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Tailwinds B&B

3.0 star property
Sip coffee by the firepit as you plan your day of discovery. Relax amidst natural beauty at this charming bed & breakfast.

Choose dates to view prices

Near Hillsburgh Library, Tailwinds B&B offers a cozy retreat with full breakfast, shopping on site, and a firepit. Connect to in-room WiFi or unwind in the garden with outdoor furniture; additional perks include luggage storage and a TV in the lobby.

Reviews

9.8 out of 10
Exceptional

Popular amenities

  • Parking included
  • Free WiFi
  • Air conditioning
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Property amenity
Cheltenham Suites
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  • Parking included
  • Free WiFi
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9.2 out of 10, Wonderful, 119 reviews
The price is CA $159
CA $180 total
includes taxes & fees
May 21 - May 22
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Policies

Check-in

Check-in start time: 3:00 PM; Check-in end time: 10:00 PM

Minimum check-in age: 18

Check-out

Check-out before 11:00 AM

Special check-in instructions

There is no front desk at this property

Guests will receive key retrieval information

A virtual front desk provides assistance to guests

Information provided by the property may be translated using automated translation tools

Access methods

Key retrieval, private entrance

Pets

Pets not allowed

Children and extra beds

Children are welcome

Free rollaway/extra beds

Property payment types

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards and debit cards; cash is not accepted
Safety features at this property include a fire extinguisher

We should mention

This property does not have elevators

Frequently asked questions

Is Tailwinds B&B pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Tailwinds B&B?

As of May 20, 2026, prices found for a 1-night stay for 2 adults at Tailwinds B&B on Jun 14, 2026 start from CA $165, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Self parking is free at this property.

What time is check-in at Tailwinds B&B?

Check-in start time: 3:00 PM; Check-in end time: 10:00 PM.

What time is check-out at Tailwinds B&B?

Check-out is at 11:00 AM.

Where is Tailwinds B&B located?

Situated in a rural location, this bed & breakfast is 0.2 mi (0.4 km) from Hillsburgh Library and within 12 mi (20 km) of Forks of the Credit Provincial Park and Belfountain Conservation Area. Island Lake Conservation Area and Cheltenham Badlands are also within 16 mi (25 km).

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

Reviews

9.8

Exceptional

10

Cleanliness

9.6

Amenities

10

Staff & service

9.8

Property conditions & facilities
Rating 10 - Excellent. 63 out of 71 reviews
Rating 8 - Good. 8 out of 71 reviews
Rating 6 - Okay. 0 out of 71 reviews
Rating 4 - Poor. 0 out of 71 reviews
Rating 2 - Terrible. 0 out of 71 reviews

Reviews

Verified

10/10 Excellent

Mikala.

Liked: Cleanliness, amenities, property conditions & facilities
Amazing place to stay and incredible hospitality. Food was also so delicious! Great hosts, highly recommend !
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Blaire

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We love it here. Room is beautiful and the breakfast is amazing. Happy we came back and would love to come back again.
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

Nathan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This place was fantastic! Trev and Janet the friendliest hosts you could ask for. The rooms were great, breakfast was amazing. We will definitely go back.
Stayed 1 night in Mar 2026
Verified

10/10 Excellent

marilyn

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Big beautiful room with en suite, and the breakfast was great!
Stayed 2 nights in May 2025
Verified

10/10 Excellent

Edward

Liked: Cleanliness, amenities, property conditions & facilities
Room is clean and comfortable and host is friendly. Breakfast also was good, we finished most of the food.
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Amazing breakfast as usual! Cozy rooms. Quiet and comfortable
Stayed 1 night in Dec 2025
Verified

10/10 Excellent

christos

Liked: Cleanliness, property conditions & facilities
The room was tastefully done, very comfy bed, and Janet makes an amazing breakfast!
Stayed 1 night in May 2025
Verified

10/10 Excellent

Grace

Liked: Amenities, property conditions & facilities
Lovely spot. Great breakfast. Will stay again.
Stayed 1 night in Jun 2025
Verified

10/10 Excellent

Jennifer

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Thanks so much for a great stay! The space is beautiful and breakfast was delicious!
Stayed 1 night in Apr 2025
Verified

10/10 Excellent

Kimberly

Liked: Cleanliness, staff & service, property conditions & facilities
Great 1 night stay with super friendly hosts! Breakfast was tasty and hearty. We will stay again when down in the area!
Stayed 1 night in Jul 2025
Verified

10/10 Excellent

Lijun

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Lovely homemade breakfast in the morning in a beautiful house! Very accommodating and friendly staff. Would recommend staying here if you’re exploring trails or parks.
Stayed 1 night in Aug 2025
Verified

10/10 Excellent

Lilli

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My husband and I had an absolutely wonderful mini-vacation here! The bathroom was downright luxurious - though shared, which did make for some uncertainty - and the breakfast was delicious. Overall, we had a very relaxing time staying there, everything felt clean and organized, and the property and surrounding areas were gorgeous. Very much recommend!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, property conditions & facilities
Nice house, well kept, in country setting. Nice staff and also enjoyable and good breakfast.
Stayed 1 night in Aug 2024
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Amazing place

Everything was amazing, very clean and comfortable The area was covered in snow, very pretty Next time I would love to stay longer! We loved here!
Stayed 1 night in Dec 2024
Verified

10/10 Excellent

Sharel

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Perfect place to unwind and take in the serenity of the peaceful and tranquil setting. My best friend and I loved it and we're certainly returning. My dog loved it too!
Stayed 1 night in Jun 2025
Verified

10/10 Excellent

Jackie

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Would stay again!

A beautiful stay! We felt very taken care of. The check-in/out process was casual and simple, as we were arriving later. The home was cozy and tidy. The breakfast was delicious. I wish we could have stayed longer to check out more of the property and surrounding area.
Stayed 1 night in Jul 2025
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Incredible bed and breakfast experience

Everything about this stay was perfect, from the welcome note upon arrival to the cleanliness and comfort of the room, to the beautiful views and delicious breakfast. The hosts are wonderful and responsive and made for one of the best bed and breakfast stays I’ve ever had. Would look forward to returning here again anytime!
Stayed 1 night in Mar 2025
Verified

10/10 Excellent

Cheryl

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The accomodations were excellent, beds were super comfortable, bathrooms were very large and clean, house was very nice. We opted for the express "to go" breakfast as we had to leave a bit early, and it was still amazing!!
Stayed 1 night in Sep 2024
Verified

10/10 Excellent

Trevor

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Tailwinds is the model of a B&B. The hosts, Janet and Trevor, provide stellar comfort, amenities, and service. It’s a beautiful property, with a lot of places to relax and chill. Tailwinds is a short walk to Hillsburgh and the locals are friendly! We’ll definitely be back!
Stayed 4 nights in Jul 2025
Verified

10/10 Excellent

Marcos

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The place was beautifully decorated and makes you feel at home, very quiet and peaceful. Janet makes sure everything is right for you. Everything is clean and organized. The breakfast is fantastic. A place you must try.
Stayed 2 nights in Aug 2025
Verified

8/10 Good

Amanda

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Beautiful place, the hosts are lovely. Breakfast was delicious too. Only issue we had was the shared bathroom.
Stayed 1 night in Sep 2024
Verified

10/10 Excellent

Kathleen

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great place to stay!

It was very clean and comfortable. Breakfast which was included was fresh, filling and delicious. The owners are fantastic people! The area is beautiful with a view of the pond and the trees changing colour.
Stayed 1 night in Oct 2024
Verified

10/10 Excellent

Ashleigh

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
My husband (and our friends) all had an amazing stay. The owner was accommodating and SO friendly. We are already planning another stay together next year.
Stayed 1 night in Dec 2024
Verified

10/10 Excellent

Carolina

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Was and amazing experience everything is amazing, the bed is very comfortable, the view outside i stunning, the rooms have everything you need the decoration are very personal. Breakfast was incredible, I asked for and early breakfast and the made me a breakfast to go. Was incredible. Exced my expectations. I will definitely come back.
Stayed 2 nights in Oct 2025
Verified

8/10 Good

TC

Liked: Cleanliness, staff & service, property conditions & facilities
There is a hiking trail nearby!!
Stayed 1 night in Nov 2024