Holiday rentals with a pool in Grey County

4.89 out of 5 average rating, 152 reviews

Home in Chatsworth

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)

4.98 out of 5 average rating, 235 reviews

Home in Owen Sound

The Butchart Estate: your perfect family retreat!

Give them a holiday to remember. With fresh air & freshwater beaches. Escarpment views, grottos & waterfalls. It's a great time to get yourself a little more Canada in beautiful Grey-Bruce. Settle in to our beautiful and well-equipped heritage home. Enjoy the gourmet kitchen, relax in your private indoor pool & hot tub, curl up by the fireplace, play board games galore. Outdoors, we're famous for our hills, forests, lakes and rivers. But don't miss the music, museums, and amazing foodie scene.

4.96 out of 5 average rating, 170 reviews

Home in Meaford

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 2 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 April to Nov. 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.

4.86 out of 5 average rating, 370 reviews

Tiny home in Meaford

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/pool opens end of May or June.

4.87 out of 5 average rating, 246 reviews

Northern Peaks - Outdoor Pool / Shuttle to Blue

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.

Townhouse in The Blue Mountains

4.96 out of 5 average rating, 208 reviews

Après Blue- 2bed2bath w/Pool 6 min walk to village

Welcome to Apres Blue at Blue Mountain! Unbeatable location @ 110 Fairway Court, only a 5 minute walk to Blue Mountain Village, Ski lifts & Monterra Golf Course. Professionally decorated ground floor unit with full kitchen, gas fireplace, high speed internet, walk out private patio with outdoor dining area, private gas BBQ and shared seasonal pool. This spacious ground floor, 2 bedroom, 2 full bathroom end unit townhouse has everything you need to enjoy your stay! License #LCSTR20230000084

4.94 out of 5 average rating, 110 reviews

Cottage in Meaford

Woodski Retreat w/Heated Pool on 3+ Private Acres

This private mountain retreat is just 15 minutes from Blue Mountain, features 3.2 acres of beautiful scenery, a swimming pool and a renovated home for 10 guests (Max 8 adults). The house sits at the foot of a private 500ft mountain that is yours to explore all year around. Inside, there is a spacious home built for entertainment. Enjoy all-year fun at the property or head out to enjoy the amazing activities nearby. Only 5 minutes to the beach and 15 minutes to the best skiing in Ontario!

Flat in The Blue Mountains

4.99 out of 5 average rating, 146 reviews

Evergreen Studio-KingBed/Pool/HotTub/Shuttle

Renovated studio unit at the North Creek Resort featuring: * King Bed * SMART TV, High-Speed Rogers Ignite WIFI and TV * New Pull Out Sofa * Stone Fireplace * Modern, Stylish Decor *please note there is not a traditional oven- there is a microwave/convectional oven combo along with a stove top *Shuttle Service *2 Year Round Hot Tubs *Seasonal Pool (open as of May 31st 2025) *Tennis Courts *Ski or Hike In/Out to the North Hill (hiking trails, intermediate-advanced daytime skiing)

4.98 out of 5 average rating, 166 reviews

Lovely 3 Bedroom Condo with Stunning View and Pool

Beautifully Newly Renovated Condo Located in Rivergrass on Fairway Crt, which is in the heart of Blue Mountain and Steps to the Village! Condo features 3 bedrooms(One king, two Queen and Two Twin beds with trundle pullouts), 2 full baths, kitchen, washer/dryer, living room, and dining room. Outdoor Pool (Open from June 1 to Sept) and Hot Tub(All Year). Short walk or take the shuttle bus to the village. Our cleaners are extensively disinfecting and sanitizing between each booking.

4.93 out of 5 average rating, 302 reviews

Cozy Studio Mountainside stay in Blue Mountains

Enjoy the beauty of Spring in Blue Mountains. 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.Two hot tubs are open daily. Access to the North side of Blue from our condo. The Blue Village is only a 5 minute drive away with great local restaurants and shops.

Superhost

4.84 out of 5 average rating, 405 reviews

Ski in/out @ North Creek W King bed! New Hot Tub

Welcome to our beautiful studio at the foot of Blue Mountain ski hills. Fully renovated from top to bottom in 2021 and ready for visitors! 'Cascade Cabin' is a modern studio which sleeps 3 and features a King bed with a queen sofa bed in the living area. Unit features a fully equipped kitchen with seating for 3, full bathroom with shower & new soaker tub. The condo is located within minutes from Blue Mountain Village and within walking distance to the north ski lift.