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Vacation rentals with a pool in Grey County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Grey County

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Home in Chatsworth

4.89 out of 5 average rating, 141 reviews

Stonehaven - large country retreat, with pool*

Situated on 100 acres of grass, field and forest, this easy-access property has miles of trails, in-ground pool (not heated), huge lawns, beach volleyball, fire pit, tubing run, and lots of space indoors - 5 rooms on the main level, 6 bedrooms upstairs. >> Borders OFSC trail Ideal for multi-family groups looking for a great country getaway, it is one minute from the major highways coming from Toronto & Guelph towards Owen Sound. We offer full-week discounts. (Please note firm pool closing dates)

Condo in The Blue Mountains

4.93 out of 5 average rating, 269 reviews

Cozy Studio Mountainside stay in Blue Mountains

Fall colours will arrive soon at Blue. Book your getaway now. This cozy STUDIO ground floor condo is perfect for a couple/small family (Max 4). The unit includes: a comfy queen bed and a pop up sofa bed, bathroom with jacuzzi tub, electric fireplace and full kitchen with everything you need. Free parking. Pool and two shared hot tubs are open daily until October. Tennis courts and access to hiking trails. The Blue Village is only a 5 minute drive away with great local restaurants and shops.

Home in Meaford

4.96 out of 5 average rating, 160 reviews

Redhill Luxury Home...by the Blue Mountains

This eco friendly house of 4,500 sq ft is bright, modern, luxurious on 50 acres of rolling hills with a beautiful pond and hiking trails. All bedroom ensuite plus two extra full bathrooms. Comfortably sleeps up to 24 guests. Amazing view, sunset and star gazing. Salt water pool in the summer. Outdoor BBQ, fire pit, Hot Tub year round. Minutes to Christie beach, ski hills, golf courses, Bruce Trail. Enjoy snowshoeing, cross country. Serenity on top of the hill! See more info under the space.

Home in Desboro

4.97 out of 5 average rating, 119 reviews

Forest Loft - Forest, Sauna, Ponds & Stargazing

The “Forest Loft” is a one-of-a-kind space surrounded by the old-growth trees of Kinghurst Forest. The 1,600-square-foot space sleeps up to four and features two Queen-size beds and linens, huge harvest table, indoor kitchenette with a stovetop and fridge, filtered water, shower, propane and wood stove heating, in-door basketball hoop, hammock, picnic table, a commercial grade BBQ, fire ring and access to two beautiful spring-fed ponds. Access to Finnish sauna for four is available on request.

Condo in The Blue Mountains

4.87 out of 5 average rating, 200 reviews

Northern Peaks - Ski in / Ski out

Northern Peaks is an updated loft located in North Creek Resort at the North Base of Blue Mountain. Ideal location for those seeking easy access to the ski hills and hiking trails but still within minutes to Blue Mountain Village. North Creek resort offers a free shuttle service to Blue Mountain Village, an outdoor swimming pool open in the summer months, two hot tubs year round, tennis courts with night lights, charcoal grills and community picnic tables that you can use during your stay.

Home in Owen Sound

4.98 out of 5 average rating, 223 reviews

The Butchart Estate: your perfect family retreat!

Looking for a special place to spend some time? Make Butchart Estate your own, self-contained and private family retreat. Share precious time together and make some memories in this beautiful and well-equipped heritage home. Inside, enjoy the gourmet kitchen, relax in your own private indoor pool & hot tub, curl up by the fireplace, play board games galore. Free wifi. Outdoors, explore our beautiful nature walks, and local excursions. Enjoy a slower pace, and treasure some time together.

Townhouse in The Blue Mountains

4.85 out of 5 average rating, 204 reviews

Happy Valley Retreat at Rivergrass

Our condo at Rivergrass sleeps 8 and is located in the heart of Blue Mountain, just minutes from the best golfing and hiking trails in Ontario. Take in the view of the 18th hole at Monterra from the back deck or spend time at the pool and hot tub. Our fully stocked condo includes all linens, kitchen necessities, a BBQ and an outdoor locker to store your golf clubs. Automated self check-in upon arrival and we are available 24/7 to answer any questions you have. STA LicenceLCSTR20220000126

Tiny home in Meaford

4.86 out of 5 average rating, 311 reviews

Tiny Home Nestled between Thornbury & Meaford

Tiny home situation 10 min to Thornbury and 10 min to Meaford, and 20 min from Blue Mountain Village, nestled a country/residential area. Has all the basic comforts including spacious 3 piece bathroom. Close drive to beaches and many hikes and cross country ski trails in the area. It is also a 15 minute drive from Beaver Valley Ski Club and a number of different cideries. Shared heated pool available for the summer months. INTERNET just upgraded! Window Aircon unit for main floor added.

Place to stay in The Blue Mountains

4.83 out of 5 average rating, 530 reviews

Base of the Mountain, 2 Bedroom Loft Condo.

This newly updated, clean ski chalet is a lovely 2 bed 2 bath, at the base of Blue Mountain. Our chalet is one of the few units that has a private first floor bedroom. The location is a great jumping off point for all the activities you can enjoy at Blue Mountain, Collingwood and Georgian Bay. Blue Mountain Village, as well as the Scandinavia Spa , Northwinds Beach, cafe's and restaurants only 1Km away. Ski In/Ski Out with the north ski lift approximately 150 meters from our unit.

Farm stay in Markdale

4.99 out of 5 average rating, 133 reviews

Experience Country Living at Firefly Ridge

Your private living space is comfortable and bright, with lots of picturesque windows and high ceilings. There is a walkout to a private area where you can relax, and unwind, enjoying the sounds of nature and some farm animals, such as horses, minis, donkeys, goats, chickens, cats, 2 Australian cattle dogs and even some piggies. We love our animals and we welcome yours as we are a pet friendly farm. PLEASE NOTE DOGS MUST BE ON A LEASH WHILE ON THE PROPERTY.

Rental unit in The Blue Mountains

4.96 out of 5 average rating, 194 reviews

Studio at Blue-KingBed/HotTub/Shuttle/Ski In&Out

Welcome to our studio unit in the mountainside North Creek Resort! *King bed *sofa bed-double sized memory foam mattress *SMART TV, High-Speed Rogers Ignite WIFI and TV *Cookware, Utensils and Keurig *freshly painted *remodeled washroom Property Features: *Shuttle Service *Year Round Hot Tub *Seasonal Pool *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing) STA License #LCSTR20230000092

Chalet in The Blue Mountains

4.93 out of 5 average rating, 326 reviews

Immaculate Blue Mountains chalet

Welcome to our cozy chalet located in walking distance of Blue Mountain village. The chalet has been recently updated, including a luxurious king bed. Through winter, enjoy a relaxing evening by the fire, after a day on the slopes. In summer, enjoy time at the pool, after day on the golf course. The chalet is equipped with everything you need for a tranquil getaway. Enjoy free shuttle service to the village. STA Licence # LCSTR20220000127

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

Kick off your hiking boots at these rustic lodgings

Chalets

Adventure-ready homes with après-ski style

Houses

A space thats all yours, with room for everyone

Popular amenities for Grey County rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Nottawa

4.94 out of 5 average rating, 17 reviews

Nature Retreat in The Pretty River Valley for 6

Home in The Blue Mountains

4.87 out of 5 average rating, 31 reviews

Spacious Chalet close to Ski resort. Pet friendly!

Home in The Blue Mountains

4.83 out of 5 average rating, 94 reviews

Cozy & Private Townhouse - Walk to Village!

Home in The Blue Mountains

4.89 out of 5 average rating, 194 reviews

Large 4 Br - 4.5 Bath; Sauna/Shuttle Bus/2 King bd

Home in Chatsworth

4.82 out of 5 average rating, 11 reviews

Charming Country Home with Pool & Hot tub

Home in The Blue Mountains

4.85 out of 5 average rating, 94 reviews

Spacious 4BR Snowbridge Home with Shuttle Access

Home in Meaford

4.97 out of 5 average rating, 72 reviews

Plume- Guest house

Home in The Blue Mountains

4.95 out of 5 average rating, 167 reviews

Serene mountainside home View/Shuttle Bus/Pool

Condo rentals with a pool

Condo in The Blue Mountains

4.85 out of 5 average rating, 99 reviews

Blue Mountain Getaway at North Creek Resort

Condo in The Blue Mountains

4.79 out of 5 average rating, 170 reviews

Mountainside Escape - Ski in / Ski out

Condo in The Blue Mountains

4.92 out of 5 average rating, 467 reviews

*Blue Mountain Village* Walk To Blue, Pool, HotTub

Condo in The Blue Mountains

4.89 out of 5 average rating, 151 reviews

Close to Village, 2 Bedrooms , Rivergrass

Condo in The Blue Mountains

4.8 out of 5 average rating, 192 reviews

Blue Mountain Escape, WIFI, Base of North lift

Condo in The Blue Mountains

4.92 out of 5 average rating, 137 reviews

Large Luxury Condo +full crib - steps to village

Condo in The Blue Mountains

4.86 out of 5 average rating, 166 reviews

Still Winds - Shuttle to Ski hills and Village

Condo in The Blue Mountains

4.94 out of 5 average rating, 240 reviews

Cozy & Charming Retreat at Blue Mountain

Destinations to explore