Vacation rentals in Upper North Sydney

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Top-rated vacation rentals in Upper North Sydney

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A serene seating area is positioned along the waterfront, featuring two bright blue chairs arranged around a small table. Green plants border the wooden deck, which extends to the water's edge, emphasizing a peaceful outdoor space.

Home in Bras D'or

4.95 out of 5 average rating, 127 reviews

Cozy waterfront home perfect for a couples getaway

Cozy & very clean waterfront home, perfect for a couples getaway. Property is overlooking the Saint Andrews Channel with access to a small private wharf. Unfortunately you cannot dive from or dock boat on wharf. Ideal for swimming, kayaking, paddle boarding, canoeing or simply just putting your feet up and relaxing. After a day on the water relax in front of a small campfire and watch the boats returning for the evening as the sunsets. A perfect, well deserved day of peace, calm and tranquility.

Top guest favorite

A bright kitchen is highlighted by vibrant green walls and modern cabinetry. String lights add a soft glow above the dining area, featuring a long table with minimalist metal chairs. The space is equipped with stainless steel appliances and an open layout, enhancing the connection between cooking and dining areas.

Home in Sydney Mines

4.94 out of 5 average rating, 47 reviews

Ocean Air Guesthouse

Unwind and relax at our Ocean Air Guesthouse. This bright, three bedroom home offers a full kitchen with a spacious dining area. Day trips or evening strolls on the beach are easy as we are located within walking distance of several coastal beaches, and only an 1 1/2 hour drive to the beautiful Cabot Trail. We have a dedicated workplace provided so you can make it a working vacation. Going to Newfoundland? We are only a five minute drive to the ferry! *Foam mattress for a 7th guest available

Top guest favorite

A sunlit exterior of a restored barn features warm wooden siding and multiple large windows. The wrap-around deck includes a dining table and chairs, with Adirondack seating for relaxation. The backdrop highlights a serene waterfront view, enhancing the inviting outdoor space.

Loft in Alder Point

4.99 out of 5 average rating, 84 reviews

Cape Breton’s Shoreline Point

Waterfront Apartment Nestled in a Restored Barn with Breathtaking Views. Enjoy a Maritime experience, walk along the shoreline. Catch the Sunsets. Enjoy the local cuisine. Private 2 bedroom suite in a restored barn, sleeps 6. Perched on the St. Andrew’s Channel leading to the Brasd’Or Lakes and to the Atlantic Ocean. Just steps from a working Maritime Warf that will offer you a front row seat to watch the local fishermen. Centrally located. Minutes from the Trans-Canada Highway and NFLD Ferry.

Top guest favorite

A serene grassy landscape is illuminated by soft sunlight breaking through the clouds. Colorful flowers and lush greenery frame the view, while a covered wooden structure offers shadows nearby. The ocean can be seen in the distance, enhancing the peaceful atmosphere.

Home in Sydney Mines

5 out of 5 average rating, 12 reviews

Cranberry Cottage

A picturesque property where your family or friends can relax and unwind. Explore Sydney, North Sydney, Louisburg, Baddeck, Ingonish and the Highland’s/Cabot Trail. Enjoy your morning coffee as seals bob around in the Atlantic just off shore or as the ferry sails to and fro NFLD. It's quiet, relaxing, pretty and bright. Nearby amenities include Coffee Shops, Groceries and NSLC. North Sydney and Sydney both a short drive. Enjoy world class restaurants serving fresh seafood all year round.

Top guest favorite

A modern country home is presented with a sloped roof and large windows. Surrounded by greenery, a stone pathway leads to the entrance. Outdoor seating is visible on a wooden deck, along with a grill, creating an inviting space for relaxation.

Cottage in Groves Point

4.98 out of 5 average rating, 90 reviews

Robyn’s Nest, where modern meets country

Come enjoy the Robyn’s Nest! Your modern country home away from home. Enjoy a quiet evening by the fire and venture to the nearby beaches by day. In the evening you can enjoy local entertainment nearby. Or plan your excursion around our beautifully raw Cabot Trail!! The people are special and your stay will be special. We will help you in every way to enjoy your stay. The best places to eat and shop. Come relax worry-free at our private hideaway just two minutes from Trans Canada Highway:)

Top guest favorite

A spacious lawn leads to the calm waters of St. Ann's Bay, with a fire pit surrounded by colorful chairs on a gravel area. The sky is filled with clouds, reflecting warm hues as the sun sets over the landscape.

Home in Englishtown

4.95 out of 5 average rating, 78 reviews

Seaside Cabot Trail Retreat

Escape to our oceanfront paradise in St. Ann's Bay on the scenic Cabot Trail! This brand new, spacious 2-bed home offers modern design and open concept living. Sleeps 6 with a queen bedroom, a bedroom with bunk beds (double on the bottom and single up top) and a pull-out sofa. Enjoy stunning sunsets, mountain views, and easy access to sightseeing, hiking, boat tours, and restaurants. Immerse yourself in the charm and beauty of Cape Breton, & create unforgettable memories during your stay.

Top guest favorite

The tranquil scene captures the homestead reflected in calm waters, framed by lush greenery. The house features a traditional design with a sloped roof and front porch, nestled among trees, providing a serene view of the surrounding landscape.

Home in North Sydney

5 out of 5 average rating, 70 reviews

Waterfront homestead on 4 landscaped acres.

Balmor Landing provides a charming Cape Breton experience, staying in a 150 year old Nova Scotian homestead property. Tucked away on 4 rambling acres of private, landscaped gardens, complete with apple, cherry and plum orchards, goldfish pond, large front & rear wooden decks, fire pits, and 100 feet of private rugged coastline overlooking a calm ocean inlet, It’s the perfect spot for kayaks, canoes and other water sports. (For a full house tour on social, IG @balmor_landing)

Guest favorite

A well-appointed bedroom features a spacious bed adorned with a blue and white floral duvet. A bedside table with a lamp is positioned next to the bed, and a window allows natural light to enhance the room's soft tones.

Guesthouse in Sydney

4.93 out of 5 average rating, 121 reviews

Comfie Place

This is a centrally located Airbnb located just minutes from the ocean. The Fortress of Louisbourg is just 30 mins away. The Cabot Trail is not far away with great beaches and epic scenery. Newfoundland ferry is 15 mins away. Comfie place is an open concept 1 bedroom unit with all amneties of home. Washer & dryer included. The queen size bed is extremely comfie with a nice duvet. Firepit, patio table and lawn recliners there for your use. Wireless internet & bell cable tv .

Guest favorite

The kitchen features a combination of light cabinetry and dark countertops, enhanced by recessed lighting. A small dining table with white chairs occupies the center, while modern appliances, including a refrigerator and stove, are conveniently situated. A ceiling fan provides additional comfort.

Guesthouse in Sydney

4.86 out of 5 average rating, 159 reviews

BlueJay Haven in Sydney River. $115 Per Night!

Private one bedroom suite with full kitchen and laundry facilities located in the heart of beautiful Cape Breton Island. 5 minutes from downtown Sydney, this home away from home, is conveniently located for day trips to the Fortress of Louisbourg, the world renowned Cabot Trail, the Bras d’or Lakes, etc. BlueJay Haven boasts a private entrance with parking as well as a private deck with barbecue. Escape to BlueJay Haven and “Your Heart Will Never Leave”.

Guest favorite

A quaint guesthouse is set in a green lawn, featuring a covered front deck with white railings. The exterior is painted white with light gray trim, and potted plants add touches of greenery. Large windows allow natural light into the space.

Cottage in Point Edward

4.88 out of 5 average rating, 495 reviews

Point Edward Guesthouse

Our cozy guest house is located along the Point Edward Highway, but don't let the name of our street discourage you from staying. It is a lovely, quiet, rural setting, along the shores of Sydney Harbour. Very centrally located between the city of Sydney and surrounding towns. The view is calming, and can be enjoyed on the covered front deck. Be sure to catch one of the stunning sunsets during your stay!

Guest favorite

A designated parking spot features a painted yellow sailboat design on the asphalt. The background shows a light-colored two-story building with front steps leading to the entrance, surrounded by green grass and trees.

Apartment in North Sydney

4.84 out of 5 average rating, 67 reviews

Coastal Sleepy Community

This little community is the gateway to Newfoundland Simple and easy going. The weather is always an acceptable topic, because it is always changing. So ask a stranger about the weather and you will be strangers no more, plus they will be sure to give you a smile when you do.