Vacation rentals in Bailieboro

4.93 out of 5 average rating, 263 reviews

Cottage in Brighton

Bianca Beach House - EV/Hot Tub/Firepit/Waterfront

AlexRating, 5 stars4 days ago

Everything about this cottage is perfect. The host thoughtfully provided everything for a great stay. The kitchen is fully equipped—just bring your food. Views from the living room and bedrooms are breathtaking, overlooking the lake with beach-like waves. If it rains, you have board games, vinyls, video games, and a big TV with streaming services by a cozy fireplace and charming decor. Outside, the beach is right by the deck—perfect for morning coffee and peaceful moments. There’s a spa, BBQ, and a fire pit for romantic sunsets. Kayaks are available in the basement; bring your fishing gear (and permit). This is our favorite place so far. It’s walking distance to a waterfront trail and Presqu’ile Park amazing hiking trails, places to picnic, etc by the lake. You’re close to shops and great diners like Counter in Trenton and Whistling Duck in Brighton. This last-minute trip turned into an amazing find. Huge thanks to Jess, our host! We can’t wait to be back.

4.97 out of 5 average rating, 65 reviews

Cottage in Havelock

Waterfront Magic! on Round Lake.

LoRating, 5 stars1 week ago

Incredibly beautiful surroundings, right on the lake. Private and plenty to do with lake watching, kayaking and walking. The house was spotless, simple, comfortable and welcoming, great for a family of four. The fireplace and windows in the main bedroom were gorgeous. Kara and Serge were very friendly and helpful. We’ll be going again.

5 out of 5 average rating, 17 reviews

A calm lake reflects the surrounding trees and the evening sky. A cozy lodge is visible with warm lighting, situated on the shore. Various watercraft, including kayaks and paddle boards, rest on the sandy beach, inviting outdoor activities.

Cabin in Trent Lakes

Luxury Cabin On 100+ Acre Sandy Beachfront Lake!

BrianRating, 5 stars6 months ago

"Our stay at Jesse’s place was exceptional from start to finish. Jesse was incredibly responsive and attentive, answering all of our questions almost immediately and going above and beyond to make our stay comfortable. The house itself was exactly as described—beautifully designed with multiple relaxing areas to enjoy the breathtaking views. One of the highlights was sitting outside by the fireplace, overlooking the lake, which made for a truly magical experience. The entire house was impeccably clean and well-maintained. Jesse's hospitality and helpfulness made our visit truly unforgettable. We highly recommend staying here!"

4.92 out of 5 average rating, 60 reviews

A backyard oasis features a sparkling pool surrounded by lush greenery. Colorful inflatable floats are arranged on the water. Comfortable seating areas are provided under a wooden structure, enhancing the relaxation space. Vibrant flowers and potted plants complete the tranquil outdoor setting.

Bungalow in Lindsay

The Perfect Retreat-Heated salt water pool

AliRating, 5 stars8 months ago

Pat’s home was a perfect spot for our girls weekend. The heated pool and patio was beautiful, the beds were comfy and the living space and kitchen were perfect. Pat was friendly in our conversations and always quick to respond to question. We’d come again! Thank you Pat!

Cottage in Kawartha Lakes

A wooden dock extends into clear water, featuring vibrant red lounge chairs positioned for relaxation. The shoreline is bordered by smooth stones and gentle waves, with lush greenery in the background enhancing the natural setting.

4.95 out of 5 average rating, 165 reviews

Balsam Brilliance, Modern Lake Home.

RainaRating, 5 stars3 weeks ago

Such a gorgeous property and stunning views! The main living area had views from both south and north views of the lake since it is on a point. Stocked with everything we needed. Was a lovely weekend to honour my late uncle with my family. Balsam lake was his favourite spot. We went up the weekend after the huge ice storm so the place was running on a generator, which actually stopped working for a bit but the owners were on top of it as soon as they heard. They were very helpful. Would definitely stay there again in nicer weather! 🙌🙌

4.98 out of 5 average rating, 64 reviews

A scenic view showcases the cottage set back from the water, surrounded by green lawn and trees. A wooden dock extends into the water with a small boat and pedal boat anchored nearby, providing access to the serene lakeside.

Cottage in Hastings

Rustic Cozy Cottage|Waterfront, HotTub, Wood Stove

BarbaraRating, 5 stars2 weeks ago

My husband and I - and our dog - were looking for a quiet, comfortable escape from the city and we found it at Dmitry’s cottage! It was absolutely beautiful with everything we needed including a magically lit hot tub, high end amenities and a lovely view with a surprising number of birds that live in the area. We were even able to spot an eagle’s nest and its occupants :) Dmitry was so accommodating and easy to communicate with, offering an early check in as well as an offer to extend our stay which we were more than happy to accept!! We would definitely recommend Dmitry’s cottage and look forward to returning for another city escape.

4.83 out of 5 average rating, 47 reviews

A charming red cottage is set along the lakeside, featuring a spacious deck with colorful chairs. A boat is docked at the private pier, and lush greenery surrounds the area, reflected in the calm water. The overall scene conveys a tranquil lakeside atmosphere.

Cottage in Douro-Dummer

Nordic Spa Getaway on Stoney Lake

RebeccaRating, 5 stars1 month ago

We really enjoyed our stay at Ken's place. We stayed during a pretty nasty ice storm so it was incredibly helpful that we had the back-up generator. His maintenance guy Bill was great at checking in with us and making sure everything was working as expected.

4.92 out of 5 average rating, 60 reviews

A serene view of a marina features multiple boats docked on calm waters, surrounded by lush greenery. Red adirondack chairs are positioned around a picnic table, creating an inviting outdoor space. The clear blue sky enhances the tranquil atmosphere of the waterfront.

Cottage in Harcourt

Modern Yellow Cottage Harbourtown Marina

AutumnRating, 5 stars8 months ago

We’ve been staying at Jessica’s properties for the past four years and always enjoy our stay. If you have a boat or other water vessel, this place provides a free slip for the duration of your stay which is great! Jessica’s properties are always extremely clean, free of clutter and provide all the necessities and more! The restaurant and general store at the marina (on site) are very convenient. If you do have a boat or rent one on site, be sure to visit Juniper Island! It’s always a fav of ours to visit.

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Popular amenities for Bailieboro vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Bailieboro

5 out of 5 average rating, 11 reviews

A wooden dock stretches out over calm waters, featuring two chairs positioned side by side. A small table sits between them, with a vase of flowers enhancing the serene lakeside scene, surrounded by blue skies and distant tree line.

Cottage in Lakefield

The Lakehouse on Cedarwood

KarenRating, 5 stars7 months ago

Our group enjoyed a late summer weekend at this beautiful cottage. Everyone loved it! The kitchen is so well equipped with proper pans, utensils, and an array of spices. It was so clean inside and felt very homey. Meagan was super easy to communicate with. Our dog loved the shallow lake entry. Can't wait to be back in the future :)

4.99 out of 5 average rating, 100 reviews

A wooden dock extends over calm waters, surrounded by lush greenery. The sky is partly cloudy, casting gentle reflections on the surface of the river. The scene is serene, highlighting the natural beauty of the waterfront.

Cottage in Peterborough

Beautiful Waterfront 5 Bedroom 4 Season

BennyRating, 5 stars7 months ago

This was our third year staying at Paul’s beautiful spot on the river. As a group of seven seniors this spot is extremely suitable for our needs to be on one level. A perfect place for a larger group. Thank you Paul for letting us enjoy your clean, easily accessible home for our holidays. Hopefully see you next year.

4.94 out of 5 average rating, 157 reviews

Cottage in Brechin

Spacious waterfront cottage w/ spectacular sunsets

EstellaRating, 5 stars3 months ago

Definitely recommend this cottage to everyone my family and I had an amazing time it was so beautiful I love the scenery especially in the winter wow 20x more gorgeous it was awesome, lot of thing to do, the fire was so nice! Really love this place definitely will be returning!! Dave was amazing host!! Thank you Dave for everything!!

5 out of 5 average rating, 8 reviews

A two-story terrace features a wooden deck furnished with four turquoise chairs arranged around a patterned area rug. Lush greenery and distant trees are visible in the background, under a bright sky with scattered clouds.

Home in Baltimore

Summer Getaway with Pool and Nearby Attractions

EmilRating, 5 stars7 months ago

Had a great stay at Eva's place. Eva was very responsive in answering us and also very clear with instructions. The house was kept neat and tidy and location was calm and peaceful. When propane has was out, she was kind enough to get a new one as a replacement. Highly recommend for anyone/family for a weekend getaway. Thanks you Eva for letting us stay at your place.

4.88 out of 5 average rating, 127 reviews

A two-story cottage is seen set against a backdrop of trees and a gentle slope. A wooden staircase leads up to a spacious outdoor deck, furnished with colorful chairs. Surrounding greenery adds to the natural ambiance, while the ground is covered in fallen leaves.

Cottage in Brighton

Spacious 3+2 BR 2Bath Cottage w/ FirePit & PoolTbl

GabrielleRating, 5 stars1 week ago

A wonderful stay. The clearing was very private and the inside was as beautiful as a chalet. we had a small child with us, and I was pleasantly surprised with how safe it was for him to be here.

Vacation home in Havelock

A wooden dock extends over calm waters, two black adirondack chairs are positioned to face a vibrant sunset reflecting on the lake. Surrounding trees frame the scene, creating a serene environment ideal for relaxation.

4.94 out of 5 average rating, 16 reviews

Spacious Waterfront Year Round Cottage

DavidRating, 5 stars6 months ago

Jen's place was a perfect venue for a get together with some old friends. We enjoyed the camp fire, sat on the dock, and took a walk on the nice trail that's just a short walk away. The cottage had everything we needed. Thanks for a great weekend!

4.76 out of 5 average rating, 17 reviews

A spacious living area features a light gray sectional sofa adorned with yellow accent pillows. A wooden staircase ascends along the wall, while the adjacent kitchen area is visible in the background. The flooring provides a warm contrast to the light-colored walls.

Home in Pickering

Cozy Stay Away From Home

NicoleRating, 5 stars16 months ago

I really enjoyed my stay at Thurinaas! She was prompt on communicating in regards to the booking. It was very clean and comfortable! The bed was also very comfy too! I would definitely stay here again!