for Fall hiking (Bruce Peninsula) and Winter snow shoeing and ice skating (McGregor provincial park) Go to an OHL game (Owen Sound), golf or yoga class. Outdoor spa: 7 person hot tub, 6 person sauna, cold plunge tub and fire pit. Pizza oven. Indoors: Fast wifi, table tennis and two fireplaces (natural gas)

The Nest at Victoria Street

Welcome to The Nest! This sweet, cozy 1-bedroom self-contained suite is part of a gorgeous century home in the heart of Southampton. Located one block from the main street, walking distance to downtown shopping, restaurants, parks, hiking, swimming as well as the best small town ice cream parlours. Directly across the street is a playground & splash pad for the kids. Enjoy a cocktail & BBQ on your private deck. Come relax & treat yourself to a vacation in our lovely beach town.

Pine Villa-Mediterranean Cottage with Hot Tub

Escape to our charming Mediterranean-inspired villa nestled in the serene countryside of Ontario. With minimalist aesthetics, the cottage offers a tranquil retreat for relaxation. Immerse yourself in the natural beauty that surrounds as you unwind on the patio or in the hot tub, or explore the countryside with our complimentary bikes. Inside, enjoy minimalist design, cozy details, and a nostalgic record player—where modern comfort meets rustic charm.

The Clubhouse - Welcome to Port Elgin, Ontario.

A true BEACH TOWN experience! The Clubhouse in PORT ELGIN has: - Beautiful private backyard with firepit, upper and lower decks - 4 bedrooms w/ queen beds - 2 full bathrooms - 3 parking spots - 8-person dining and games table - foosball table - a home theatre w/ Netflix You will be: - 10 min WALK from Port Elgin beaches, downtown shops & pubs - 90 mins from The Grotto (Tobermory) - 40 mins from Sauble Beach No smoking, pets or parties please.

Forest Dome

This is an air b&b you'll definitely remember. Experience the magical feeling of waking up among the trees and birds. Feel the exhilaration of taking an outdoor shower. Enjoy the crackling fire and take the time to dream again. Nature, art, waterfalls and trails are all just outside your doorstep. Try our available snowshoes to explore even further! You don't want to miss this peaceful retreat.

Dushi Beach House, Prime Southampton Location

Southampton Beach House is ideally located to take advantage of everything the area has to offer. Blocks to the beach, one block to High St (Southampton's Main St) and all of the great shops and restaurants. I purchased this 100+ year old house in Southampton in February 2021. From top to bottom the house was renovated and is basically brand new with all new furnishings.