Holiday houses in Cockpit Island

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.

Value · Family · View

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!

Family · Location · Indoor spaces

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

Value · Location · Quiet

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.

Family · Location · Decor

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.

Location · Value · Parks

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.

Value · Family · Condition

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.

Value · Location · Parking

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.

Family · Value · Hot tub

Private Top-Floor Loft • Prime Hamilton Location

Bright, private top-floor suite in central Hamilton, just steps from Locke St and 2 blocks to the TD Coliseum. Walk to cafés, restaurants, and events at Bridgeworks, or explore nearby breweries, trails, and waterfalls. Only 3.5 km to McMaster University, 45 mins to Toronto, and 1 hr to Niagara Falls. Includes dedicated on-site parking. Hosted by an experienced Superhost offering a comfortable, reliable stay for both business and leisure travellers.

Value · Location · Sleep quality

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.

Location · Family · Kitchen

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!

Family · Value · Sleep quality

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 Parking info is under DIRECTIONS

Location · Value · Hospitality