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BEST RATED ORANGEVILLE, ON BED AND BREAKFAST

3 Best Bed and Breakfasts in Orangeville, ON

Expert-recommended Top 3 Bed & Breakfasts in Orangeville, ON. All of our B&Bs actually undergo a rigorous 50-Point Inspection, which includes everything from checking reviews, ratings, reputation, history, complaints, satisfaction, trust and price - all to ensure overall excellence. You deserve only the best!

Orangeville bed and breakfast Molly's Retreat Bed and Breakfast
Orangeville bed and breakfast Molly's Retreat Bed and Breakfast
Orangeville bed and breakfast Molly's Retreat Bed and Breakfast
9+ YEARS IN TBR
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MOLLY'S RETREAT BED AND BREAKFAST

(5.0 Score)
28 Riverside Drive, Mono,
Orangeville, ON L9W 6L4 Directions

Specialty:

✓ Daily Housekeeping ✓ Fax/Photocopying ✓ Swimming Pool ✓ Shared Lounge/Television Area ✓ Special Diet Meals ✓ Ironing and Concierge Service ✓ Heating ✓ Secured Parking ✓ Baggage Storage ✓ Bottle Of Water ✓ Garden ✓ All Spaces Non-Smoking (Public and Private) and Terrace ✓ Air Conditioning ✓ Breakfast ✓ TV LCD ✓ Wi-Fi Service

“Molly's Retreat Bed and Breakfast has a cozy and comfortable B&B that is ideally situated near seven major wedding venues. The property is a smoke-free and pet-free property, and offers on-site self-parking. The B&B amenities include a wraparound deck with an above-ground swimming pool, a jacuzzi tub, private en-suite baths in each room, free wireless internet access, and a full homemade breakfast. They are delighted to advise that they now offer REIKI sessions at their venue. The concierge services, including theatre ticket and spa booking assistance at Hockley Valley Resort or the Millcroft Inn, are available. They can recommend restaurants and interesting places to visit in the area. They accommodate specific dietary requirements.

2025 Update: Eileen and Sam are the hosts of the B&B. The dining room is always open, and you are most welcome to enjoy a delivered meal there.”

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Price:

Molly's Suite (King Room) + HST $285br> Alena's Suite $210
The Foster Suite $210

Contact:

(519) 942-0256

Check-in time: 3pm
Check-out time: 11am

TBR® Inspection Report:

Orangeville bed and breakfast McKitrick House Inn
Orangeville bed and breakfast McKitrick House Inn
Orangeville bed and breakfast McKitrick House Inn
Orangeville bed and breakfast McKitrick House Inn video
4+ YEARS IN TBR
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MCKITRICK HOUSE INN

(4.9 Score)
255 Broadway Avenue,
Orangeville, ON L9W 1K6 Directions

Since 1887

Specialty:

✓ Guest Rooms ✓ Fireplace ✓ Air Conditioning ✓ Bathrooms ✓ Royale Suite ✓ Bridal Suite ✓ Four Poster Canopy Bed ✓ Original Claw Foot Soaking Tub ✓ Comfortable Seating Area ✓ Terrace & Cable Television

“McKitrick House Inn has a beautiful Victorian home furnished with antiques from that period and is located in Historical Downtown Orangeville, Ontario. They have five comfortably appointed guest rooms; three rooms feature ensuite bathrooms. McKitrick House Inn's bridal suite includes a queen-size four-poster canopy bed, a fireplace, and an original clawfoot soaking tub, creating an unrivalled ambiance. McKitrick House Inn is an ideal venue for intimate special events. This traditional B&B, set in an antiques-filled Victorian home, is 9 km from Alton Mill Arts Centre and 19 km from Mono Cliffs Provincial Park.”

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Contact:

(519) 942-3602

Check-in time: 1pm
Check-out time: 11am

TBR® Inspection Report:

Orangeville bed and breakfast Tailwinds B&B
Orangeville bed and breakfast Tailwinds B&B
Orangeville bed and breakfast Tailwinds B&B
6+ YEARS IN TBR
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TAILWINDS B&B

(4.8 Score)
17 Station Street, Hillsburgh,
Orangeville, ON N0B 1Z0 Directions

Since 2016

Specialty:

✓ Laundry Service ✓ Air Conditioning ✓ Family Rooms ✓ Fireplace ✓ Non-Smoking Rooms ✓ Baggage Storage ✓ Bathrooms ✓ Clock Radio ✓ Robes ✓ Cot Available ✓ Slippers ✓ Hairdryer ✓ Toiletries ✓ Bottled or Filtered Water and Writing Desk ✓ Bottled or Filtered Water ✓ Writing Desk ✓ Wi-Fi ✓ King Size Bed ✓ Cot ✓ Shared Bathrooms

“Tailwinds B&B has rooms featuring air conditioning, a clock radio, robes, slippers, a hairdryer, toiletries, bottled or filtered water, and a writing desk. They offer friendly accommodations and a relaxing atmosphere for guests’ pleasant stay. Tailwinds B&B's breakfast menu includes nuts, granola, berries, yogurt, and more, with organic fruits and vegetables being a staple. Their beverage menu features a variety of juices, teas, and coffee. Tailwinds B&B is an ideal location for outdoor adventures, including cycling, hiking, running, horseback riding, snowshoeing, cross-country skiing, and snowmobiling on nearby trails. The B&B is located just 13 miles away from downtown Orangeville.

2025 Update: The property offers a paid airport shuttle service for your convenience. Each unit at the bed and breakfast is equipped with bed linen and towels. They prioritize sourcing local products, with Everdale Organic Farm being their main supplier, located just around the corner. Tailwinds B&B also features three fire pits on the property, providing amenities such as battery-operated lanterns, Thermacell units to repel bugs, and lighters to start fires. Weekly and monthly rates are available.”

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Price:

Century Room: Single Occupancy $150
Additional Person $15
Gran Fondo Room: Single Occupancy $130
Additional Person $15 Spring Classic Single Occupancy $150
Additional Person $15

Contact:

(519) 855-3242

Check-in time: 3pm
Check-out time: 11am

TBR® Inspection Report:

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MOLLY'S RETREAT BED AND BREAKFAST REVIEWS

All I can say is wow! We just spent a fabulous weekend as guests of Eileen and Sam, the proprietors of Molly's Retreat. Our room was beautiful, spacious and spotlessly clean (as was the whole house), breakfast was top-notch and the warmth and hospitality received from our hosts was incomparable. The house is in a quiet location meaning we got an excellent night's sleep but just a few minutes drive from great places to eat and lots of local attractions. We are already looking forward to our return. Thank you Eileen and Sam.

We stayed for an evening while attending an engagement in town and thoroughly enjoyed our stay at Molly's Retreat Bed and Breakfast. Eileen and Sam were very warm hosts, the rooms were immaculate and well kept, and the property is very peaceful. Their breakfast was 10/10 and something you would expect from a fine dining establishment. Would definitely recomend for a short or long stay.

Our time at Molly’s Retreat was just fantastic. They welcomed us as if we were family. Our room was immaculate - the attention to detail exceed that of any hotel we’ve been to. You can really tell they care about their guests. The breakfast was also delicious, the fruit salad was to die for. Molly’s Retreat felt like a home away from home, I will most definitely be coming back!!

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MCKITRICK HOUSE INN REVIEWS

I stayed here for awhile and I have to say this was the best BnB I've ever stayed at, Great Breakfast in the morning if you want it, amazing location, Beautiful astetic for the house amd the garden, Lovely Staff who live on site and are super friendly, Very affordable, Clean rooms and common areas, Perfect location for starting a site seeing tour, Perfect for Honeymoons, Perfect for singles and partners, Perfect for the whole family. And The best homemade jams from the houses grandma are just to die for, I highly recommend staying at this beautiful location in downtown Orangeville.

Great place with a wonderful owner. We called in last minute and she accommodated is. Very hospitable and friendly. The house itself is very charming with lots of personal touch and a great garden front and back. If I had to be a bit critical though, the bed sheets could use freshening up. But over all a great stay for us.

This place has to be the friendliest place I've stayed at. The rooms are clean and fully stocked. The staff are amazing. I would 100% recommend this place to stay to anyone I know. Thank you forbthe amazing stay.

TAILWINDS B&B REVIEWS

This bed and breakfast was the best experience I’ve ever had. It was so clean, cozy, simple check in and the grounds are stunning. Has its own little pond with a looking station and Trevor and Janet do a fantastic job at making you feel at home but also in your own little oasis. The calmness that this place brings is incredible. I stayed with my husband for anniversary weekend and went to the spa for a full day, if I had to choose between going to the spa again or staying here I would 100% choose staying at tailwinds for longer instead of going to the spa. Great job at keeping this B&B so well kept. I would recommend this to anyone ! Can’t wait for our next visit.

I reserved Tailwinds for my wedding guests. Trevor was wonderful and absolutely incredible to work with. He was very accommodating. He went above and beyond to ensure my guests were comfortable. They even shuttled them to the event! I can't thank them enough for their hospitality! Our friends all had wonderful things to say about their stay and they loved their breakfast.

This was our second time staying at Tailwinds B&B and it was just as wonderful as the first time! Janet and Trevor were so great, beautiful property, comfy bed, delicious food (they accommodated for vegan food and it was delicious)! Won't hesitate to stay here again!

TBR® Inspection Score Report

MOLLY'S RETREAT BED AND BREAKFAST Total Inspection Points: 119/120
Complete Info: 9
Acknowledgments: 10
Business Images: 10
Contact Info: 10
Current Evaluation: 10
Exact Services: 10
Experience: 10
Legitimate Ratings: 10
Pricing: 10
Reviews Accuracy: 10
Website Source: 10
Website Standard: 10

TBR® Inspection Score Report

MCKITRICK HOUSE INN Total Inspection Points: 118/120
Complete Info: 9
Current Evaluation: 9
Acknowledgments: 10
Business Images: 10
Contact Info: 10
Exact Services: 10
Experience: 10
Legitimate Ratings: 10
Location Proximity: 10
Reviews Accuracy: 10
Website Source: 10
Website Standard: 10

TBR® Inspection Score Report

TAILWINDS B&B Total Inspection Points: 115/120
Experience: 8
Acknowledgments: 9
Complete Info: 9
Current Evaluation: 9
Business Images: 10
Contact Info: 10
Exact Services: 10
Legitimate Ratings: 10
Pricing: 10
Reviews Accuracy: 10
Website Source: 10
Website Standard: 10

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