Vacation rentals in Southwest Middlesex

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Top-rated vacation rentals in Southwest Middlesex

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Guest favorite

A spacious wooden deck extends from the home, featuring outdoor seating arrangements including two chairs and a table. Potted flowers add color to the edges, while a charcoal grill is positioned nearby. Views of the serene lake and surrounding trees create a calm outdoor atmosphere.

Cottage in Port Stanley

4.95 out of 5 average rating, 92 reviews

Stunning Cliffside Lakeview Home on 1.3 Acres

Sweeping landscape is the background for serenity at this stylish home; a picturesque view of the lake, outdoor fire pit, charming forest, small man-made pond & plenty of deer sightings. Screened-in gazebo w/ outdoor dining table & plenty of outdoor seating incl. lounge set. Inside boasts 2 bedrooms & sunroom w/ 2 pull-out couches w/ lake views. Finished bunkie with a full bathroom available for over 6 guests . Walkable to Little Beach, 7 min drive to Big Beach. No beach access from property.

Superhost

A spacious balcony is adorned with comfortable seating and a round fire pit on a wooden deck. The railing provides a clear view of the lush landscape leading down to the lake, with trees lining the edge and cloudy skies above.

Cottage in Port Stanley

4.93 out of 5 average rating, 69 reviews

Look out over Port Stanley Main Beach

Situated along the hilltop of Port, this cottage offers guests sweeping views and summer vibes like no other! Just a short walk from the beach, this cottage has been completely renovated to a high standard, and makes a great spot to soak up the sun with friends and family alike. Trust us, you’ll have enough space for all your vacation needs. Port has so much to offer visitors to our sunny town, including a soft sand beach, charming shops, a selection of restaurants, and exciting nightlife.

Guest favorite

An open living area features a cozy chair and a matching ottoman beside a small wooden table. The kitchen, with dark cabinetry, is visible in the background, while a bar area with high stools invites casual dining. Natural light floods through the large windows.

Cottage in Lakeshore

4.93 out of 5 average rating, 69 reviews

Cottage in Lighthouse Cove with Canal Docking

Stunning fully furnished cottage on the water great for any get away. Gorgeous updated floors recently completed on the home. Located at Lighthouse Cove, offers lots of entertainment with a pool table game room and tons of space. Dock your boat on the canal in the backyard for the weekend with access directly to lake St. Clair or the Thames River. Easy access to a private boat launch down the road and a private beach foot steps away. Enjoy kayaks provided and beautiful sunsets at night

Guest favorite

Cottage in Plympton-Wyoming

4.84 out of 5 average rating, 107 reviews

Cottage Cliff Beach

Our property is double wide with panoramic Lake View. Access to the beach via a new public stair case 7 cottages down. No direct access from our property. We do not have neighbours either side. We are located in a friendly quaint community. A good mix of seasonal cottages and full time residence. The panoramic view is seen from two of the 3 bedrooms. Imagine waking up and from the comfort of your bed enjoying the sights and sounds of the endless lake horizon. Please be our guest!

Top guest favorite

A wooden deck features swings overlooking the lake, with colorful chairs positioned nearby. A stone fire pit sits surrounded by outdoor seating, complemented by the serene lake view and grassy area that extends towards the water.

Cottage in Leamington

4.99 out of 5 average rating, 305 reviews

It's a 'Shore' thing - Executive Retreat

Year round beautiful upscale 3 bedroom modern, chic cottage. sleeps 6. Outstanding views of lake. Relax in the Hot tub, Gas fireplace for cool nights. Outdoor gas fire table. Fabulous for romantic getaways, GIRLS 'just wanna have fun' weekends, or friends gathering .Beach/boat launch in walking distance. Gas BBQ, central A/C, wifi. Even swings overlooking the lake!! Great area for Wineries, Birding, Fishing, sightseeing, Pelee Island, Conservation areas. EV outlet on property.

Top guest favorite

Home in Grand Bend

5 out of 5 average rating, 41 reviews

The Sandpiper Grand Bend Beach

Discover the ultimate Grand Bend vacation rental just steps away from the famous beach, restaurants, bars, & shopping! This stunning brand-new home features four king beds, a built-in bunk, pull out couch, 3.5 bathrooms, a game room, balcony, backyard deck with BBQ and fire table. Perfect for multiple families or groups! Enjoy quality time together watching movies, playing ping pong or gathering around the fire table. Book your stay today and create unforgettable memories!

Top guest favorite

Home in Grand Bend

4.96 out of 5 average rating, 25 reviews

Top of Grand Bend

Enjoy truly immaculate accommodations in this sparkling BRAND NEW riverfront beach pad just a 4 minute walk to Main Beach & fronting the Parkhill creek as it flows into the Ausable. Experience why Grand Bend is the #1 beach town in Ontario in a stellar location that is literally steps to everything you'll need, including our world famous blue flag beach & fishing in your backyard. Professionally designed & set up by Grand Bend Real Estate Inc, this is the spot to be!

Guest favorite

A modern black cottage is showcased against a clear blue sky. A spacious deck is visible with decorative flower pots at the entrance. The surrounding landscape features trees, adding to the inviting appeal of the property.

Cottage in Grand Bend

4.97 out of 5 average rating, 100 reviews

Lakeside Beach House Grand Bend-prime location

BEST location possible! Perfect family cottage or girls getaway! Take in the world famous Lake Huron Sunsets while soaking in the hot tub under our huge covered patio (w 65inch tv in summer) Beautifully furnished & completely renovated. WIFI, Netflix, Air con. Glass showers. Washer/Dryer. Cosori Air fryer. BBQ. Keurig pod machine & reg coffee maker. Parking for 8 cars. 50 STEPS from Main Street. Follow us @lakesidebeachhouse for cancellation and availability updates

Superhost

Cottage in Bluewater

4.91 out of 5 average rating, 114 reviews

Lakefront Cottage Rental - With Private Beach!

Newly renovated luxury lake front cottage! Enjoy the views of the best sunsets from the backyard. Private Beach access! Beautiful modern farmhouse style living space. Two fully renovated washrooms with Marble tile throughout. Comfortably sleeps 8! Don't miss out on an opportunity to enjoy this beach and these views. Please be advised price includes additional cleaning fee to adhere to CODVID cleaning protocol and properly disinfect cottage upon each check out.

Guest favorite

A serene outdoor space overlooking the lake features a concrete patio with a fire pit at the center. Wooden chairs are positioned nearby, complemented by large rocks along the water's edge. A staircase leads to a deck, providing access to the stunning lakeside view.

Cottage in Leamington

4.95 out of 5 average rating, 150 reviews

Sunrise Retreat - Lakefront Cottage w/ Hot Tub

This beautiful tranquil cottage is the perfect escape from your everyday frenzied life. Perfect for a couple's getaway, girls’ weekend or just a space to be on your own. Located on a quiet road, close to beaches, walking trails, fishing harbour, restaurants, wineries & breweries. Well behaved dogs are welcomed. Renters must be over the age of 30. Annual Family Pass to Point Peele National Park is available for all guests to use.

Guest favorite

A serene outdoor space is illuminated by soft blue lights surrounding a hot tub, creating a tranquil atmosphere. A patio heater stands nearby, providing warmth against the snowy backdrop. The entrance to a cozy building is visible, adorned with gentle winter lighting.

Apartment in Port Franks

4.94 out of 5 average rating, 165 reviews

Romantic Studio Cottage w/Hot Tub, Sauna, Gym

Private entrance, hiking trails, 5 minute drive to beach. ADULTS ONLY Luxurious Studio Apartment, Kitchenette, breakfast bar, sitting area, sofa, fireplace, Netflix, king canopy bed, private deck, private bathroom. Shared amenities (hot tub & sauna) are booked directly with your hosts to ensure guests privacy, open 10 am to 12 am daily. Smoke free property inside (smoking permitted at fire pit only) No Pets allowed

Guest favorite

Cabin in Lambton Shores

4.95 out of 5 average rating, 127 reviews

Mid Century Modern 5Br Sleep 10 Southcott Retreat

Peaceful - quiet setting Mid Century Modern Grand Bend Retreat, *NON SMOKING* Mid Modern Scandinavian Design Vacation Home in Southcott Pines, Outdoor screened room, 2 decks, easy access to beach and strip, WIFI, 65" TV, 55" TV, Natural Gas BBQ, 6 burner gas stove, onsite laundry, Central Air, fun loft bedroom, large lower sectional, rotating and recliner chair, shallow sand beach. Bring your beach towels and sunscreen!