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The places that never leave you.

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Book direct & have more money left for lobster.

We don’t think you should be charged to book your own vacation. The big booking engines are built on that idea and an array of plus, plus, plus fees. It all adds up to a whole lotta money for you and needlessly takes away from what you actually left to enjoy your vacation.

Here is some welcomed news - There are NEVER any booking fees, pet fees or change fees when you book direct at sleepyhouse.ca.

Our own secure booking platform allows you to confidently book your next stay, pay by credit card, add coverage and all with a potential savings of up to 35% in a fee free environment. It’s that easy.

Nova Scotia.

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- The South Shore -

Aerial view of a coastal area with trees, a small beach, and buildings near the shoreline, overlooking the ocean.

The Beacon
Bayswater Beach

Truly, a one-of-a-kind escape. 11 acres of oceanfront privacy and views unmatched across Nova Scotia. On a clear day, enjoy a long look across to Peggy’s Cove.

Your soft landing on a perfectly rugged South Shore coastline.

Sleeps 4

Oceanfront

Forested

View Cottage

2025 rates from $195/night

A covered porch overlooking a body of water with houses and trees, furnished with a white sectional sofa, pillows, a wooden coffee table with a lantern, and a stone fireplace with black lanterns.

White Cottage, 1795
Chester Village

Standing tall above the Chester front harbour since 1795, White Cottage is an world-renowned and highly awarded Nova Scotia icon.

Hosting exclusive groups and individuals year-round - this is where big moments are celebrated and memories are made.

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Sleeps 8

Oceanfront

Private Wharf

View Cottage

2025 rates from $595/night

Living room with white sofas, a beige armchair, a wooden coffee table with decorative vases, large windows, a wood-paneled ceiling, and a bookshelf with decorative items.

Witmere
Chester

Straight from the pages of a design magazine and inserted into your vacation dreams …

One-of-a-kind stylish masterpiece with unique moments at every turn. True vacation elegance …

Sleeps 8

Oceanfront

Private Gardens

View Cottage

2025 rates from $595/night

A bedroom with a bed, two nightstands, and a chair with a stuffed animal. The wall behind the bed is white shiplap, and the other wall is painted blue. There is a window with blinds, a picture on the wall, and a blue blanket on the bed.

The Nest
Deep Cove

Relax in oceanside peace. Exceptionally finished and fully-stocked for your South Shore adventures. Or, just sit and watch the boats in the cove and the eagles fish.

Relaxation at it’s finest.

Sleeps 6

Oceanview

Private Gardens

View Cottage

2025 rates from $195/night

Aerial view of a small harbor with boats docked, surrounded by lush green trees and residential houses, under a blue sky.

The Oaks Seaside Retreat
Chester Basin

An icon of the South Shore since 1898. Traditional inn that has been thoughtfully redesigned as a unique oceanfront retreat.

Big get-togethers, treasured family reunions or weekend getaways with your crew - we host it all.

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Sleeps 8

Oceanfront

Private Mooring

View Cottage

2025 rates from $595/night

Living room with wood flooring, white walls, a glass-top coffee table with a bird sculpture and books, beige sofa, blue cabinet, and an open dining area in the background with tables and chairs.

The Cupcake House
Old Town Lunenburg

Peaceful, proper and playful in the UNESCO World Heritage town of Lunenburg.

Live like a local and stay amongst all of the character and charm of Canada’s East Coast crown jewel.

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Sleeps 4

Historic Town

Private Gardens

View Cottage

2025 rates from $195/night

Aerial view of a coastal neighborhood with colorful houses, trees, a church, and a harbor with sailboats on calm waters.

Wandering Fox
Old Town Lunenburg

A character stay lovingly designed with travellers in mind.

A short & very scenic walk to take in all of that famous Old Town Lunenburg charm, from your home base on the hill.

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Sleeps 6

Historic Town

Private Gardens

View Cottage

2025 rates from $185/night

View of a lakeside with houses, boats, and colorful autumn trees under a clear blue sky.

The Back Harbour House
Chester

Not just ‘on’ the water, but ‘in’ the water! Incredibly unique ocean experience and with an interior to match this unforgettable setting.

The perfect home base when staying in is the game plan.

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Sleeps 4

Oceanfront

Private Wharf

View Cottage

2025 rates from $795/night

Bedroom with white bed, pillows, beige blanket, nightstand with lamp, windows with blue curtains, whale artwork, small dresser, and decorative pillow with house design.

Spyglass Seastead
Western Shore

An original South Shore Seastead, loaded with history and right around the corner from Oak Island.

This is the real treasure you have been after …

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Sleeps 8

Oceanview

Private Gardens

View Cottage

2025 rates from $269/night

A wooden dock extends into a calm lake at sunset with clouds and trees on the horizon.

Millet Lake House
Chester Grant

The ultimate South Shore lake house experience. Your own private sandy beach, dock, hot tub & finishes designed to impress.

As serene, splendid & unique as it gets.

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Lakefront

Sleeps 8

Forested

View Cottage

2025 rates & dates soon …

Open-concept living room and kitchen with white walls, large windows, and modern decor. Includes a dining table with six chairs, a kitchen island with bar stools, a white sofa, and a TV.

The Compass Cottage
Deep Cove

A seasonal retreat that truly is a treat. Surrounded by lush coastal gardens on one side and the ocean on the other.

Situated on one of the quietest little coves on Mahone Bay. Close enough to town, but a world away in serenity.

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Sleeps 4

Oceanview

Private Gardens

View Cottage

2025 rates from $195/night

Kitchen with white cabinets, stainless steel refrigerator, microwave, dishwasher, gas stove, wooden table and stools, view of water through large windows.

The Acorn at The Oaks
Chester Basin

The famous home of South Shore hospitality, just on a smaller scale. Weekday getaways have never been so classy.

Soaring views over pristine Chester Basin set the scene for a memorable stay.

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Sleeps 4

Oceanview

Private Gardens

View Cottage

2025 rates from $249/night

Bright bedroom with a white ceiling, chandelier, large windows with white curtains, a bed with white linens, patterned armchairs, a small wooden table, a fireplace with a painting above, and a doorway leading to another room.

The Coach House at White Cottage
Chester Village

A little slice of couples getaway bliss, positioned perfectly high atop the beautiful Chester front harbour.

Explore the village on foot and return home to all the romance of White Cottage. Couldn’t have it any better!

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Oceanfront

Sleeps 2

Private Gardens

View Cottage

2025 rates from $225/night

Aerial view of a coastal town with houses, trees, roads, marina, and water with boats and islands in the distance.

Pine Cottage
Chester

Spectacular setting and an absolutely lovingly cared for home, loaded with everything you need.

Tucked away on a private acreage on the outskirts of town. The peace and quiet you seek, with amenities not too far away.

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Oceanview

Sleeps 4

Private Gardens

Inquire

2026 rates & dates soon …

A calm river with trees along the shoreline under a blue sky with scattered clouds.

The Stanford Lake House
Chester

Year-round lakefront escape with unrivalled views across to the world famous SENSEA Spa.

Only minutes to town, but you won’t want to leave the perfectly designed indoor and outdoor space.

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Lakefront

Sleeps 6

Private Gardens

Inquire

2026 rates & dates soon …

- The North Shore -

Five houses with red and yellow roofs on a grassy hill, reflected in a calm body of water, under a partly cloudy sky during sunset.

Ocean Sunset Chalets
Brule Beach

This legendary North Shore beach escape at Brule Beach now works with Sleepyhouse. Yay!

Classic styling, cozy feels and the ultimate family beach experience at your doorstep. Remember when? That’s what OSC is all about.

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Oceanfront

6 Chalets

Beach Bum

Visit OSC …

rates from $295/night

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Prince Edward Island.

- The North Shore -

Modern kitchen with blue cabinetry, white countertop island, stainless steel refrigerator, stove, and hood, decorative white tiled backsplash, open shelves with plants and dishes, and wall art.

The Summerhouse
St. Peter’s Bay

A quiet escape with coastal finishes, fully stocked and plenty of room indoors & out for families to enjoy a perfect PEI experience.

Acreage overlooking majestic St. Peters Bay and a short bike down to the world famous beach and boardwalks at Greenwich National Park (PEI).

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Sleeps 8

Oceanview

National Park

View Cottage

rates from $279/night

Aerial view of a lakeshore with green fields, trees, and scattered houses under a partly cloudy sky.

Tidepost at Tracadie Bay
Blooming Point

The way island vacations used to be is the way they still are at Tidepost. Sandy beaches, salty air & always carefree family fun in the cutest little classic cottage.

Minutes to town but miles from humanity …