Vacation rentals in Southwold

Stunning harbour front suite w/ exceptional views.

Sit back, relax, and watch boats pass by from The Bridgeway, a beautifully renovated suite in the heart of Port Stanley Village. Ideally situated beside Kettle Creek and the historic Lift Bridge, it’s steps from shopping, entertainment, marinas, award-winning restaurants, and a short, scenic harbour walk to Port Stanley’s beaches. This bright, spacious suite features a large open-concept living/kitchen area with one-of-a-kind panoramic views overlooking the harbour — the perfect spot to unwind.

1 of 5 Luxury Suites in Mitchell Heights Building

Welcome to Mitchell Heights(Suite 1)! A unique building, rich in history. 5 luxury suites with beautiful views of a picturesque ravine. Come on your own, or rent multiple Suites with with family & friends. 4 people Suites also available. This Suite has a full kitchen, toiletries, linens, towels. Hang out on the deck and enjoy a fire or BBQ your dinner with your travelling companions, all while listening to the sounds of nature. 8 minute walk to Erie Rest Beach and the town is just down the road.

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.

Charming Village Loft Getaway

Step into a storybook scene at the Village Loft in charming Port Stanley. Nestled above a delightful candy store and next to an iconic ice cream shop, enjoy sweet aromas and scents from high-end restaurants nearby. This newly renovated two-bedroom loft in a historic building combines modern amenities with cottage charm. Steps from restaurants, a local market, shopping, art galleries, the harbour, and a quick walk to the beach. Experience history, charm, and comfort! Book your stay today!

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.

The Sunset Chalet is in a Quiet neighbourhood.

WELCOME to Sunset Chalet. We have had a make over! See and hear the nature at the front and back. You may get a view of the many deer,fox and wild turkeys that frequent this quiet neighbourhood. From the hilltop you get a partial view of water and pier.Hear the fishing boats as they pass to go into Port to unload their catch (the action starts around noon). Port is full of excitement: enjoy the theatre, public library, many coffee shops, restaurants, taverns, and Beaches.

Orchard Beach Boutique Cottage

**See note on guest maximum** Your family will be close to shopping, dining and fun when you stay at this home that’s hidden away, while in the center of everything. **Guest maximum of 4 does not include children under the age of 12, as per local municipal license approval** please help us adhere to our license rules, ask if you aren’t sure. Pet-friendly, well-appointed cozy cottage steps from the beach, shops and restaurants, with plenty of parking in the driveway.

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.

Olive Branch Inn No.2

Welcome to Oliver Branch Inc. 2 — Your Peaceful Getaway A beautiful and spacious home where comfort and calm meet. Nestled in a quiet neighborhood, it offers a serene and welcoming atmosphere — perfect for work, rest, or a weekend escape. Ideally located just 15 minutes from London, 10 minutes from Highway 401, and 20 minutes from both Port Stanley and Port Bruce. Explore charming beaches, local shops, and scenic country roads.

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.

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!

The Executive Hideaway: St Thomas Serenity

The Executive Nest-Your St. Thomas escape: Stylish two bedroom apartment for professionals, seeking comfort and calm. Enjoy a fully equipped kitchen, high-speed Wi-Fi, and a serene space for work or unwinding. Steps from shops, dining, and other amenities, this modern retreat blends productivity with get away vibes. Welcome to your Executive Nest, where relaxation and efficiency meet in perfect harmony.