Cottage vacation rentals in Grey Highlands

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Popular amenities for Grey Highlands cottage rentals

Cottage rentals with a hot tub

Superhost
An indoor hot tub is surrounded by wooden paneling and large windows that allow sunlight to fill the space. Natural stone accents and a serene greenery image on the wall enhance the calming atmosphere. Two wooden chairs are positioned nearby for relaxation.

Cottage in Kimberley

4.85 out of 5 average rating, 332 reviews

A Cozy Country Retreat *Indoor Hot Tub* Ski* Wi-Fi

NikaRating, 5 stars1 month ago
We had a relaxing and fun trip! David really created a whole experience and we enjoyed all the games and amenities they provided for us. We would definitely come back again!
Guest favorite

Cottage in Tiny

4.95 out of 5 average rating, 226 reviews

Private 40 Acre Cottage with Hot Tub

AntonioRating, 5 stars1 month ago
was great had a good time with my wife it was peaceful and private
Guest favorite
The exterior of a modern cottage is viewed, featuring natural wood accents and a blue siding. A spacious deck extends from the upper level, with tall windows allowing for ample natural light. Snow blankets the ground and evergreen trees frame the setting.

Cottage in Waubaushene

4.86 out of 5 average rating, 448 reviews

Charlie the Cottage | Hot Tub | Trail | Hike/Run

RiaRating, 5 stars6 days ago
Had a wonderful time at this charming cottage! It’s cozy, clean and has everything one needs for a relaxing getaway. The hosts were welcoming and provided excellent recommendations for local restaurants and activities. This is a perfect place to unwind and enjoy the quiet natural surroundings. Thank you for hosting us!
Superhost
A cozy outdoor space is surrounded by trees and autumn foliage, featuring multiple rustic seating options. Warm string lights hang overhead, illuminating the area. In the background, a serene view of the lake is visible, enhancing the peaceful atmosphere of the setting.

Cottage in Tiny

5 out of 5 average rating, 7 reviews

Lakeview Cottage

DavidRating, 5 stars5 months ago
We are so grateful for the absolutely perfect week we had at this beautiful, peaceful, well-appointed, comfortable cottage. The space was very clean, welcoming and bright, but cozy! We hope to return as soon as possible!
Guest favorite

Cottage in Coldwater

4.98 out of 5 average rating, 61 reviews

Cottage on the Rocks - with Hot Tub and Sauna!

ShivaRating, 5 stars3 days ago
We had a fantastic stay at the Cottage on the rock. Alex and David were excellent at communicating and were available to answer any of our questions. The cottage is beautiful, clean, tastefully decorated and cozy. We loved everything about this cottage and wish to come back again. Thanks again for your hospitality.
Guest favorite

Cottage in Innisfil

4.94 out of 5 average rating, 202 reviews

Utopia Villa and Spa

KellyRating, 5 stars1 week ago
This place was a great weekend getaway. Clean and quiet, lots to do. Everything you need and more. Check in was very easy and the host was extremely responsive and helpful. Would recommend and I'll probably be going g again myself :)
Guest favorite
Large glass patio doors frame a scenic view of the waterfront, revealing a private deck with seating and a hot tub surrounded by trees. Sunlight casts a warm glow over the area, enhancing the sense of tranquility.

Cottage in Innisfil

4.9 out of 5 average rating, 162 reviews

Stunning Lakefront Cottage Hot Tub & Sauna

GazalRating, 5 stars4 days ago
My team & I had a 2 day retreat together and love the space. We enjoyed the big windows, the sauna and the hot tub views. If you love nature and water, this place is a great option. The property was well equipped for kitchen needs. Kris was also very kind and accommodating and responsive. Can't wait to come back in another season!
Guest favorite
A modern kitchen is showcased with sleek white cabinetry and stainless steel appliances. A large island with bar seating is positioned centrally, complemented by stylish pendant lighting. The space is illuminated by recessed lighting and features a potted plant, contributing to a contemporary atmosphere.

Cottage in Innisfil

4.96 out of 5 average rating, 90 reviews

Relax & Entertain: Hot Tub, Sauna, Game room

MelissaRating, 5 stars2 weeks ago
We booked this property for a three family weekend away (with one day spent at the ski hill a half an hour away). The host was great to communicate with, the property manager as well. The place was clean, the bathrooms are beautiful and we used all the amenities and just had great family time. Exactly what we needed in our price range. My only comment would be that there wasn’t anywhere to hang towels so you might want to bring suction cups to hang them in the bathroom showers. Also, we brought firewood with us (although it was too cold to use the backyard fire pit). We did learn when we got there that the property manager has wood so save yourself the trip :)

Pet-friendly cottage rentals

Guest favorite
The exterior of the cottage is surrounded by a snowy landscape, featuring evergreen trees adorned with snow. A pathway leads to the entrance, and a picnic table is visible in the yard, creating a serene winter scene.

Cottage in Meaford

4.95 out of 5 average rating, 93 reviews

Woodski Winter Haven: Mountain Cottage Near Skiing

VeronicaRating, 5 stars2 weeks ago
We were so lucky to find this place available!! The property is very well maintained, it is very spacious and comfortable! Super fully equipped with everything that you need and more. We were very happy with our stay and with how attentive and responsive the host was. We highly recommend this place!
Guest favorite

Cottage in Coldwater

4.97 out of 5 average rating, 38 reviews

Charming 3BR Cottage on Tranquil Lake 🐦🛶🎣🏊‍♀️

KaiRating, 5 stars5 months ago
My group and I had an excellent stay at the cottage. The lake is beautiful and the property is as well; inside and out. The location is quiet, yet not too secluded, making the overall experience very peaceful. The home was also very clean, functional, and had even more amenities than we were even expecting! Definitely would visit again. Thanks Jenny and Bob!
Guest favorite

Cottage in Tiny

4.97 out of 5 average rating, 36 reviews

2 Bedroom Plus Bunkie Woodland Beach Cottage

JenRating, 5 stars3 months ago
Our family had an enjoyable Thanksgiving weekend at Carol's property. The cabin was cozy and charming, the bunkie was super cute and the deck and fire pit were amazing spots to hang out at. It's a short walk to the water and a convenience store/lcbo. Our only issue was that we didn't stay long enough!
Superhost
The cottage exterior features a large wrap-around deck furnished with outdoor tables and umbrellas. Lush greenery surrounds the area, contributing to a peaceful atmosphere. A stone pathway leads to the entrance, and firewood is neatly stacked underneath the deck.

Cottage in Tiny

4.94 out of 5 average rating, 142 reviews

Cozy 4 Season Family Cottage

HardikkumarRating, 5 stars3 months ago
Well, we loved the place. The cottage looks much better than it is in the pictures. We enjoyed inside, surrounding and fire pit. Anthony was very responsive and he let us stayed 1:30 hours extra on the checkout day which was extremely nice. Hoping to visit again in the summer 2025.
Superhost
A sun sets gently over a calm lake, casting warm colors across the sky. Two red loungers are positioned on sandy beach, offering a serene spot for relaxation. Verdant greenery borders the shoreline, creating a peaceful natural backdrop.

Cottage in Penetanguishene

4.83 out of 5 average rating, 29 reviews

3 Bdrm Family Cottage Private Beach, Thunder Beach

ElaineRating, 5 stars6 months ago
We absolutely loved the cottage it was perfect for our week at the beach. The beach itself was just steps away and was absolutely beautiful with calm,clear water and friendly neighbours. There is a strong sense of community in the area. We really loved the outdoor shower which was a family favourite. We will defiantly come back to this cottage again and again if we can.
Superhost

Cottage in Wasaga Beach

4.88 out of 5 average rating, 245 reviews

Cozy Riverfront Cottage Retreat with Dock / Ski

AlexRating, 5 stars1 week ago
We had a wonderful winter skiing getaway at this charming cottage. It’s well-appointed, spotless, and offers a beautiful view of the river. The 30-minute drive to Blue Mountain was convenient, and we loved the large yard for our dog and the peaceful neighbourhood for walks. The kitchen had everything we needed, and the baseboard heaters kept the space cozy and warm.
Guest favorite
The image features a dog playfully jumping in shallow water at the edge of a beach. The sun sets on the horizon, casting warm light across the sky and reflecting gently on the water's surface, creating a serene atmosphere.

Cottage in Tiny

4.88 out of 5 average rating, 41 reviews

Balm Beach Cottage: Hot Tub/GameRoom/more!

AllanaRating, 5 stars1 week ago
This cozy staycation was exactly what we needed! The kiddos LOVED the game room bunkie, and we loved the perfect view of them while relaxing in the hot tub!! We would come back again & again, especially looking fwd to enjoying the area more in the warmer weather !!
Superhost
A spacious backyard is featured, with a grassy area set up for outdoor games. Seating includes red chairs around a firepit. An umbrella offers shade over the dining area on the deck. Surrounding trees provide a natural backdrop to the cottage.

Cottage in Wasaga Beach

4.93 out of 5 average rating, 15 reviews

Suzy's Beach House - Monthly Rentals

TeddyRating, 5 stars8 months ago
We really enjoyed our stay, the cottage was really clean and loaded with all amenities needed. Would definitely stay again

Private cottage rentals

Guest favorite
A serene swimming pond is seen with calm, turquoise water reflecting the surrounding greenery. Bright red chairs are arranged on the sandy beach, offering a perfect spot for relaxation. Lush trees and a distant cottage provide a natural backdrop.

Cottage in Southgate

4.89 out of 5 average rating, 104 reviews

Thistle And Pine Cottage

AmberlynnRating, 5 stars3 weeks ago
Jaclyn's place is exactly what I needed. The place is private, serene, and felt so homey. It was a lovely break from he city. Will visit again. Thank you for hosting us.
Guest favorite
A wooden dining area features a round table surrounded by four wooden chairs. The kitchen showcases wooden cabinets, a stove, a microwave, and a refrigerator. Natural light enters through a window above the sink, enhancing the warm wood tones of the room.

Cottage in Wasaga Beach

4.96 out of 5 average rating, 267 reviews

GATED RESORT COTTAGE

LilyRating, 5 stars1 month ago
We stayed for a few nights during the winter months and it was amazing! My friends and I had so much fun and had no complaints. Everything was very clean and cozy, as well as the host was very kind, respectful, and responsive! Definitely would recommend.
Guest favorite
A quaint red cottage is highlighted alongside a rustic barn, surrounded by a wooden fence. Lush greenery and wildflowers accompany the structure, creating a natural setting. The areas are bathed in warm sunlight, enhancing the serene and secluded atmosphere of the property.

Cottage in Palgrave

4.99 out of 5 average rating, 207 reviews

Hockley valley, up country guest cottage

ChristineRating, 5 stars2 months ago
Fere and her family were fantastic, and the location is a beautiful sanctuary. Looking forward to connecting again soon. Merci!💓🕊✨
Guest favorite
The exterior showcases a modern cottage with a blend of stone and dark siding. A spacious deck extends from the upper level, surrounded by trees. A gravel pathway leads to an entrance, while natural landscaping features a grassy area and mulch landscaping.

Cottage in Coldwater

4.86 out of 5 average rating, 29 reviews

4 Season Private Cottage on Gloucester Pool

SoroushRating, 5 stars1 month ago
I had an amazing experience staying at this brand-new cottage! From the moment I arrived, everything felt fresh, modern, and thoughtfully designed. The space was spotless and beautifully decorated, with all the amenities you could need for a comfortable stay. The kitchen was fully equipped, making it easy to cook meals, and the cozy living area was perfect for relaxing.
Superhost
The cottage is set among lush greenery, featuring a wooden facade and a distinctive gabled roof. A spacious deck is adorned with an umbrella and outdoor seating, inviting relaxation. Nearby, a fire pit is positioned on gravel, surrounded by logs, enhancing the outdoor amenities.

Cottage in Creemore

4.76 out of 5 average rating, 401 reviews

Cottage on the Noisy River/Blue Mountain/Wasaga

JamesRating, 5 stars1 month ago
We spent a wonderful few days staying at Nikki's cottage. Despite the rainy weather, the cottage was warm and cozy, and in a great location just minutes from Creemore. It had everything we needed, and I'd love to stay again.
Guest favorite
An expansive view of a lake at sunset, where vibrant orange and pink hues reflect on the water's surface. A dock extends into the lake, featuring several chairs positioned for relaxation. Silhouetted trees frame the scene, adding to the tranquil ambiance.

Cottage in Severn

4.98 out of 5 average rating, 81 reviews

Severn Waterfront Cottage with breathtaking sunset

PatriciaRating, 5 stars6 months ago
We enjoyed everything about our stay! The location is beautiful with so many options to explore - canoe, kayaks and paddleboards, and also relax - indoor sitting area with a great view, back deck, dock and fire pit. The cottage is incredibly clean and comfortable with everything you need (and then some) provided. Highly recommend booking this cottage!
Superhost
A cozy cabin is nestled among tall trees, with a grassy area in the foreground. The cabin features a front porch with steps leading up to the entrance. A trampoline is positioned nearby, offering a playful addition to the outdoor space.

Cottage in Innisfil

4.64 out of 5 average rating, 22 reviews

Cozy 2 bdrm cabin steps from beach

LeeRating, 5 stars4 months ago
Second time staying at Rachel's- lovely cottage and a great location. Rachel was extremely helpful and easy to communicate with. Thanks again!
Superhost
A sandy beach area is framed by gentle waves and a calm blue lake. A fire pit made of stones is visible in the foreground, surrounded by sparse grass and a few trees. The sky is partly cloudy, adding a serene ambiance to the scene.

Cottage in Tiny

4.67 out of 5 average rating, 36 reviews

Gramma's Cottage : Strtt- 2024-060 Airbnb in Tiny

PatriciaRating, 5 stars6 months ago
Went to James's place for some well deserved R & R and we got it. Lovely location, great swimming, the sun was shining, sand was golden, water was perfect. All the amenities we needed. Great to sit by the fire at night and enjoy the sun set. Loved the outdoor shower.

Quick stats about cottage rentals in Grey Highlands

  • Total rentals

    80 properties

  • Nightly prices starting at

    $50 before taxes and fees

  • Total number of reviews

    3.2K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    50 properties allow pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Canada
  3. Ontario
  4. Grey County
  5. Grey Highlands
  6. Cottage rentals