Holiday rentals in Chester

Home in the Heart of Chester

Newly renovated charming home centrally located in the historic Village of Chester, Nova Scotia. This property is only one block from the shops, pubs, galleries and restaurants of Queen and Pleasant Streets, 3 blocks from the Front harbour and Yacht Club. Want to enjoy the nearby Sensea Spa, but have no place to stay? We are a 4 minute drive to the Sensea Spa, and perfectly located in downtown Chester. Additionally, we are only 12 minutes to Oak Island, and 20 minutes to Mahone Bay or Lunenburg.

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.

Ocean Front #4 Hot Tub 2bdrm huge deck BBQ 2bath

- Oceanfront, Pier, Boat Launch, - Massive Deck: Ideal for lounging entertaining, dining, High-Top Table, BBQ, Firewall: Ensures safety and peace of mind. - Hot Tub: Unwind and enjoy the serene ocean views. - Kitchen: induction cooktop and wall oven, ideal for preparing gourmet meals. - Two Bedrooms, Two Baths: The home includes a spacious master bedroom with a king-size bed and an en suite bath. - Second Bathroom: tub for a relaxing soak. HOOKd 4 perfect retreat best of oceanfront living.

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.

Captain's Quarters - 2 bedroom harbourview condo

Located in the heart of sea-side Chester, Nova Scotia with a gorgeous, full view of the front harbour. The Captain’s Quarters is a bright and beautifully finished, spacious, 2-bedroom condo that is central to all that scenic Chester has to offer. Walking distance to the pubs, restaurants, bakery, yacht club & much more! Large, floor-to-ceiling windows offer a perfect view of Mahone Bay. Less than a 5-minute drive to Sensea Nordic Spa - a perfect home base for your South Shore stay.

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.

Spectacular 5 Bedroom Spaview Retreat!

Join us on Stanford Lake for your next getaway! This newly built retreat has a Scandinavian feel and overlooks a peaceful lake. Sprawl out on your king sized bed and take in the gorgeous views of Sensea Nordic Spa. Minutes from the Chester Yacht Club and Chester Golf Club. Chester Village, grocery stores, liquor store, bars and restaurants are all within walking distance. A short drive to many beautiful beaches, historic Lunenburg, Mahone Bay, Hubbards, and world famous Oak Island.

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.