Holiday rentals in Southwest Middlesex

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Top-rated holiday rentals in Southwest Middlesex

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A view from a window showcases a landscaped garden with lush greenery and a stone pathway. A deer is seen standing in a grassy area, while vibrant potted flowers are arranged near a wooden deck. A barbecue grill is visible on the patio.
Cottage in Port Stanley
4.96 out of 5 average rating, 56 reviews

July and August Bookings Open!

One bedroom on the main and an additional upstairs for up to 2 extra guests - same booking. Deck, sunporch, AC, fully equipped. Would suite mature and senior travelers. Lovely pond and private/quiet location. October to March is discounted for off season PLUS I will reimburse the Airbnb fee (in cash upon arrival if you book for a month)!!! Perfect home for snowbirds or someone wanting to see what Port Stanley is like before moving here. Municipality of Central Elgin Licenced and Inspected.

Top guest favourite
The charming cottage features a steeply pitched roof with decorative trim at the peaks. A spacious wrap-around porch is visible, framed by greenery and stone pathways, providing a welcoming entrance. Large windows and a central door add to the inviting façade.
Farm stay in Strathroy
4.84 out of 5 average rating, 298 reviews

Oasis Cottage Home of the Country

Beautifully restored cottage with a wrap-around porch. Bright, open concept with access to a full gourmet kitchen, living room, 80 acres of country setting, with a fire pit and BBQ on a peaceful sundeck. This spacious home is a great place for family reunions, retreats. getaways, bridal showers, small friends events. (Barn rental available as an option). We are a short 15 minute drive to Grand Bend Beach or you can enjoy our river frontage, ponds, and 4 kms of trails in the Carolinian forest.

Top guest favourite
The open-concept living area features soaring wooden ceilings and large windows that invite natural light. A modern kitchen with a white island counter flows into a cozy seating area, which includes a comfortable couch and coffee table, while soft views of the surrounding greenery can be seen beyond.
Cottage in Fingal
4.95 out of 5 average rating, 85 reviews

Private Lake Front Chalet- With Pickleball Court!

Welcome to our chalet, a beautiful sanctuary nestled amidst the forest and overlooking Talbot Creek. Outfitted with a unique blend of rustic charm and modern comfort, it's the perfect destination to slow down and make memories. With 3 bedrooms, 3 pullout couches and 2 separate living rooms, there's plenty of space to spread out and enjoy the space. Surrounded by birdsong and far away from the hustle and bustle of the city, this chalet is the perfect spot to getaway with friends and family!

Top guest favourite
A wooden deck surrounds the darkly stained exterior of the apartment, featuring two bright red adirondack chairs positioned beside a small table. Large windows allow natural light into the living space, while greenery from surrounding trees provides a sense of privacy.
Flat in Duart
4.95 out of 5 average rating, 330 reviews

Troll Hill

Beautiful country apartment located in a woodlot between Chatham and London. Apartment is detached from main house and has a spacious deck surrounding it overlooking the forest. It also has a small cabin for the second bedroom that is accessible from March to October. There is a large inground shared pool, outdoor sauna, yard and walking trails nearby for nature lovers. Apartment and cabin are fully furnished and both have Wi-Fi. It’s located about 15 minutes from Rondeau provincial park.

Top guest favourite
An open-concept living space features natural wood beams and a striking black accent wall. A round dining table is surrounded by four chairs, with a cozy seating area enhanced by a large beanbag. Decorative plants and stylish lighting fixtures add warmth to the environment.
Guest house in London
5 out of 5 average rating, 48 reviews

Stylish Private Loft | 1800s Farmhouse | Lake View

One-of-a-kind loft that sits inside a restored 1800s farmhouse with exposed beams, gas fireplace, and a sunroom with serene water view. Separate entrance, completely private unit — designed for the ideal getaway. King Endy bed with luxe cotton bedding, roomy bathroom with soaker tub. Nespresso, craft teas, induction stove. Hi-fi sound system, 55" 4K TV with Netflix and Prime. Sit/stand desk with Herman Miller chair. Minutes from the highway — peaceful, private, and unforgettable.

Guest favourite
A rustic kitchen area is shown, featuring wooden walls and a warm hardwood floor. Essential appliances include a microwave and a coffee maker. A small wooden cabinet holds condiments, and a countertop provides space for meal preparation. A fire extinguisher is mounted on the wall for safety.
Cabin in Ailsa Craig
5 out of 5 average rating, 22 reviews

Strathroy Country Cabins

Take it easy at this unique and tranquil getaway. Located on a country road, virtually no light pollution. Fireflies in abundance (in season). Air conditioned, heated, BBQ, bar fridge, coffee maker, microwave, deck, queen size bed, Bell Express Vu tv. 30 minutes to Grand Bend beaches/theatre and London. Upmarket restaurants nearby. ON MUNICIPAL WATER. Pets welcome (review our pet policy) Lucky guests get to see deer in the pastures. Ask about plane rides.

Top guest favourite
An alpaca is gently approached by a child in a green outdoor space, surrounded by trees. An indoor pool area is visible, featuring large windows that allow natural light to flood the space. An aerial view showcases the property layout, including gardens and a pond. A cozy fire pit area is highlighted, with seating arranged around the flames under glowing lights.
Guest suite in Ridgetown
4.94 out of 5 average rating, 180 reviews

Luxury Suite Private Indoor Pool Alpaca Retreat

Spacious, open concept suite located on the basement level of a 7400sf mansion. Private entrance with pool access and outdoor dining area with picnic table. Enjoy the beautifully manicured grounds with walking paths throughout and come say hello to our alpacas who you are able to interact with. Right next door is 75 acres of crown land with beautiful nature trails, where you can enjoy bird watching and hiking. Only 5 minutes from Ridgetown and Thamesville!

Top guest favourite
Home in St. Thomas
5 out of 5 average rating, 57 reviews

lost + found under the pines

Lost + Found is a sanctuary for deep rest and connection, nestled among towering pines. This private retreat blends peace and modern comfort—a cozy living area with smart TV and Starlink Wi-Fi, a full kitchen stocked with spices, tea, coffee, and essentials, a spacious bath with shower, washer/dryer, and a comfortable queen bed. Outside, enjoy the fire pit, Blackstone grill, electric barrel sauna, and free parking—come home to yourself.

Top guest favourite
A charming outdoor seating area is featured, complete with a round table and four black chairs under a bright blue umbrella. Lush greenery and colorful flowering plants surround the space, while a gas grill is positioned nearby on a small paved section.
Home in Plympton-Wyoming
4.98 out of 5 average rating, 52 reviews

Charming quiet country retreat.

Freshly painted, this spacious and serene guesthouse is the perfect countryside retreat. Conveniently located just off Hwy 402, it's a short drive to local wineries, breweries, markets, restaurants, and beautiful Lake Huron. Just 10 minutes from Crescent Hill Acres, it's ideal for wedding guests and special events. Explore nearby attractions or simply relax and enjoy the peace and quiet in your home away from home.

Top guest favourite
A modern studio space features a spacious bed with crisp linens and decorative pillows. A comfortable armchair sits next to a stylish wooden media console, housing a large television. Natural light fills the room through windows, with contemporary artwork adorning the walls.
Flat in Strathroy
4.98 out of 5 average rating, 135 reviews

Strathroy Studio “Boutique living at its best!”

Welcome to your boutique-style studio in Strathroy — spotless, stylish, and thoughtfully stocked for a stress-free stay. Enjoy a 65" smart TV, fast Wi-Fi, a well-equipped kitchenette with coffee, tea & snacks, and a spa-clean bathroom with fresh towels. With private entry, easy parking, and cozy touches like slippers and local tips, it’s the perfect spot to unwind, work remotely, or explore the area in comfort.

Top guest favourite
A hot tub is situated on a spacious deck surrounded by lush green trees, providing a serene forest backdrop. Nearby, a glass-top table with several chairs offers an inviting space for outdoor dining. Sunlight filters through the leaves, creating a calming atmosphere.
Home in Southwold
4.97 out of 5 average rating, 205 reviews

Nature Lover's Luxury Paradise

Nature Lover's Luxury Home in the woods. Creek's Edge Estate is a beautifully decorated home that is nestled on 10 acres of private woods. Minutes from London, ON this 4BDRM+3.5 BATH home sits next to some private hiking trails. Enjoy the sounds & sights of nature while relaxing in the hot tub. A beautiful escape for couples, families or groups looking to relax and recharge. Too many amazing amenities to list!

Top guest favourite
A historic century home is framed by majestic white pines and manicured gardens. The stone facade features large bay windows, allowing natural light to fill the interior. The surrounding greenery contributes to a serene outdoor setting, ideal for relaxation.
Flat in Strathroy
5 out of 5 average rating, 16 reviews

Apartment in Historic Home 1

Peaceful and centrally located, our century home built in 1872, is surrounded by majestic white pines and next to parkland. Step back in time with every piece of modern convenience you could ask for. This tranquil historic charm is not only perfect for a get away, but also for remote work where you can work and relax in the same place!Keep it simple at this peaceful and centrally located place.

Popular amenities for Southwest Middlesex holiday rentals

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  4. Middlesex County
  5. Southwest Middlesex