Vacation rentals in Chester

Chester Oceanfront Luxury Villa

Welcome to Skipper Hill, where you will find this stunning villa nestled in the corner of the community, on a 178' oceanfront lot! Enjoy being 10 minutes from both SENSEA Nordic Spa, and Chester Village - where you'll find a selection of restaurants, cafes, and shops sure to please any discerning traveller. Our villa was professionally built and decorated in 2020, thoughtfully prepared for both short and long stays. You'll love the uninterrupted ocean views, countless windows capturing the ocean

Charming Chester cottage steps from Nordic spa

Monthly + weekly discount available No HST (tax) on stays over 30 days A restored century-old east coast cottage steps away from the Rum Runners nature trail. A quick walk to a serene lakeside Nordic spa, as well as Chester village pubs, restaurants, shops, yacht club + saltwater pool overlooking the ocean on Nova Scotia’s coveted South Shore. Peggy’s Cove, Mahone Bay+ Lunenburg are nearby, as are poular golf courses + glorious beaches. Halifax is 50 minutes away. Registration: STR2526D8211

Lakefront Tiny Home ~ Hot tub

Lakefront access and water views with stunning sunsets greet you from the hot tub! Spacious and bright, this tiny home features: -Queen bed loft 🛏️ -Pull-out sectional with queen-sized sleeping area 🛋️ -Stocked kitchen with full-size appliances 🧑‍🍳 -3 piece bathroom with shower 🚿 -Deck for enjoying water views and sunshine ☀️ -Beautiful quiet lake 🌊 Only 10 minutes to the tourist hub of Mahone Bay, and 15 minutes to Lunenburg! Discounts when booked with the cottage on the property.

Sleep in the clouds. 30 feet in the air with hotub

Perched high on an ocean hillside, built on 30 ft tall steel legs, the cozy quarters above are akin to an old ship’s cabin. With 360 views at 30ft up you can chart the sun and stars across the sky, set your rhythm to the ebb & flow of the tide and scout the surf from above. Greet the evenings with a cozy woodstove, sunset with drinks on the deck, moonrise with a dip in the hottub & mornings with fresh espresso. Permit yourself to depart land for a while and come stand watch at The Tower.

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.

Moss Cottage on the Lake

Moss Cottage can be your getaway only 45 minutes from Halifax and a few kilometers from the village of Chester on Nova Scotia's beautiful south shore. It's your choice to take in the many local sights, shop in towns and villages that dot the coastline, sail, play golf or stretch out on any number of beaches -- all within easy driving. Or, perhaps you'd prefer to stay put at Moss Cottage for a lovely chance at solitude and a dip in our crystal clear, spring fed lake.

Breathtaking Oceanfront Chateau

Tranquility awaits at 'Harbour Mist' on the Aspotogan Peninsula w/ 192ft of private oceanfront. This stone & timber chateau was constructed by the finest craftsmen in 2015 w/ unique, luxurious materials curated globally. She sleeps 10 guests in 5,556 square ft over 3 levels; featuring 5 wood and propane fireplaces inside & out, breathtaking spiral staircase, geothermal heat/AC, lighted apple grove, & 2 master bedrooms. The most unique stay in Atlantic Canada!

The Cabin at The Woodlots

The Cabin at The Woodlots is located minutes from the Atlantic Ocean in the seaside community of Chester Basin. Our modern cabin is surrounded by acres of Acadian forest with stunning views of the natural landscape in all directions. A large wood-fired/electric hybrid hot tub is tucked in out front, while Adirondack chairs and a fire pit provide the perfect place to relax and keep warm in between soaks. Tranquil Croft Lake is a short stroll through the woods.

Waterfront loft with million dollar view- Suite 2

These unique and thoughtful suites, each of the three units are outfitted with subtle nuances giving the spaces their own special feel. Visitors will enjoy designer micro-kitchens, fully stocked with amenities any food enthusiast would appreciate. A cozy wood stove for those chillier evenings. All units have a special secondary sleeping nest area accessible by ladder. A serene place to hide away and watch for shooting stars through the skylight windows.