Vacation rentals with outdoor seating in Southampton

My husband and I had a wonderful stay at Amanda’s cottage. The place is fully renovated with a picturesque front porch and a private backyard space. The cottage is nestled in between others and you can barely tell given how peaceful the street is. Proximity to Wiarton is a plus if you’re wanting to go out for food or a coffee shop. Highly recommend the stay, and Amanda is very responsive if you have any questions or need recos! Would definitely come back.

very clean , well maintained and a cozy place to relax . The owners have been very thoughtful about what to keep in the house to make the stay comfortable and fun for the visitors. Our 6 yr old son had a lot of fun playing in the yard

Beautiful space and super responsive & accommodating hosts! The place looks exactly like the photos and was a really nice space to spend the week. The only thing I wish we knew ahead of time was that the neighbours are pretty close on all 3 sides so it does impact the privacy of the backyard at times!

A Perfect Waterfront Getaway: Cozy, Clean, and Family-Friendly with an Exceptional Host! Our stay at this Airbnb was absolutely wonderful! From the moment we arrived, we were struck by the waterfront location, offering serene views and a truly relaxing atmosphere. The home itself was very clean, which is always a top priority, and it was evident that great care is taken to maintain a spotless environment for guests. The helpful host truly made our experience exceptional. Communication was prompt and clear, and they went above and beyond to ensure we had everything we needed, whenever required. This level of hospitality significantly enhanced our stay. The well-equipped kitchen was a dream for preparing meals. It had everything one could possibly need, from essential cookware and utensils to a good range of appliances. We particularly valued how child friendly We highly recommend this place for anyone seeking a clean, comfortable, and welcoming waterfront escape with excellent amen

The listing description doesn’t justify how great the place is. It has all the amenities as well as a workspace. Julie is responsive and very accommodating, really enjoyed our stay and had a wonderful time.

Relaxed homelike cottage. Very well equipped and comfortable. Easy walk to downtown, waterfront etc

We had an amazing stay at Jane and Steve’s place! They were very warm and were always accommodating and ensuring our stay was going well. Jane even ensured we got to our trail start and end one day. Everything about the “loft” was comfortable, the banana bread was amazing and it felt like we were visiting old friends. Thanks so much for helping to make a rainy cold weekend enjoyable!

We had an amazing stay at Jess and Nate’s cottage! It was very clean and had everything we needed. The location is perfect, close to downtown as well as the lake! Definitely looking to book again next year!

I enjoyed a peaceful 2 weeks at this beautiful Airbnb! The setting is surreal surrounded by nature and a river! I had everything I needed and I enjoyed a few nights with a cozy fire in the wood stove. The bed and couches were very comfortable. The No Frills in Shelburne was a great grocery store nearby. Wendy was always very responsive and helpful. As clearly noted in the description, there is no cell service but not a big deal as there is wifi. I hope to be back again one day! A true gem!

Words can hardly capture the magic of Cathy’s BnB in Wasaga. From the moment we pulled into the driveway, we knew we were about to experience something special. This isn’t just a place to stay — it’s a destination in itself, a beautifully curated space that feels like stepping into the pages of an artist’s journal. The first thing that struck us was the atmosphere — peaceful, welcoming, and infused with personality. Every inch of the property is meticulously thought out and bursting with creativity. You can feel Cathy’s heart in every detail. It’s clear that this isn’t just a business for her — it’s a lifelong passion project rooted in artistry and hospitality. Cathy’s background in the arts and event world shines through in the most delightful ways. If you’re looking for something more than just a rental, if you want to stay somewhere that feeds your soul as much as it rests your body, Cathy’s BnB is it. Thank you so much for our stay!

We had a fantastic stay at Sarah's place. The surroundings were very peaceful and private, yet conveniently close to all amenities. We were in the area for a fastball tournament, and this accommodation was a much nicer option than a hotel or motel. We utilized the kitchen to prepare our breakfasts and dinners instead of eating out, and the living room was a comfortable space for us to relax in during the evenings. The bedroom was spacious, and the bed and linens were extremely comfortable. We would definitely recommend this place to our friends and family. Thank you for a great stay!

they had very clear instructions, didn't need to reach out to the host even once during our stay! very clean as well and has good air conditioning

Matt and shauna were marvellous hosts!! they were extremely responsive and very kind! The house was perfect! Exactly as described, right by the water, for a great price! The cutest place with a full kitchen which was greatly appreciated! The weather wasn’t great but nothing a great book and even better view couldn’t fix! It made the perfect destination for our girls trip! 1000/10 recommend staying with them if you can!

Well equipped and comfortable to stay in the place. Extremely clear instruction provided. We particularly appreciate interior space, it is spacious and warm. Bed linen is perfect!!

Carina’s place is a small gem - cozy, neat and beautiful with a wonderful backyard. The hosts are very responsive and helpful.

We felt right at home at the Evelyn Suites. We were in town for a wedding at the Mill and the location was walkable to the wedding venue. Also super close to all the amenities in town. We would definitely stay here again!

Neil’s place was perfect. Very clean and cozy. Just as described. Neil’s was very helpful and responsive in terms of directions and rules and things to do in the area. The area was very peaceful and not too far from the village if you’re driving. Would stay again

Our one night stay at Sabine’s was tremendous. The home is well appointed with plenty of space and easy walking distance to the village. Located in a second floor end unit, it’s a place you immediately feel comfortable in. There is a view of the slopes from the main room picture windows and a small deck area with muskoka chairs. There’s a sizeable fridge to store your beverages to drink while soaking up the views. There are two bedrooms on the main floor, and good sized master in the loft with king bed and en suite. Sabine was very communicative and left detailed instructions. Remote check in was a breeze. There is parking available. I would definitely recommend, and would definitely come back.

Bruce was super helpful and has a great place. Would highly recommend!

Susan was an amazing host! She was very responsive the entire trip, making sure check-in instructions were clear and easy. She also checked in during the stay to make sure we had everything we needed. The house was actually much larger than we expected and was well maintained. Although we only stayed there during the night, it had everything we needed and tons of space for my group. Highly recommend!

Absolutely Wonderful Stay! I had an amazing stay at John and Kristi’s condo! From the moment I arrived, everything was spotless, cozy, and thoughtfully equipped with everything one could possibly need for a comfortable stay. The attention to detail made it feel like a home away from home. The pool and hot tub area were a real bonus—clean, relaxing, and perfect after a day of exploring. I definitely made the most of it! The location was also ideal, just a pleasant 10-minute walk to the village, which made it easy to enjoy the local shops, restaurants, and atmosphere without needing to drive. John and Kristi were fantastic hosts—friendly, responsive, and clearly committed to creating a great guest experience. I would absolutely stay here again and highly recommend it to anyone visiting the area!

Leo and Josie were great! They were friendly and responsive and made sure we had everything we needed for our stay! There were 6 of us and we all had more than enough space. It was a great stay, would definitely recommend! :)

This place was beautiful! As soon as we walked in, we felt at home. All the amenities listed were in the property and in good condition. Richard was very helpful and responsive when we had questions for him. There were extra pillows for people who sleep with more than just one lol. The ceiling fan in the loft really cooled down the place and kept the place at a good temperature. The area is also lovely, with a nearby tennis court on the resort. My friends and I spent most of our time there playing pickleball and tennis. Also, Blue Mountain village is about a 20 minute walk from the resort, so my friends and I went to visit at night. Overall, this was a lovely place to stay for the weekend and I would definitely come back again!

Kadri’s place is lovely, with many extra well thought out details provided. And communication with Kadri was excellent. It’s a lovely neighbourhood and so close to the trails, golf restaurants. The water and close to skiing. You won’t find a nicer place to stay while in Collingwood.