Holiday houses in Chester

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Top-rated holiday rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
An open-plan living area features a cozy sofa with decorative cushions, a wooden coffee table, and a bar-like seating area with tall stools. Stairs lead to a lofted sleeping area, and large windows provide natural light, highlighting the rustic wooden finishes throughout the space.
Tiny home in Lunenburg
4.98 out of 5 average rating, 401 reviews

Birch tree abode-Bunkie with dry/wet CEDAR SAUNA

Welcome to ‘Birch Tree Abode’. A unique way to unwind after a day in lunenburg county.Situated between Lunenburg and Mahone bay. Minutes from either. This bunkie’ is situated amongst the trees, with comfortable deck to enjoy the beginning/end of your adventures around the South Shore. A beautiful open plan living space, high end bathroom, all rustically finished . 400sq ft-this is slightly larger than a ‘tiny home’, however minimal space 4 storage/luggage ,also note 5.10 ceiling in bedroom area

Guest favourite
A spacious great room features large windows, allowing natural light to fill the space. A central fireplace with a wooden mantle serves as a focal point, complemented by soft seating arrangements including a light-colored sofa and a blue accent chair. Light-hued curtains frame the windows, providing a calming atmosphere.
Villa in Chester
4.93 out of 5 average rating, 146 reviews

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

Top Guest favourite
A serene lakefront scene captures vibrant autumn foliage reflecting on still waters. A wooden boardwalk leads to a small dock, surrounded by trees displaying shades of red, orange, and green, creating a peaceful natural setting.
Guest suite in Hubbards
4.96 out of 5 average rating, 275 reviews

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, or currently the snow banks ❄️ We are scent free & all natural with 100% cotton bedding Your stay includes a DIY Breakfast bar: Pancakes, syrup, rolled oats & oatmeal pkgs & of course coffee and tea Studio Suite is an Apartment here in our main building, more detail ⬇ TT, IG & FB: covecottageecooasis

Top Guest favourite
The cabin's exterior is framed by trees, illuminated by warm interior lights that reflect off large windows. A spacious wooden deck is visible, featuring two red chairs positioned towards the inviting entrance. The structure showcases a triangular gabled roof and a charming mix of wood siding.
Cabin in LaHave
4.97 out of 5 average rating, 882 reviews

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!

Top Guest favourite
A charming boathouse is positioned on a wooden dock, surrounded by lush greenery. The elevated deck features a glass railing, offering unobstructed views of the water. Two wooden benches provide seating, inviting relaxation in the serene seaside setting.
Cottage in Chester
4.95 out of 5 average rating, 111 reviews

The Boathouse on Scotch Cove

This little boathouse sits right on Scotch Cove in East Chester, NS. Enjoy seaside views from every angle, with lovely outdoor seating and propane BBQ. The deck leads directly to the dock allowing for easy access for swimming or watercraft provided. The place is just a short walk from hiking and biking trails, with nearby lakes and sandy beaches. The indoor projector and screen make movie nights so much better! The boathouse is fully equipped for winter with a cozy woodstove.

Top Guest favourite
Home in Chester Basin
4.96 out of 5 average rating, 160 reviews

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.

Guest favourite
Three dark, modern structures are set along the water's edge, featuring sharp angles and a metallic roof. Soft evening light reflects off windows, contrasting with the surrounding natural landscape. A smooth gravel path and plantings in the foreground enhance the tranquil setting.
Chalet in Lunenburg
4.89 out of 5 average rating, 292 reviews

Waterfront loft with million dollar views- Suite 1

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.

Top Guest favourite
Home in Lunenburg
5 out of 5 average rating, 151 reviews

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.

Superhost
A geodesic dome is positioned on a wooden deck, surrounded by gravel landscaping and natural stone accents. Sturdy steps lead up to the dome entrance, while tall trees are visible in the background, contributing to the serene, forested setting.
Dome in Chester
4.89 out of 5 average rating, 320 reviews

Norse Geodesic Retreat (Freya)

Experience the epitome of relaxation and luxury at Norse Geodesic Retreat. Nestled amidst nature's embrace, our distinctive geodesic domes offer an unrivaled escape from the hustle and bustle of everyday life. Step into a world of elegance and tranquility as you gaze through floor-to-ceiling windows at the breathtaking views outside. Unwind on your private deck, where a rejuvenating soak in the hot tub awaits under the starlit sky.

Top Guest favourite
The exterior of the architecturally unique cottage is showcased in the twilight. The structure features large windows and a sleek design, elevated on supports. Surrounded by natural landscapes, two chairs are positioned on the deck, offering a space to enjoy the views.
Home in Terence Bay
4.89 out of 5 average rating, 247 reviews

Back Bay Cottage

Designed and built by architect Peter Braithwaite, the unique cottage design offers an exclusive and tranquil getaway. Accommodating up to 6 guests, this open concept, fully equipped cottage is ideal for couples, small families or outdoor enthusiasts any time of year. The airbnb is located 20 minutes outside of Halifax on six-acres with an outdoor fireplace, BBQ and stunning views that overlook Back Bay.

Top Guest favourite
A large dining area features a wooden table surrounded by black chairs, set against expansive windows overlooking the water. Sunlight floods the room, highlighting the serene view of the lake and distant shoreline.
Home in Mahone Bay
4.95 out of 5 average rating, 248 reviews

Lovely oceanfront home w/4 BR + stunning views

Enjoy our lovely and spacious oceanfront home with port views to the iconic churches of Mahone Bay and starboard views past Strum Island to the open ocean. Sailboats bob at anchor just beyond our decks. Stroll out the back door to reach cafes, bookstores, the brewpub, village pub, restaurants and civic marina all within minutes. We pay diligent attention to cleaning protocols for your safety.

Top Guest favourite
A spacious living area features a large triangular window wall offering panoramic views of the ocean and surrounding trees. A comfortable couch and a rustic wooden coffee table are positioned near a cozy wood stove. A window seat, adorned with soft pillows and a throw, invites relaxation.
Cottage in Chester
4.99 out of 5 average rating, 140 reviews

Peaceful 2-Bedroom Coastal Cottage with Hot Tub

High above the ocean, this contemporary two-bedroom cottage provides sweeping coastal views, stunning sunsets, and a canopy of starry skies. Overlooking the entrance to Deep Cove, and out towards Chester, Nova Scotia, this secluded four-season cottage offers an idyllic escape, ideal for a romantic couple's getaway or a tranquil retreat from the everyday.

Popular amenities for Chester holiday rentals

When is the best time to visit Chester?

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Avg. price$196 AUD$198 AUD$185 AUD$203 AUD$211 AUD$259 AUD$294 AUD$350 AUD$266 AUD$255 AUD$203 AUD$257 AUD
Avg. temp-6°C-6°C-2°C4°C10°C14°C17°C17°C14°C9°C4°C-2°C

Frequently Asked Questions

  • What are the best places to stay in Chester?

    Vacation rentals are found throughout Chester’s residential neighborhoods, near the waterfront, and close to shops or parks. Visitors often choose homes with unique architectural styles or those surrounded by natural scenery.

  • What are the best things to do in Chester with kids?

    Kids can enjoy building sandcastles on local beaches, visiting playgrounds, or exploring nature trails near Chester. Families also participate in community art workshops, water sports, and historic walking tours.

  • What are some of the best things to do in Chester?

    Explore local art galleries, stroll Chester’s harborfront, or join boat tours showcasing maritime traditions. The village has seasonal theatre productions and markets with crafts and local foods.

  • How is the weather in Chester?

    Chester has cool springs around 21–37°F (-6–3°C), mild to warm summers at 47–67°F (8–20°C), and early autumn days near 48–67°F (9–19°C). Rain is common throughout the year, so a waterproof jacket is useful.

  • When is the best time to visit Chester?

    Late spring to early autumn is often recommended for milder temperatures and outdoor events. Summer brings sailing activities and community celebrations, while autumn highlights changing foliage and quiet village ambiance.

  • What are the best places to visit in Chester?

    Explore Chester's waterfront, visit small art galleries, and stroll through historic streets lined with wooden homes. The harbor area, nearby beaches, and artisan shops are frequently suggested for visitors.

  • What are some hiking trails in Chester?

    Chester has scenic walking and hiking trails along the shoreline, through wooded areas, and in nearby parks. Locals often suggest coastal paths for ocean views and gentle terrain suitable for most abilities.

  • What are some family activities we can do in Chester?

    Families in Chester can visit sandy beaches, rent kayaks for calm waters, or join community theatre shows. There are playgrounds, picnic spots, and guided walking tours highlighting local history and nature.

  • What are some of the best day trip ideas from Chester?

    You can explore historic coastal villages, visit artisan workshops, or hike through nearby protected forests. Smaller communities around Chester have lighthouse tours, traditional markets, and nature trails for adventurous travelers.

  • Are there any pet friendly accommodations available in Chester?

    Pet friendly vacation rentals are available in Chester neighborhoods, with homes that welcome dogs and sometimes cats. Look for stays near parks or green spaces, making walks and outdoor adventures easy to enjoy.

  • What are some local tips for visiting Chester?

    Locals suggest checking the tides before planning beach walks and visiting markets for handmade goods and produce. Bring a camera to capture Chester’s colorful waterfront, and chat with residents for insights on town history and current events.

  • What is Chester known for?

    Chester is recognized for its sailing heritage, picturesque harbors, and charming village ambiance. It is also noted for arts communities and historic wooden architecture dating to the region’s early settlement.

  • What are the best hidden gems to explore in Chester?

    Explore tucked-away beaches, scenic walking paths, and small art galleries in Chester. The area has secret gardens, local craft shops, and historic homes open for occasional tours.

  • What are the best foods to try in Chester?

    Locally sourced seafood is often recommended, including scallops, mussels, and lobster. Chester also has bakeries known for fresh breads and sweet treats, along with restaurants serving Nova Scotia specialties like seafood chowder.

  • What should I bring for a trip to Chester?

    Pack layered clothing to adapt to changing weather, a rain jacket, and comfortable walking shoes. If visiting in summer, bring sun protection, and consider swimwear for water activities around Chester's harbors.

  • What is the nightlife in Chester like?

    Nightlife in Chester revolves around cozy pubs, waterfront bars, and occasional live music events. Many places foster a relaxed atmosphere, inviting locals and visitors to enjoy conversation, maritime-inspired cuisine, and drinks.

  • What are the most popular events or festivals in Chester?

    Chester is known for summer theatre performances, art fairs, and sailing regattas around late summer. During these seasonal gatherings, the village welcomes visitors to local markets, craft shows, and community celebrations.

  • Are there family friendly vacation rentals in Chester?

    Chester has vacation rentals suited for families, including homes with extra bedrooms, gardens, or easy access to parks and beaches. You will find spaces in residential neighborhoods where families can enjoy quiet evenings and explore local attractions together.

Quick stats about holiday rentals in Chester

  • Total holiday rentals

    Explore 50 holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at $71 AUD per night before taxes and fees

  • Verified guest reviews

    Over 1,590 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Chester holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chester rentals

  • 4.9 Average rating

    Chester stays are highly rated by guests—averaging 4.9 out of 5!

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