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Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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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, 151 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

Superhost
An open-concept living area showcases a blend of rustic and modern design elements. A wood stove stands beside a large window, allowing natural light to fill the space. Two chairs and a small table create a cozy nook, complemented by sleek cabinetry and polished wooden floors.
Cottage in Martins Point
4.94 out of 5 average rating, 215 reviews

OTW Close 2 Nordic Spa — Accepting Travel Nurses

• "Occupancy Fees or Property use tax" are local sales taxes charged by Airbnb (HST 15%) • 3pm Checkin • 15 mins to NORDIC Spa • 10 mins from Mahone Bay & Oak Island • Free bikes with access to the Chester Connection Trail • BBQ, full kitchen and utensils, A/C, cable TV, wifi and parking • Open-concept living • Full bath on the main floor, 2 bedrooms on the second floor • The house is 100 years old so the stairs are steep • Porch has shared laundry facilities for the guesthouse next door

Top guest favourite
A spacious living area features large, angled windows with views of the ocean and surrounding trees. A central wooden coffee table is positioned between two seating areas, one with a dark leather sofa and another with a cozy armchair. A modern fireplace adds focal interest.
Cottage in Hubbards
5 out of 5 average rating, 56 reviews

Seafarers Hideaway

Welcome to Seafarers Hideaway! This 800 sq. ft., Scandi‑inspired vacation home overlooks St. Margarets Bay. Located 10 minutes from Bayswater Beach, 20 minutes from Hubbards, and 30 minutes from Chester. This quiet and private retreat is tucked away 2 km off the Lighthouse Route Hwy 329 and offers incredible ocean views, along with access to a private cove and beach. It is truly a place where time stands still, allowing for rest, rejuvenation, creativity, and meaningful memory‑making.

Superhost
A geodesic dome is illuminated softly from within, surrounded by an expansive grassy area under a starlit sky. The structure features large triangular windows, offering a clear view of the interior. Nearby trees frame the scene, enhancing the feeling of privacy.
Dome in Rose Bay
4.88 out of 5 average rating, 152 reviews

Glamping Dome 1 SeaSpray

Welcome to Board & Batten in beautiful Rose Bay, Nova Scotia. Sitting on a cliff overlooking the ocean, this breathtaking property is home to four, individually rented, geodesic glamping domes and two premium cottages Each identical dome offers a breathtaking view of the ocean and the night sky, as well as everything you’ll need for a luxury stay (this isn’t camping, it's glamping!). The domes and cottages are set nicely apart to allow a feel of privacy.

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
4.9 out of 5 average rating, 296 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, 159 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.

Guest favourite
The exterior of a modern home is shown at dusk, with a vibrant sunset illuminating the sky in shades of pink and orange. A spacious deck extends from the house, featuring seating arrangements for relaxation, while a field of wildflowers occupies the foreground.
Home in LaHave
4.97 out of 5 average rating, 102 reviews

The Lookout - Cottage

Luxury modern home with incredible ocean views. Just under 1,000 sq. ft. on 2 acres of land, The Lookout has been meticulously designed with a chef's kitchen, gas fireplace, heated bathroom floor, SmartTV, Wifi and some of the best views on the South Shore. The Lookout is ideal for a family, couple's getaway, girls weekend and anyone wanting to explore the natural beauty of Nova Scotia. We also welcome pets!

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, 257 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.

Guest favourite
A sauna space features warm wooden walls and benches, creating a serene environment. Natural light filters in through a large window, illuminating a small basket of stones. The simplicity of the design emphasizes a calming retreat for relaxation.
Home in Hubbards
4.9 out of 5 average rating, 119 reviews

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.

Guest favourite
Two colorful kayaks, one in vibrant red and orange and the other in white with blue accents, are positioned on the grassy area beside a modern cottage. The structure features large glass windows and a curved roof, allowing natural light to fill the interior.
Home in Chester
4.94 out of 5 average rating, 77 reviews

Endeavour Cottage

Take it easy at this unique and tranquil getaway. Enjoy your stay in our private lakefront cottage that’s only a short walking distance to the heart of Chester to explore local shops and restaurants. The Nordic Spa, Golf Club, Yacht Club and Beach are only minutes away. We are nestled in a hidden peaceful yet central location making our cottage the perfect getaway for all!

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 Deep Cove
4.99 out of 5 average rating, 151 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.

Guest favourite
A tranquil lakeside setting is depicted at sunset, showcasing vibrant colors reflecting off the calm water. A wooden bench sits nearby, framed by trees. A small dock extends onto the lake, adding to the serene atmosphere of the natural surroundings.
Guest house in Chester Basin
4.86 out of 5 average rating, 158 reviews

Hutt Lake Studio 10 minutes away from Sensea Spa

Relax and unwind at this unique and tranquil getaway. Air conditioned for your comfort. Steps away from a lake for you with private beach to enjoy. Kayaks and pedalboat for you free to use at your own risk. Central location with Mahone Bay, Lunenburg, Peggy’s Cove and Halifax all a very easy drive from your cottage. Very quiet and peaceful location.

Popular amenities for Chester holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Chester's top sights

Chester Golf Club

43 locals recommend

Chester Playhouse

29 locals recommend

Graves Island Provincial Park

18 locals recommend

Other great holiday rentals in Chester

Top guest favourite
The cottage is set against a backdrop of the ocean, with views of distant islands visible on the horizon. Lush greenery surrounds the area, while the clear blue sky adds to the tranquil atmosphere. The scene reflects a serene coastal environment.
Home in Chester
5 out of 5 average rating, 29 reviews

The Little Bird Cottage

Superhost
The modern Corten steel exterior of the two-storey Gate House reflects a harmonious blend with the surrounding landscape. Soft lighting emanates from the large windows, illuminating the interior spaces. A fire pit is situated outside, complemented by nearby wooden seating.
Cottage in Lunenburg
4.9 out of 5 average rating, 71 reviews

2-storey designer cottage - Shobac Farm Gate House

Top guest favourite
A Scandinavian-style retreat is showcased with a striking design, featuring large glass windows and a well-furnished oceanfront deck. A sauna and hot tub are positioned nearby, with lounge chairs set on the grass, enveloped by trees and a tranquil evening sky.
Home in Pleasantville
5 out of 5 average rating, 27 reviews

Zen Oceanfront Chalet- Hot Tub & Sauna

Superhost
A spacious living area features large windows that invite natural light and offer views of the outdoor landscape. A modern staircase spirals upward, while wooden flooring adds warmth to the room. A cozy seating arrangement complements a contemporary fireplace and decorative elements.
Cabin in Mahone Bay
4.83 out of 5 average rating, 134 reviews

The Narrows Nest

Top guest favourite
A modern kitchen is presented with blue cabinetry and a white farmhouse sink. Grey brick walls add texture, while a stainless steel range and hood complement the space. A rustic wooden dining table is set with chairs, creating an inviting area for meals.
Home in Hubbards
5 out of 5 average rating, 37 reviews

The Twee House at Meisners Beach

Top guest favourite
A modern Nordic-style cabin is nestled among trees, featuring large windows that offer views of the surrounding greenery. A spacious deck extends from the cabin's entrance, complemented by a barbecue grill and a firewood stack nearby. Vibrant greenery and wildflowers blanket the foreground.
Cabin in Brooklyn
5 out of 5 average rating, 30 reviews

Brooklyn Shore Lodge

Top guest favourite
A circular hot tub is positioned on a deck overlooking the water. Clear blue skies and scattered clouds are visible above a calm water surface. Comfortable outdoor seating is arranged nearby, creating a tranquil setting for relaxation and enjoyment of the beautiful waterfront view.
Bungalow in Lunenburg
4.92 out of 5 average rating, 92 reviews

Oceanfront #6 Hot tub sun sets huge deck BBQ 2 bed

Guest favourite
A newly renovated kitchen features light-colored cabinetry with a mix of green and natural wood tones. A farmhouse-style sink is centered beneath a window, illuminated by natural light. Hexagonal tiled flooring adds texture to the space, with modern light fixtures enhancing the design.
Cottage in Chester
5 out of 5 average rating, 30 reviews

Marigold Cottage - 7 bdrms in Chester Village

When is the best time to visit Chester?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$230 SGD$232 SGD$231 SGD$181 SGD$188 SGD$231 SGD$263 SGD$312 SGD$237 SGD$227 SGD$181 SGD$230 SGD
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 40 holiday rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at $76 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,660 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Chester holiday rentals include wifi 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!

Destinations to explore

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