
Vacation rentals in Southwold
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Top-rated vacation rentals in Southwold
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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.
4.99 out of 5 average rating, 117 reviews
Cute Cottage steps from the Main Beach
Built in 1919, this charming beach house is a Port Stanley original! Although updates have changed this cottage over the last 100 years, my historic cottage is the perfect blend of charm, comfort, and convenience. Located on a dead end street and directly across the road from the main beach, the location is ideal for exploring all the harbour has to offer. During the summer, a separate guest house with private bathroom is included, accommodating up to 8 guests total. Winter: up to 6 Guests
4.93 out of 5 average rating, 114 reviews
New Home Sleeps 14, 6BR, BBQ, Games Room, Office
6 Bedrooms Near London, ON New 3400 sqft furnished designer home in the family neighborhood of Talbotville with convenience and comfort in mind! House has large private, fenced yard and backs on to a public park with playground, bball court, and soccer field. All new appliances and furniture. Includes spacious front office with doors for privacy, Fully stocked kitchen, 2 living rooms equipped with TV and PS3, Games Room, highspeed WiFi, and 4 bathrooms ensure a comfortable and relaxing stay.
4.97 out of 5 average rating, 158 reviews
5 of 5 Luxury Suites in Mitchell Heights Building
Welcome to Mitchell Heights(Suite 5)! A unique building, rich in history with 5 luxury suites. Beautiful views of a picturesque ravine. Come alone or rent multiple Suites with with family/friends. Couch fits 1 adult or 2 kids. Full kitchen, bedroom, laundry, dishwasher & toiletries, linens, towels etc. Hang out on the deck and enjoy BBQ or fire 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.
4.76 out of 5 average rating, 45 reviews
Orchard Beach Boutique Cottage
**See note on guest maximum** Century cottage with floor level changes between rooms on main floor - watch your step! 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 max of 4 adults over 12, as per local municipal license** please follow our license rules, ask if you aren’t sure. Pet-friendly, well-appointed cozy cottage steps from beach, shops and dining, with parking for 4 in the driveway.
4.99 out of 5 average rating, 183 reviews
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!
5.0 out of 5 average rating, 100 reviews
Newly renovated cottage on large private beach
Kick back and relax in this freshly renovated beach retreat. This property was recently taken back to it's studs and fully updated to lakeside luxury for you to enjoy. Sip your morning coffee from the gazebo on your private beach and spend your evenings roasting marshmallows by the fire to the sound of the crashing waves. We aim to provide you with a resort-like, turn-key experience. STR License Number: twenty twenty five - eleven - twenty one - zero zero nine
4.99 out of 5 average rating, 87 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, cozy hammock, Blackstone grill, electric barrel sauna, and free parking—come home to yourself.
5.0 out of 5 average rating, 70 reviews
Port Talbot White House- With Pickleball Court!
Beautifully renovated 6000 square foot home nestled amongst the trees of the Port Talbot Estate. The White House has it all! A private Lake Erie beachfront (shared only with the other 2 cottages on the property,) endless hiking trails, beautiful cliff bluffs and a winding creek that's perfect for a morning canoe ride through the forest. Converted riding arena is now home to 2 pickleball courts as well as ample room for activities!
4.98 out of 5 average rating, 124 reviews
Luxury 5BR· Chef's Kitchen · Sleeps 10 · Superhost
⭐ Superhost · 100% Response Rate New build, 2024 · 3,500 sq ft of designer luxury for up to 10 guests · London, Ontarios finest estate home in prestigious Silver Leaf Estates. Whether you're planning a family reunion, corporate retreat, graduation celebration, golf getaway, or Western University visit — this is the only home in London, Ontario that delivers resort-calibre space, finishes, and hospitality at an Airbnb. .
4.8 out of 5 average rating, 84 reviews
My Mom's Cottage
Have fun with the whole family at My Mom's Cottage located in the Kokomo Beach Club in Port Stanley! This incredible home is yours to enjoy in a brand new space. Minutes away from the beach and all the best Port Stanley has to offer! Enjoy the luxury amenities provided while getting an opportunity to enjoy small beach town vibe! There is something in Port Stanley for everyone! Beaches, Dining, Golf, Nature and more!
4.96 out of 5 average rating, 72 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!
4.97 out of 5 average rating, 216 reviewsPopular amenities for Southwold vacation rentals
Other great vacation rentals in Southwold

The Barntreat Sauna and Plunge
4.8 out of 5 average rating, 10 reviews
Blue dreams at Port Stanley
4.91 out of 5 average rating, 23 reviews
Courthouse District Cozy Getaway
4.92 out of 5 average rating, 48 reviews
The Sunbeam Cottage in the heart of P.S.!
4.92 out of 5 average rating, 60 reviews
Stunning Newly Constructed Home in Port Stanley
4.8 out of 5 average rating, 45 reviews
Fall and Winter in Port Stanley
4.97 out of 5 average rating, 67 reviews
Bright*Laundry*75"TV*Sleeps10*Patio*Parking*Wifi
5.0 out of 5 average rating, 4 reviews
Sunnyside Beach House in Kokomo 7 beds 10 guests
4.92 out of 5 average rating, 61 reviewsDestinations to explore
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