Jayne's Cottages


Cottage in Rosseau

  • 5 Beds
  • 3.0 Baths
  • 10 Guests
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Cottage in Rosseau

  • 5 Beds
  • 3.0 Baths
  • 10 Guests
Winchester - property


Cottage in Rosseau

  • 5 Beds
  • 3.0 Baths
  • 10 Guests


Cottage in Rosseau

Booking direct with us guarantees the lowest price. Select dates to calculate taxes and fees. Inquire for off-season and special pricing.

Stay Information

  • Summer WeekFromJun 14-July 19 & Aug 11-Sep 9C$22,500 /Summer Week
  • Super Peak WeekFromJul 19-Aug 11 C$24,210 /Super Peak Week
  • Off Season WeekendFromOct 9-Dec 22 & Jan 3-May 17 C$3,900 /Off Season Weekend
  • Holiday WeekFromDec 20-Jan 3 C$8,000 /Holiday Week

Property Details

4 bedroom + bunkie, 3 bathroom cottage with full walkout and direct access to the boathouse w/ rooftop patio, outdoor kitchen and dream entertainment space while capturing panoramic waterfront views all within minutes of the Village of Rosseau!

Located off Pennisula Road in the peaceful northern Muskoka area. Less than 10 minutes to the Town of Rosseau with many options for groceries and dining including the Rosseau Farmers Market every Friday during the summer! 15 minutes to Minett's JW Marriott. Just 30 minutes to Port Carling, the Muskoka central hub with access to the other Muskoka lakes.

WINCHESTER sits slightly elevated above the Lake Rosseau shoreline, with four levels of decking bringing ample outdoor seating throughout. Off the main floor of the cottage is the large cottage deck with quick access to the bunkie or a few stairs that will take you to the impressive boathouse rooftop patio where there is a covered and uncovered portion, right above the water. Under the covered portion is an outdoor kitchen with a barbecue, a bar area, a propane fire pit, as well as an outdoor dining table with seating for 8 and a high table with seating for 4. The uncovered portion at the end of the deck has an outdoor sectional and coffee table, with exceptional views and excellent sun. From the cottage deck, you can continue all the way down to the water level where there are three different docks to choose from, depending on what kind of sun exposure you'd prefer throughout the day. On the far side of the boathouse is a stretch of docking with two lounge chairs, directly in front of the cottage is the largest dock with 6 lounge chairs with an umbrella, and the last dock has four Muskoka Chairs plus two jet ski lifts. Between the shoreline and the cottage are beautiful gardens and landscaping making it a gorgeous little adventure walking amongst the property. Also on the property are two fire pits, one with seating for 10!

Great room with 2 sectional couches with chaises, wood-burning fireplace, and large TV
Spacious kitchen with large fridge/freezer, wine rack, and island seating for 4
Dining table for 8 with walkout to deck and Muskoka Room
Screened-in Muskoka Room with a couch and 4 sofa chairs and walkout to deck
Games room complete with a pool table, ping pong table, air hockey table, foosball table, and a classic arcade with 3,100 original arcade games
Separate sitting area with a couch
Three-piece bathroom, bed chair, small kitchenette.

Bathroom 1 - Powder Room
Bedroom 1 - King(primary) with ensuite, walkout to private deck, and TV
Bathroom 2 - 3-Piece primary ensuite with stand-alone shower
Bedroom 2 - Queen
Bedroom 3 - Queen
Bedroom 4 - 2 Doubles
Bathroom 3 - 4-piece bath with stand-alone shower

Bedroom 5 - Queen

All-day sun
Stocked Games Room
Multiple outdoor sitting areas
Wood-burning fireplace
Classic Arcade with 3,100 original arcade games
2021 Updates: Updated firepit area and Sauna
1 interior boat slip

2 Firepits
2 Kayaks
Water Trampoline

This cottage is equipped with satellite, wifi, air conditioning and an automatic generator
This bunkie is not equipped with air conditioning
This cottage participates in Jayne's White Linen Program
This cottage includes 10 hours of midweek housekeeping during peak season rentals

Boathouses, Bunkies and 3 Season Muskoka Rooms not habitable from Thanksgiving-Victoria Day Weekend
Outdoor furniture is not out from Thanksgiving-Victoria Day Weekend
Water toys are not available Thanksgiving-Victoria Day due to safety concerns

5 cars

Maximum 10 guests
Non-smoking cottage
Pets considered

Check-in time 4:00 pm
Check-out time 10:00 am




Sleeping Arrangements

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

2 Double Beds

Bedroom 5

1 Queen Bed



36 Winchester Drive
Rosseau, Ontario


Cancellation Policy

Cancellation Policy by Agency -
If the Cottage Property is for any reason not rentable prior to commencement of the Rental Period then the Guest Agreement will be null and void and all Advance Deposits will be refunded to the Guest’s credit card within 7 days of cancellation. No additional refund or damages will be paid to the Guest or Guests.

Cancellation Policy by Guest -
Guest may cancel the agreement before150 days prior to the start of the rental period, the deposit will be returned less a fee of $2000 per week of reservation if rental is under $20,000 per week. For rentals at $20,000 and over, the cancellation fee is $4000/week of rental. If the Guest cancels the agreement 61 to 149 days prior to the start of the rental all deposits will be forfeited. If the Guest cancels the agreement less than 60 days before the start of the rental agreement the Guest is responsible for the full amount of the rent and is not entitled to any refund.

Cancellation Policy on Concierge Services - Full refund on deposits made 31 days or more prior to arrival. For cancellation of concierge service for arrivals less than 31 days away, all deposits will be forfeited.

Deposit Policy

Deposit Policy - 50% of Rental Amount is due at time of booking.  If your rental's arrival date is greater than 6 months, the 25% is due upon booking and 25% is due 6 months prior to the commencement of the rental.  Balance of payment is due 60 days prior to arrival. Please note that there is a $250 penalty associated with late payment of the balance between 59-46 days prior to the commencement of the rental that will be charged to your credit card. At 45 days prior to the rental, Jayne's Cottages is entitled to treat the booking as cancelled as per below.

Jayne's Cottages is entitled to treat the booking of any Guest as cancelled in the event that: a) the Guest gives written notification of cancellation; b) the Guest fails to pay the full deposit due or the balance of rent by the time specified above. In the event that the booking is so cancelled, Jayne's Cottages may re-book the property for the period concerned or for part of that period.

Bookings made within 24 hours of arrival will be charged an additional $1000 Booking Fee.
Bookings made within 48 hours of arrival will be charged a $500 Booking Fee.


Rate varies due to seasonality and holidays.

Please select your dates on our online booking calendar and use the booking engine for an exact quote. Additional Fees may include, but are not limited to, Turnover Clean, Taxes, Security Deposit and other Optional Services to enhance your stay. 

2 Guest Reviews

5 star


4 star


3 star


2 star


1 star



by Rob


Fantastic experience. Jayne greeted us, and I really appreciated the preparation that went into our stay. The place was clean and tidy, and all details looked like they were reviewed prior to our stay. The extra quality assurance that Jayne's adds is noticeable and a value-add compared to a simple transaction of a rental/airbnb. Thank you!

""thanks to the owner for making the cottage available to us!""

by Harry


Thank you for your assistance with our rental of the Winchester cottage, and please convey our sincere thanks to the owner for making the cottage available to us! The cottage offered completely unobstructed 180 degree views of the lake, the cottage rooms were both practical and beautifully furnished and there was a seemingly unlimited amount of dishes, cutlery and cooking/serving utensils to make feeding a large group easy, both in the kitchen and on the upper deck of the boathouse. In spite of some early inclement weather, the younger members of our family made very good use of the water equipment and lower level games room during the week.




Living Area & Fireplace

Great Room & Fireplace

Great Room & Fireplace

Kitchen & Bar Seating


Muskoka Room

Primary Bedroom - Upper Level

Games & Entertainment Room - Lower Level

Pool/Ping Pong Table

Pool/Ping Pong Table

Bedroom 2 - Lower Level

Bedroom 3 - Lower Level

Bedroom 4 - Lower Level

Sauna Interior

Lakeside Bunkie

Bunkie Interior

Bunkie Interior

Master Walkout

Stairway to Boathouse Deck

Covered Boathouse Deck

Covered Boathouse Deck

Uncovered Portion of Boathouse Deck

Uncovered Portion of Boathouse Deck




Aerial Views