Family-friendly 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

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

The Bear’s Den treehouse lodging.

Nestled in the woods, accessible year round. Very private & quiet. No hunting on this property but enjoy great fishing. Pizza & burger take-out just 10 min away. Lots of water close by for kayaking/canoeing. ATV trails just a few km away. Firewood supplied. Please bring your own drinking / wash water. Pets welcome, but Not on the furniture unless you’ve brought a cover. Never leave pets unattended. No running water. Outhouse/toilet facility. Bring your own disposable propane tank if BBQ’ing.

East Coast charm, cabin and hot tub by the river

The perfect location to explore the very popular South Shore of Nova Scotia. Close to beaches, cafes, restaurants, charming fishing villages and many other amenities. Come for a magical getaway. Tucked away in the woods along side a babbling brook. Enjoy morning coffee on the deck, BBQ your dinner overlooking the river, groove to our vintage record collection, keep toasty by the wood stove and float in the hot tub under the stars. This is a wonderful cabin experience you won't forget!

Spacious Lakefront Cottage Retreat

This pet friendly, four season cottage is the perfect space to escape the city with a loved one for a weekend or for your next family vacation! Only 50 minutes from Halifax, it’s in perfect proximity between downtown Chester and Windsor. The home Includes a large eat in kitchen with sitting area, bathroom, laundry and two bedrooms on the main level and a walkout primary bedroom and large living room with wood stove on the lower level and a large walk out deck overlooking the lake.

Studio Apt at Cove Cottage Eco Oasis

Cove Cottage is a lakefront eco-retreat tucked into the woods, 45 mins from HRM. We vibe with nature. Walk the boardwalk, sit lakeside enjoying the views, feed the chickens, wander the gardens, go kayaking or swimming. We are scent free & all natural with 100% cotton bedding Your stay includes a DIY Breakfast bar: Pancakes, syrup, rolled oats & of course coffee and tea Studio Suite is an Apartment here in our main building, more detail ⬇ TT, IG & FB: covecottageecooasis

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.

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.

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.

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.

Koko Bay: Glamping, where glamour meets nature!

Escape the ordinary at KoKo Bay—an adults-only glamping retreat near Hubbards! Sleep in luxury, wake to ocean breezes, and stargaze by the fire. With epic views, fine linens, and direct access to Rails to Trails, it’s the perfect mix of wild and wonderful. Beach days, bike rides, and total unplugged bliss await. Romantic, peaceful, and unforgettable. (Yes, nature’s guests—bugs & critters—may drop by!!) it's part of the magic!

Nordic Tides Retreat Sauna & Spa

Welcome to Nordic Tides, where minimalist Nordic design meets Nova Scotia’s rugged coastline. This oceanfront retreat offers panoramic views, a private cedar sauna, hot tub, and fire pit. Perfect for slowing down, soaking in the sea, watching the sunrise over the ocean, and reconnecting with loved ones. Every detail is designed to create balance, beauty, and intentional living.