
Holiday houses in Cockpit Island
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Top-rated holiday rentals in Cockpit Island
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Jungle Dome on a Farm! Animal Lovers Dream!
Jungle Dome Farm Stay in Burlington! Be completely immersed in farm life and all that it entails while staying in our 500 square foot geodesic dome “glamping” greenhouse dwelling! Complete with a fish and turtle pond and filled to the brim with tropical plants! Designed as a tropical vacation getaway when you can’t get away to the tropics! Situated on a 5 acre animal farm where guests can experience farm life with goats, horses, highland cows, sheep, pigs and poultry. An Animal Lovers Dream!

Cottage On Lake Ontario Niagara
OPEN TIMESLOTS AUGUST 17-23 (6 nights/7 days) AUGUST 25-29 (4 nights/5 days) Please mark this listing as a favourite to get notifications of last minute deals. Unwind at our cozy guest house. Beautiful 2-bedroom cottage. Enjoy the direct waterfront views from the living room, bedroom and wrap around composite deck. Outdoor fire pit and BBQ. Set in vineyards, peach, nectarine and plums. Close to wineries & shops. Free Tesla charging. Views from the cottage include orchards & direct Lakefront.

Trendy Downtown Home + Parking, COZY Hess House!!!
Circa 1920, fully renovated beautiful 1 fl, 2 Bdrm + 1 bath home with parking for 2 cars, private backyard is centrally located in the downtown core & Ent District. Located directly across from a 24-HR Grocery/Variety store & right next to an authentic mexican restaurant in a building I own as well. Walk score of 94 & a transit score of 83, walking distance to everything, all Hospitals, within 4 km's of Mac University & Hospital, Bay Front Park, West Harbour Go Station all other amenities.

Escarpment Dwelling!
Welcome to beautiful nature! Country road stay and enjoy farm land surrounding. Located 10 min to Dundas/ Waterdown, McMaster University. Perfect location 5 min from Rock Chapel Sanctuary, Dundas Peak. Tews Waterfalls ,Websters Falls. 2 min from Wedding venue at Dyment's Glen Drummond Farm, shop dine and fall in love with nature. Winter activities Carriage rides going back in time in the beautiful downtown Dundas. Museums and Cactus festival. West Avenue cider house drive down country roads.

Central Westdale steps from McMaster
Private Retreat Steps from McMaster self-contained basement apartment with restaurants, bars, local movie theatre, and McMaster University steps away. We're a family living upstairs you may occasionally hear little footsteps and giggles! What's included: Double be, sofa bed, Microwave, mini fridge, and Laundry room with large sink for dishes and washing up WiFi, parking, and fresh linens note: No full kitchen, and a few areas have lower ceilings (5'7") near the entrance and sleeping area.

Boutique coach house with Scandinavian Steam Sauna
Morwick Lane - a boutique retreat steps from Hamilton’s best downtown spots, and just an hour from Toronto and Niagara Falls. This restored coach house features curated comforts including a sleek fireplace, luxurious bedding, and a cedar Scandinavian sauna. Enjoy the garden shower after your steam sauna, then unwind in the courtyard with a fireplace and stunning gardens. Perfect for a romantic escape or solo wellness retreat, Morwick Lane invites you to experience something unforgettable.

Fully-Furnished Boutique 1 Bedroom Suites
The Laundry Rooms is situated on one of our favourite streets in Hamilton. Featuring cozy pubs, local coffee shops, and a 10-minute walk from the downtown core, Augusta Street has a small-town vibe in the heart of the city. Live like a local with all the comforts and amenities of home in our contemporary suites designed for the professional traveller. Pets are welcome and we can't wait to meet your dog (a deep cleaning fee applies (except for assistance animals))... and you, of course.

Chic Oasis | Stay in the Heart of Hamilton
Step into a stunning modern-retro escape where bold red tones, playful pink accents, and vintage exposed red bricks create an unforgettable vibe. Perfectly located just steps from vibrant Hess Village, you're within walking distance to concerts, sports venues, art galleries, boutiques, and top-tier dining. Explore trendy Locke Street or hike the Escarpment nearby. With cozy bedrooms, chic outdoor spaces, and irresistible charm, this gem is a true city retreat.

Summertime! Steam shower+breakfast+rooftop hottub
Nestled in a picturesque escarpment community overlooking the historic town of Dundas, The Hayloft is a charming getaway for anyone looking for an escape and a breath of fresh air. Relax in the steam shower inside or the hot tub on the fully private rooftop deck overlooking gardens. Take a nap on the lounge chairs. Visit with the chickens, make friends with the fish or the frogs. Unwind at night with a movie in bed, with breakfast (surcharge) in the morning.

Waterfront Hillside Villa
Welcome to your stunning Hillside Villa situated on 150' of waterfront. Enjoy the peaceful surroundings and quiet Bay views from your 3 private outdoor decks & hot tub. Entertaining is easy in this gourmet kitchen, which is open to 1 of 2 fireplaces, family room & dining room with floor to ceiling views of the Bay. Breathe taking views of the Bay from your private dock. Hidden gems: gym, 2nd kitchen, foosball table, EV charging and private trail.

Modern City Retreat on Hamilton's Best Street
Stylish 2BR/1.5BA space with high ceilings, exposed brick & designer finishes perched on James Street North - Hamilton's hottest dining, entertainment & arts district. Steps to TD Coliseum! Private entrance, ultra-fast WiFi, expansive open spaces & massive patio with urban views. Walk to galleries, craft breweries, unique bars, farmers market, excellent parks, the waterfront & top restaurants. Your stylish downtown escape awaits!

Gallery Suite
The Gallery Suite near Locke St. and McMaster is ideal for business or leisure stays. This bright, open-concept suite with a separate bedroom features unique artwork by Guelph artist Ryan Price. Located above a quiet RMT clinic, you'll enjoy a peaceful and private stay. Walking distance to trendy shops and cafes. Free parking is included for your convenience. Book now to experience a blend of comfort, art, and convenience!
Popular amenities for Cockpit Island holiday rentals
Other great holiday rentals in Cockpit Island

Cozy Guest Suite | Kitchenette & modern Bath

Charming country retreat 5 min drive to downtown

Luxury Locke Street Loft

A cozy country loft

The Steel-Modern

Chic Downtown Stay, Near Top Local Spots

Panoramic Lake Views | Hot Tub • Beach • Firepit

Blush on Sherman | Chic Basement near Gage Park
Destinations to explore
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- CN Tower
- Rogers Centre
- Scotiabank Arena
- University of Toronto
- Union Station
- Downsview Park
- Metro Toronto Convention Centre
- The Danforth Music Hall
- Niagara Falls State Park
- Harbourfront Centre
- Toronto Eaton Centre
- Scarborough Town Center
- Nike Square One Shopping Centre
- Niagara Falls
- Exhibition Place
- Elora Gorge
- Yorkdale Shopping Centre
- Casa Loma
- Trinity Bellwoods Park
- York University
- Sheppard–Yonge Station
- Massey Hall
- Coca Cola Coliseum
- Enercare Centre





