Vacation rentals with outdoor seating in Ashland County

This cozy cottage is such a nice stay! It is in a great neighborhood, and the neighbors are so kind and friendly and helped us shovel the driveway when we had snow during our trip. The house was so clean and cozy and had everything we needed- coffee, games, books, a snow shovel, Tupperware, plastic wrap, and even candy bowls. We felt right at home and will definitely be back!

We felt right at home! The house was comfy and perfect for our weekend getaway! We are already talking about making another trip soon!

This home is a true beauty! The owner has created a lovely oasis with a keen sense of style. Everything was so homey and comfortable. We especially loved cooking in the well-appointed kitchen - top notch! The upstairs great room made us feel like we were in a light and bright treehouse despite being in the woods. It was hard to believe we were just minutes from downtown Ashland. Thank you, thank you for sharing such an amazing home with us (and will you come decorate our house, pretty please?)!!

Our entire family enjoyed Bay Top Lake house. Beautiful surroundings - coffee on the dock, lunch and dinners on the deck and star watching at night. Private yet close to Bayfield for easy access to Madeline Island and Apostle Island tours. Monica is a wonderful host - great communication and the house had many thoughtful touches. Would give Monica and the home a ten if possible!!!

We love Bayfield and the Chequamegon Bay area, and Willard House was a perfect jumping off point. A quick walk down the hill to Lake Superior, shops and restaurants (do keep in mind it's a decent uphill back to the house for those who may have issues walking). The house was well-appointed and clean, and the hosts were sure to reach out to us multiple times to check in during our stay. Bonus points for allowing dogs. We would definitely stay here again!

Very happy with our accommodations .The kids really enjoyed the two game tables and the adults enjoyed large table and kitchen areas for entertaining

My stay was absolutely wonderful! Karen was incredibly kind and proactive, providing clear and helpful instructions well in advance, which made check-in and navigating the space a breeze. The apartment itself was spotless and well-maintained, offering a comfortable and relaxing environment. Best of all, the location was perfect—within walking distance to everything I needed, from shops and restaurants to local attractions. I would definitely stay here again and highly recommend it to anyone visiting the area.

This was a great house to stay at, plenty of space and amenities. We did not really use the basement but it was nice to have the extra space available. It was nice that they now have a Weber gas grill, we made good use of it. Great central location to explore the a Apostle Islands and the UP.

This is a totally lovely place! And the hosts are super wonderful. Reserve it now! 😁

Ewelina’s place was the perfect setting for a quick weekend in nature. Ewelina was incredibly responsive and helpful. This cozy apartment was spotless upon arrival, comfortable, and was stocked with more than I could ever need. The attention to detail was evident; I cannot recommend this place enough.

My husband and I enjoyed our stay at Hillside Suites. It was in a perfect location, close to restaurants, shops, and the Ferry to Madeline Island. We were able to effortlessly ride our bikes to the ferry dock & hop on the ferry. Our room was a comfortable retreat after long days of adventuring around Bayfield. Our on-site host was very helpful in recommending places to see & things to do. She even shared a plate of freshly baked cookies with us on a rainy day. Our room was well stocked with everything we needed & more. The outdoor patio with beautiful flowers made the outside a tranquil spot to relax. We loved our stay!

Great place and our family had a really good time. Great location to be able to ski in and out and the wood stove was a nice touch. The house was hard to find in the dark when we first arrived and price seemed a little steep for what it was. Overall nice place and we would recommend.

We spent the holiday weekend here celebrating my parents 60th birthday. The place was clean, cozy, and in a great location. Walkable to everything and nice that it had its own parking spot. The were extremely responsive to any questions/concerns we had and were very accommodating. We would definitely stay here again and would recommend it to anyone looking for a getaway to Bayfield!

This is a great space for a group! The pictures don't clearly show how spacious it is. Plenty of room to make meals, lounge, relax in the sun room, etc. It's right off a hiking trail and has beautiful views. Very close to town and walking distance to a delicious little bakery.

Erin's place was clean, comfortable, and well-appointed. It's in a lovely, wooded setting and located near the quaint lakeside town of Bayfield. I only stayed a couple of nights, but the unit has all the amenities needed for a long stay. Highly recommended!

Felt very comfortable in this quiet, lovely neighborhood with great hosts. The hilly streets made me think of San Francisco a bit so we used our car even to go downtown where parking was not a problem. Highly recommend St James Social for Sunday brunch and delicious coffee specialties. Don’t miss the spectacular Dobson Garden across from the Brownstone Trail by the marina. Also, music dockside while enjoying fish & chips at Hoop’s is a must. Madeline Island has a fabulous beach so allow time for this. If you take the Apostle Island cruise, avoid sitting by the water’s edge topside if you want to hear the captain’s narration! Sorry to miss the lighthouse tour. We came too early in the season. So glad we visited Bayfield & surrounding area!

Excellent condo beautiful surroundings great weather very good trip

This was our second stay here. The hosts are helpful and responsive. We were so comfortable and the place is so central. We love it!

Great little condo in a fantastic location! We loved the lake view and how close it was to many amenities. Would definitely stay here again!

This was a great place to stay for our end of the season ski trip. A close 2-minute walk to the chalet. There is a lift even closer, but it wasn't running, presumably because our stay was the last weekend of the ski season. The condo was clean, tidy, and had everything we needed. Beds were comfortable and cozy. Myron was super helpful and responded to messages within minutes. Being April, it wasn't cold enough to warrant using the hot tub, but it looked great. He offered to let us check out later since the cleaning crew wasn't arriving right at 11:00. Much appreciated! So much nicer to change in his condo rather than the chalet before our drive home. Looking forward to booking this condo again for our annual Michigan ski trip next winter!

We stayed during a snowstorm that dumped a foot of snow and Wendy made it really easy to add an extra night to the stay

The apartment was actually nicer in person than we had anticipated from the pictures. The location was very convenient and within walking distance of almost everything in LaPointe. The member of our group who had lived in New Orleans especially appreciated the Cajun seasoning left in the cupboard!

We loved this place, very close to big Powderhorn, snow river and ironwood. The price was great considering how expensive lift tickets have gotten. A hot tub out back would make this place perfect!

We really enjoyed our stay. The condo was just as she described it and it was a homey stay for us while we enjoyed a weekend of skiing. We really liked having a fire in the evenings and there was space for us to dry our clothes from the day. The only bummer was having people stay above us. The floors were very creeky, but ear plugs helped with that while sleeping. Overall, we were happy with our choice to stay here and would definitely do it again.