Vacation rentals near The Point Gallery
We found 560 vacation rentals — enter your dates for availability
Choose the perfect vacation home within easy reach of The Point Gallery. Vacation homes provide the best amenities for your stay with friends, family, or just your pet, such as WiFi and a fireplace. At the end of the day, you'll find a rental to meet everyone's needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - The Point Gallery
Showing deals for:Nov 21 - Nov 28
Image gallery for Luxurious Lake front Island Twnhome Friday Harbour
8.88.8 out of 10 rating
Excellent
(9 reviews)
Luxurious Lake front Island Twnhome Friday Harbour
Innisfil, ON
10% off
Price is CA $294
CA $294
CA $2,834 total
CA $2,834 total
includes taxes & fees
Image gallery for Luxury Lake Simcoe Waterfront Cottage
1010 out of 10 rating
Exceptional
(5 reviews)
Luxury Lake Simcoe Waterfront Cottage
Innisfil, ON
15% off
Price is CA $1,639
CA $1,639
CA $14,925 total
CA $14,925 total
includes taxes & fees
Image gallery for Waterfront Luxury with Pool
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Waterfront Luxury with Pool
Innisfil, ON
15% off
Price is CA $1,821
CA $1,821
CA $16,071 total
CA $16,071 total
includes taxes & fees
Image gallery for Friday Harbour Prime Location - Luxurious Lakeside Escape
1010 out of 10 rating
Exceptional
(5 reviews)
Friday Harbour Prime Location - Luxurious Lakeside Escape
Innisfil, ON
25% off
Price is CA $225
CA $225
CA $2,296 total
CA $2,296 total
includes taxes & fees
Image gallery for 4 Acre Estate | 7 Bedrooms | Sleeps 20 | 5min to Downtown
9.89.8 out of 10 rating
Exceptional
(9 reviews)
4 Acre Estate | 7 Bedrooms | Sleeps 20 | 5min to Downtown
Barrie, ON
10% off
Price is CA $976
CA $976
CA $8,989 total
CA $8,989 total
includes taxes & fees
Image gallery for Comfy Waterfront Cottage - 10 min from Casino Rama
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Comfy Waterfront Cottage - 10 min from Casino Rama
Ramara, ON
10% off
Price is CA $351
CA $351
CA $3,426 total
CA $3,426 total
includes taxes & fees
Image gallery for Barrie Kempenfelt Bay Waterfront Cottage(Muskoka by the City)
9.09.0 out of 10 rating
Wonderful
(16 reviews)
Barrie Kempenfelt Bay Waterfront Cottage(Muskoka by the City)
Shanty Bay, ON
15% off
Price is CA $438
CA $438
CA $4,036 total
CA $4,036 total
includes taxes & fees
Image gallery for Shallow Beach Lakefront Cottage perfect with Kayak, Firepit, BBQ + Playground
9.49.4 out of 10 rating
Exceptional
(8 reviews)
Shallow Beach Lakefront Cottage perfect with Kayak, Firepit, BBQ + Playground
Innisfil, ON
10% off
Price is CA $759
CA $759
CA $7,094 total
CA $7,094 total
includes taxes & fees
Image gallery for Unplug at the Point: relax and recharge at your own private lakefront paradise
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Unplug at the Point: relax and recharge at your own private lakefront paradise
Georgina, ON
10% off
Price is CA $437
CA $437
CA $3,934 total
CA $3,934 total
includes taxes & fees
Image gallery for Stunning Waterfront Luxurious Lakehouse .Great For Family Stays!
1010 out of 10 rating
Exceptional
(15 reviews)
Stunning Waterfront Luxurious Lakehouse .Great For Family Stays!
Innisfil, ON
10% off
Price is CA $900
CA $900
CA $8,268 total
CA $8,268 total
includes taxes & fees
Image gallery for CHARMING CUSTOM HOME BESIDE PARK,WALK TO BEACH
9.89.8 out of 10 rating
Exceptional
(23 reviews)
CHARMING CUSTOM HOME BESIDE PARK,WALK TO BEACH
Barrie, ON
5% off
Price is CA $166
CA $166
CA $1,569 total
CA $1,569 total
includes taxes & fees
Image gallery for Cozy house at south end Barrie
1010 out of 10 rating
Exceptional
(7 reviews)
Cozy house at south end Barrie
Barrie, ON
10% off
Price is CA $146
CA $146
CA $1,462 total
CA $1,462 total
includes taxes & fees
Image gallery for Luxury Guest House With Private Hot Tub and Trails
1010 out of 10 rating
Exceptional
(8 reviews)
Luxury Guest House With Private Hot Tub and Trails
Oro-Medonte, ON
10% off
Price is CA $190
CA $190
CA $1,950 total
CA $1,950 total
includes taxes & fees
Image gallery for Lakeview 3-Story Family Cottage | 4BR Retreat in Georgina
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Lakeview 3-Story Family Cottage | 4BR Retreat in Georgina
Jacksons Point, ON
20% off
Price is CA $192
CA $192
CA $1,914 total
CA $1,914 total
includes taxes & fees
Image gallery for Sunrise Villa on the Lake
9.09.0 out of 10 rating
Wonderful
(10 reviews)
Sunrise Villa on the Lake
Innisfil, ON
10% off
Price is CA $449
CA $449
CA $4,194 total
CA $4,194 total
includes taxes & fees
Image gallery for Lake Simcoe Waterfront Cottage Getaway
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Lake Simcoe Waterfront Cottage Getaway
Ramara, ON
22% off
Price is CA $468
CA $468
CA $4,274 total
CA $4,274 total
includes taxes & fees
Image gallery for Rustic luxury chalet with pool, a two-minute walk to beach, park and playground!
1010 out of 10 rating
Exceptional
(12 reviews)
Rustic luxury chalet with pool, a two-minute walk to beach, park and playground!
Barrie, ON
10% off
Price is CA $228
CA $228
CA $2,041 total
CA $2,041 total
includes taxes & fees
Image gallery for Lake Simcoe - Bayview Beach Lakefront cottage 1 hour North of Toronto
9.89.8 out of 10 rating
Exceptional
(25 reviews)
Lake Simcoe - Bayview Beach Lakefront cottage 1 hour North of Toronto
Innisfil, ON
10% off
Price is CA $318
CA $318
CA $2,983 total
CA $2,983 total
includes taxes & fees
Image gallery for Simcoe Waterfront Home with new Hot Tub ( near Casino Rama)
1010 out of 10 rating
Exceptional
(8 reviews)
Simcoe Waterfront Home with new Hot Tub ( near Casino Rama)
Orillia, ON
10% off
Price is CA $450
CA $450
CA $4,147 total
CA $4,147 total
includes taxes & fees
Image gallery for Family-Friendly Cottage on Lake Simcoe with Private Shared Beach Access
9.69.6 out of 10 rating
Exceptional
(69 reviews)
Family-Friendly Cottage on Lake Simcoe with Private Shared Beach Access
Georgina, ON
5% off
Price is CA $167
CA $167
CA $1,609 total
CA $1,609 total
includes taxes & fees
Image gallery for Barrie house close to all amenities
9.09.0 out of 10 rating
Wonderful
(24 reviews)
Barrie house close to all amenities
Barrie, ON
10% off
Price is CA $137
CA $137
CA $1,407 total
CA $1,407 total
includes taxes & fees
Image gallery for Retreat to heaven on earth. An unforgettable luxury estate in paradise
8.68.6 out of 10 rating
Excellent
(11 reviews)
Retreat to heaven on earth. An unforgettable luxury estate in paradise
Springwater, ON
15% off
Price is CA $338
CA $338
CA $2,998 total
CA $2,998 total
includes taxes & fees
Image gallery for Detached private bungalow, sleeps10, 4min to lake/downtown, NO STAIRS/10 carpark
9.69.6 out of 10 rating
Exceptional
(19 reviews)
Detached private bungalow, sleeps10, 4min to lake/downtown, NO STAIRS/10 carpark
Barrie, ON
10% off
Price is CA $199
CA $199
CA $1,854 total
CA $1,854 total
includes taxes & fees
Image gallery for Horseshoe Valley Fieldview Farm
9.89.8 out of 10 rating
Exceptional
(41 reviews)
Horseshoe Valley Fieldview Farm
Oro-Medonte, ON
10% off
Price is CA $315
CA $315
CA $2,884 total
CA $2,884 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - The Point Gallery
Lakefront Cottage w/Hot Tub, BBQ Grill, Patio, Fire Pit, Dock, Sauna, Fire Place
Sleeps 13 · 5 bedrooms · 2+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
17 reviews(17 reviews)
Amazing fully upgraded 3 bedroom+ new furniture, 1 full bath lake property
Sleeps 8 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Sandy Beach Cottage steps to Lake Simcoe - 1 hr 20 mins from Toronto
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Romantic Log Cabin in the Woods - Hot Tub under the Stars -80 km's from CN Tower
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
119 reviews(119 reviews)
Two Story Boathouse Located On East Side of Lake Simcoe
Sleeps 4 · 2 bedrooms · 0+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
28 reviews(28 reviews)
Swing Bridge Cottage on Lake Simcoe - Waterfront
Sleeps 8 · 4 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Top rated rentals - The Point Gallery
Great getaway
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
I stayed here with my husband and in-laws - what a fantastic place. Enough space for everyone to either hang out together or have their own space. The barn was such a great place to hang out too. All in all, a great time. Would stay again!
Justine K.
Stayed Jul 2025
Great communication and excellent cleanliness
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
My friend and I had a very comfortable stay at this location. Excellent cleanliness and Jesse was extremely helpful, available, and good to communicate with. Nice to have a fridge, coffee maker, kettle, toaster oven and portable stove element to make a quick breakfast with. Very comfortable bed. Overall a great stay. Thank you Jesse!
Alicia C.
Stayed Jul 2025
Great spot
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
My husband,13 year old son and I stayed here for 3 nights and had a wonderful time. Clean, and with easy check-in and check-out. We loved the porch!
Shannon C.
Stayed Jun 2025
Exceptional Stay
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
We thoroughly enjoyed our stay! The guest home was wonderful. It was charming, comfortable, clean and perfectly located. Kara was extremely helpful, kind and professional!
Elizabeth K.
Stayed Jun 2025
Peaceful weekend with friends
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
This location provided for a dream vacation away from reality. There are actually 4 bedrooms instead of just the 2 that are listed. The kitchen was well stocked with essentials and had more than enough dishes, glasses, pots and pans. The macrame chairs overlooking the water are perfect for relaxing and the beds are all comfortable. We enjoyed the board games and puzzles as well. Would definitely book again!
Christine H.
Stayed May 2025
Excellent rental
1010 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Spotlessly clean and nicely set out. Hot tub was heaven! Very close to absolutely everything. Neighbourhood is quiet as a mouse. Highly recommend this rental. Not good for those with a mobility issue. Great communication with the owner.
Jacqueline B.
Stayed Mar 2025
Great place.
1010 out of 10
Exceptionalexceptional
8 reviews(8 reviews)
Thanks to the host!! Your place was perfect and had many amenities included. A cozy home away from home for our family. Thanks again.
Alain B.
Stayed Jan 2025
Great spot!
1010 out of 10
Exceptionalexceptional
2 reviews(2 reviews)
Mr B’s place was great. Conveniently located, great price, clean with ample room. The house was equipped with everything you needed. Across the street is a fire pit and the lake. We snowmobile/fish so being lakeside was perfect for us. Mr B was prompt in getting back to us with any questions and was very kind and understanding. Would definitely stay here again.
Sarah B.
Stayed Jan 2025
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value