Holiday houses in Cockpit Island

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Top-rated holiday rentals in Cockpit Island

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Guest favourite
An open-concept living area features a cozy sectional sofa and a coffee table. A wall-mounted TV is positioned above a contemporary fireplace. Natural light is welcomed through sliding glass doors that lead to a private outdoor space, offering a sense of comfort and relaxation.
Apartment in Hamilton
4.86 out of 5 average rating, 132 reviews

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.

Guest favourite
Dome in Burlington
4.96 out of 5 average rating, 233 reviews

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!

Top Guest favourite
A vibrant artwork of a colorful frog is displayed on the wall, contrasting with the neutral tones of the room. A green plant adds a touch of nature, while a cozy futon is positioned against the wall, contributing to a welcoming ambiance.
Guest suite in Hamilton
4.86 out of 5 average rating, 191 reviews

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

Guest favourite
The airy bedroom features a spacious bed with a light blue blanket and soft grey pillows. A ceiling fan provides airflow, while artwork adorns the wall. A small seating area and dresser are visible, with a doorway leading to another room in the background.
Home in Hamilton
4.86 out of 5 average rating, 212 reviews

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

Superhost
The spacious living area features cathedral ceilings with exposed wooden beams. Comfortable seating is arranged around a round coffee table, with a modern television and entertainment unit positioned against the wall. Natural light floods in through multiple windows, enhancing the open layout.
Home in Hamilton
4.82 out of 5 average rating, 128 reviews

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!

Guest favourite
Two elegant wine glasses are positioned beside a small vase filled with white flowers. A decorative art piece featuring a wine bottle, glass, and cheese rests on the wall above, contributing to a refined ambiance.
Apartment in Hamilton
4.87 out of 5 average rating, 105 reviews

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.

Top Guest favourite
Guesthouse in Hamilton
5 out of 5 average rating, 171 reviews

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.

Superhost
A modern living area is showcased with large windows, allowing natural light to fill the space. A colorful yellow sofa and blue chairs provide seating. An entertainment unit features a television against a vibrant mural of cacti. Wooden flooring adds warmth to the contemporary design.
Hotel room in Hamilton
4.78 out of 5 average rating, 367 reviews

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.

Top Guest favourite
Loft in Hamilton
4.98 out of 5 average rating, 165 reviews

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.

Top Guest favourite
A spacious bedroom features a combination of pink walls and exposed brick, enhancing the vibrant atmosphere. The area includes a large bed dressed in white sheets, a black wardrobe, and a vanity with lights. Natural light fills the room through a prominent window, creating an inviting space.
Home in Hamilton
4.92 out of 5 average rating, 148 reviews

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.

Superhost
The hillside villa features multiple levels with large windows offering expansive views. Smooth wooden decks are visible, surrounded by greenery, while a staircase leads to the entry. Reflective glass accents enhance the modern design, blending harmoniously with the natural surroundings.
Villa in Burlington
4.94 out of 5 average rating, 171 reviews

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.

Top Guest favourite
A spacious living area features hardwood flooring and a ceiling fan. An entertainment unit with a television is centered against a white wall, coupled with a decorative fireplace. A comfortable gray sofa is positioned to the left, with a small dining table adorned with sunflowers on the right.
Home in Hamilton
4.96 out of 5 average rating, 158 reviews

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

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  2. Canada
  3. Ontario
  4. Hamilton
  5. Cockpit Island