
Holiday houses in Cockpit Island
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Top-rated holiday rentals in Cockpit Island
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Frenchman’s Pass - Cozy nook on the Hamilton brow
Welcome to your home away from home! This charming suite at the back of our home has a separate entrance and a convenient private deck. Nestled on the Hamilton Mountain in one of Hamilton's most upscale neighborhoods, we are steps from the scenic brow offering the perfect blend of tranquility and convenience. High-speed Wi-Fi, smart TV, private, on-site parking and essentials for a relaxing stay. Situated centrally, you're just minutes from hospitals, shopping, restaurants, and public transit.

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!

Super Cute Basement Apartment
This is the best location for your Hamilton Stay. This Basement Apartment is walking distance to great cafes, food, and entertainment. It's a really cozy space & is perfect for crashing after a busy day! Benefits: - Close to Public Transportation - Close to the best of Hamilton - Easy access to Toronto & Niagara - We take pride in hosting & want your stay to be as good as it can be - Nature Features: - Separate Entrance & Self-Checkin - Double Bed - Futon for sleeping 1-2 more - Free Parking

Private Oasis on our 3rd floor
Our THIRD floor apartment is quiet and private. Front door has a code lock, it is important that you hold the DOOR HANDLE towards you as you do the CODE. Your space has a code lock. This space does not have a private entrance, you enter the front door up the stairs, the white door on your left is yours. The space is quite airy and relaxing, kick your shoes off and relax. Continental BREAKFAST must be requested when you book or checkin. $8.00 a day Parking info is under DIRECTIONS

Trendy Downtown Home + Parking, COZY Hess House!!!
Circa 1920, fully renovated beautiful 1 fl, 2 Bdrm + 1 bath home with front parking for 2 cars, private backyard is centrally located in the downtown core & Ent District. Walk score of 94 & a transit score of 83, within walking distance to everything, all Hospitals, Juravinski, Hamilton General Hospital, within 4 km's of McMaster University & McMaster Hospital, Bay Front Park, West Harbour Go Station all other amenities. This cozy home sleeps 6 & will having you yearning for another visit!

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.

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.

Sunny and Private Kirkendall South Loft Apartment
Location! Location! Location! Find your home away from home steps from the Chedoke stairs and golf course, the Bruce Trail, Locke Street restaurants, three major hospitals, McMasters University, Mohawk College, public transport and easy highway access! This warm and inviting sunny loft apartment will meet all your needs. It is the perfect location for golfers, hikers, cyclists, foodies, and people just seeking tranquility and peace. Street parking is free, legal and easy to find.

Chic Oasis | Luxury 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.

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.

Harbour front CHA CHA CHA - Lake view house
Live by the water! Relax with your family at this peaceful 2Bd 1Bath Lakeview property in Hamilton West Harbour. Enjoy a cup of Nespresso on the house. Steps from the Bayfront park with beautiful lake views, Collective Arts Brewing to enjoy a cold local beer, trendy James St N for all the restaurants, West Harbour Go Train Station , and much more! It is located within an hour from Toronto and Niagara Falls. Book your stay now!
Popular amenities for Cockpit Island holiday rentals
Other great holiday rentals in Cockpit Island

Trouvaille - something wonderful

Executive Suite close to Mac

Albany Apartment- Private basement suite

The Coop at Mountain Ridge

The Bayfront - Harbour Views + Private Pool!

Charming retreat with lake view

Stay in Central James South with Parking and WIFI

Separate Entrance|Entire, Cozy Suite|Self check-in
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Mississauga Holiday rentals
- Pocono Mountains Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Pittsburgh Holiday rentals
- Niagara Falls Holiday rentals
- Erie Canal Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Rogers Centre
- CN Tower
- Scotiabank Arena
- Union Station
- University of Toronto
- Enercare Centre
- Metro Toronto Convention Centre
- BMO Field
- The Danforth Music Hall
- Harbourfront Centre
- Distillery District
- Nike Square One Shopping Centre
- Toronto Eaton Centre
- Exhibition Place
- Trinity Bellwoods Park
- Niagara Falls State Park
- Downsview Park
- Financial District
- Wilfrid Laurier University
- Massey Hall
- Casa Loma
- Dufferin Grove Park
- York University
- Casino Niagara




