Family-friendly holiday rentals in Chester

Stunning Island Home Above Treetops Near Lunenburg

SkyView on LaHave Island is car-accessible, built on the highest point of a gorgeous island like a castle on a hill. A 2-story atrium, multiple large windows and skylights reveal spectacular 360-degree views of picturesque coves, a sprawling bay and the vast Atlantic. Enjoy lounging outside on 3 decks with glass panels. High-speed Internet. 5 mins from Crescent Beach swimming, 7 mins from mainland activities on Lighthouse Route, 40 mins to Lunenburg. See our video on Youtube. A phenomenal spot!

Charming Ocean Retreat

Perched on a hill overlooking the Aspotogan Cove, this lovingly restored 150-year-old family home offers everything you might need for a relaxing peaceful retreat. The backyard opens onto four acres of trails - perfect for mountain biking and hiking - and Bayswater Beach, one of the exquisite beaches on the South Shore, is only five minutes away. The beautifully appointed chef’s kitchen invites culinary play, and an extensive collection of games, books and movies will keep you well entertained.

The Cosy Red Roof

situated between Mahone Bay/ Lunenburg! (4 min drive to Lun,7min drive to M.Bay) Step into the private entrance,you are welcomed to warm ,rustic decor to enjoy your coffee/breakfast. Private bathroom (toilet/shower) beautifully finished with chrome fixtures finish the downstairs. Upstairs,large bedroom,(queen bed)lazyboy sofa,tv ,with views of the woodland garden! (There is no ‘outside’ space for guests at this time) Heaps of character, this is an ideal setting to relax after time exploring !

The Oasis on Blueberry Lane

Enjoy swimming or kayaking in our beautiful lake. Afterwards, hop in the hot tub to relax your tired muscles, then roast marshmallows over the firepit or have a game of pool. You can also curl up next to wood stove for a lazy evening in. Take a short drive to one of the several stunning beaches. Enjoy being 10 minutes from both SENSEA Nordic Spa, and Chester Village - where you'll find Chester Golf Course, a selection of restaurants, cafes, and shops. Only 30 minutes to ski Martock!

Sailors’ Paradise - Stevens Cove Guest Quarters

Just steps from the wharf you'll find Stevens Cove Guest Quarters. The apartment is at ground level with a spacious deck overlooking the mooring field. The bay is dotted with boats in this very active sailing community of Chester - home to the largest keel-boat regatta in North America. Whether you are a sailor or just enjoy the water view this is the place to see boats large and small, modest and grand from May through October. The posted price includes 15% Harmonized Sales Tax.

Stunning Oceanfront near Halifax

This bright oceanfront chalet/cabin is secluded, quiet and all about nature, 20 minutes from Halifax. There are 2 bedrooms, 2 bathrooms, 2 floors with a deck right on the ocean. The chabet is open concept, modern, and finished with hardwood floors, copper accents and all the basic comforts. The location makes it ideal for hiking, yoga, relaxing and oceanfront living. The house is 1300 ft2. There is a heat pump for heating and cooling, the woodstove is not for guest use.

Cleveland Beach Cottage

Beautiful Cleveland Beach Cottage overlooking the ocean in St. Margaret's Bay with white sandy beach 250 yards away and outdoor hot tub for 2! Updated, clean and bright with new flooring in main areas and newly renovated bath 2025!. Large windows in great room with full water views of picturesque St. Margarets Bay. Enjoy the inspiring sound of rolling waves, amazing sunrises and colours of sunsets are reflected on the water. Smell the ocean breeze... New STR #STR2425D7182

Ocean View Loft Overlooking Harbour

Explore the unique UNESCO heritage town in this bright, loft style apartment. You won't miss any of the action sitting on the large, sunny deck overlooking Lunenburg Harbour & the Bluenose II. Whether it's the comings & goings of the majestic schooners; the dory or sailboat races; the arrival of new vessels which have come from afar; or simply the daily activity of the harbour; everything happens on the Bluenose wharf.

Beautiful ocean front couples getaway

A one bedroom self contained unit with full bathroom, kitchen, dining area, open/bright living room, with TV, internet, WiFi, & cable. Private entrance,parking, private courtyard with outdoor kitchen, beach and fire pit. A great place to relax or romantic getaway. A perfect well appointed unit perfect for two. Sit by the fire table or enjoy the ocean view.