Holiday houses in Chester

Luxury Tiny Home Retreat w/ Hot Tub Near Chester

A Modern Shipping Container Retreat Tucked away in Chester NS walking distance from nine mile lake, this sleek and stylish tiny home offers big comfort in a compact space. Featuring a cozy interior, outdoor seating, and all the essentials for a peaceful getaway. Unplug, unwind and experience container living like never before. ☆ Brand New Shipping Container 320 sqft tucked away in Chester NS. Nordic spa, Ski Martock, golf ☆ Hot tub ☆ Fully equipped Kitchen, Tea and coffee ☆ Wifi ☆ Large TV

Half Moon Cove Retreat

Welcome to Half Moon Cove Retreat, your peaceful escape on the shores of beautiful Chester, Nova Scotia. This charming beachfront retreat offers the perfect blend of comfort, privacy, coastal charm, and convenience—just steps from the ocean and complete with a private pool. Inside, you’ll find cozy coastal décor, a fully equipped kitchen, and spacious living areas. Spend your days lounging by the pool, swimming the calm waters, or exploring the picturesque village of Chester - Nordic Spa & Golf.

The Whale House

The Whale House offers bright panoramic water views from every room. Located in the beautiful Village of Chester steps away from marinas, eclectic restaurants, artisan shops, beach, and yacht club. Open concept with large deck to eat and enjoy the stunning views of sailing boats. Well appointed and beautifully decorated with fireplace and comfy furniture. Three large bedrooms, 2 full baths (one upstairs and one downstairs), fully equipped chef style modern Ikea kitchen. A true place to harbour.

Storybook coastal farmhouse with ocean access

Live the seaside dream in this beautifully decorated and generously equipped Cape Cod home. Nestled in a picture postcard setting just outside the Village of Chester, this oasis is the perfect home base to enjoy all Nova Scotia's storied South Shore has to offer. Just a short walk down a tree-lined lane you can picnic and swim off a shared oceanfront wharf. Come home to whip up a feast in the well-stocked kitchen, then settle in for a game of pool or evening by the fire –either inside or out.

Beautiful home in picturesque Chester NS

Kick back and relax in this calm, stylish space. Newly renovated and stylishly decorated, this 4 bedroom home is in the heart of beautiful South Shore NS in the lively and picturesque town of Chester. Close to beaches, golf, Sense Nordic Spa, Trans Canada Trail and lots of little shops and restaurants. Only 40 minutes from Halifax, an hour from the airport and 30 minutes for Lunenburg/Mahone Bay. Fully set up for a wonder gathering of family and friends with lots of space for everyone.

Marigold Cottage - 7 bdrms in Chester Village

Bring the whole family to the newly renovated Marigold cottage with lots of room for fun! Situated steps away from everything Chester has to offer, this fully renovated 150 year old home allows plenty of room for a large group. There are several sitting/living rooms on the main level as well as a beautiful new kitchen with a large island. The original wood flooring has been restored throughout and the bathrooms have been thoughtfully modernized. There are 7 bedrooms and 2.5 bathrooms.

White Cottage

White Cottage, synonymous with endless charm, true grace and elegant oceanfront living since 1795. One of the original homes in Chester village and most recently remodelled by renowned designer Philip Mitchell, it is currently recognized as one of the most beautiful & highly awarded homes in Atlantic Canada. Featured on covers and detailed in the pages of sophisticated magazines across the globe, our Nova Scotian landmark is now ready for you to add the next chapter to it’s story.

Chester Basin Vacation Retreat Oceanfront

This cottage is located in Chester Basin, Nova Scotia. Along the world famous lighthouse scenic route 10 minutes from Chester Golf Course Chester Yacht Club and Marina Mins to beaches Bike Trails World famous Oak Island 54 mins to Peggy's Cove Lighthouse 24 mins to Lunenburg Heritage Site and Home of the BlueNose Tall Ship 42 mins to metro Halifax 57 mins to Halifax International Airport 18 mins to World Famous Shore Club Lobster Hall and live music 1 hour to Alyesford Zoo

The Oasis on Blueberry Lane

Welcome to your private lakefront escape in Chester Grant. Swim from the dock on a warm, swimmable lake, paddle at sunrise, and soak in the hot tub beneath star-filled skies. Gather around indoor and outdoor wood fires in every season, then head inside for pool tournaments and spacious, comfortable living designed for connection and relaxation. Just 10 mins to Sensea Nordic Spa and 30 mins to Ski Martock, the perfect four-season retreat for families and friends year-round.

Oceanfront #6 Hot tub sun sets huge deck BBQ 2 bed

Nate’s Nest is super close to the Historic town of Lunenburg Huge deck outdoor living Hot tub, Sun Sets Waterfront Ocean views quite charming unit with 2 baths modern kitchen & Den for friends to visit. HOOKd home Nestled in a very rare community lil HOOK Properties inclusive of a private pier boat launch and like minded people who enjoy living on the water A water lovers dream Wake up to sparkly water shimmering into your windows or enjoy star gazing in the hot tub.

Ocean Front #3 HotTub Sunset RoofTopDeck BBQ 2bath

Waterfront Cottage: Huge deck, sun sets, Private Hot Tub: 6 Person tub for 2. Panoramic Water Views: Modern Cabin: privacy and a peaceful environment. Large Deck: outdoor living space both you can take in the sun or retreat into the share. Nature Retreat with wildlife Romantic Escape: for couples, Heated floors, Shower tower, queen master, an extra guest could sleep on the couch. Super private chefs kitchen. Well equipped for all seasons.

The Cabin at The Woodlots

Save 25% on 2-night stays Monday–Wednesday, Oct–Apr. The Cabin at The Woodlots is a private modern retreat surrounded by acres of Acadian forest in Chester Basin. Enjoy a large wood-fired/electric hot tub, indoor fireplace and outdoor fire pit, with Croft Lake just a short stroll away. Ideally located between the seaside towns of Chester and Mahone Bay, with the Atlantic Ocean, trails and the best Nova Scotia's South Shore at your doorstep.