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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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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
4.97 out of 5 average rating, 393 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
4.94 out of 5 average rating, 143 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
The exterior of a cottage is surrounded by lush greenery and features a circular swimming pool. Colorful flowers and shrubbery line the walkway, leading to wooden lounge chairs and a shaded umbrella. A fire pit area is visible, inviting outdoor gatherings.
Tiny home in Nova Scotia
4.97 out of 5 average rating, 247 reviews

Cozy Cottage on South Shore. 30 min from Halifax!

A very cozy and peaceful place to base any vacation on the South Shore out of. Very close to hiking and ATV trails. No visible neighbors from the yard, lots of wildlife. Large parking areas. Interior is a mixture of new and re purposed materials. Appliances are small but functional, all the comforts of home but smaller. Double bed is incredibly comfortable. It is my home that I vacate for guests, and contains some sentimental decorations and items. RYA-2023-24-03271525339628999-1197

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, 875 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 welcoming porch is adorned with two light blue adirondack chairs, positioned to overlook a serene lake. The ground is covered in vibrant autumn leaves, and trees in the background are reflected in the calm water. The scene captures a peaceful outdoor retreat.
Cottage in Chester
4.96 out of 5 average rating, 175 reviews

Cozy Lakefront Cottage w/ wood stove near Martock

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.

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, 110 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
Two colorful adirondack chairs, one bright pink and one blue, are positioned on a wooden deck. A potted plant with vibrant flowers sits nearby, and a barbecue grill is visible in the background, enhancing the outdoor relaxation space.
Cottage in Chester
4.95 out of 5 average rating, 146 reviews

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.

Top Guest favourite
Home in Mahone Bay
4.97 out of 5 average rating, 223 reviews

Mahone Bay Ocean Retreat

Your luxury ocean getaway and private spa for two. Private beach access, keyless self check-in. On the beautiful South Shore minutes from town. Cathedral ceilings & epic views. Four seasons. Hot-tub, full spectrum infrared sauna, both indoor & outdoor rainfall showers. Indoor wet room with claw foot tub. Bbq, wireless wifi, chef’s kitchen, wine fridge, AC, wood stove, Netflix, and King size bed with premium linens. A calm, luxurious space flooded with natural light.

Top Guest favourite
A wooden deck extends from the cottage, featuring a covered seating area and several adirondack chairs. The cottage's exterior is a combination of wood and black panels, framed by lush greenery. A grill is placed under the shelter, ready for outdoor cooking.
Cottage in Lunenburg
4.98 out of 5 average rating, 126 reviews

A Secluded Lakefront Spectacle

Kick back and relax in this calm, stylish space. This lake side cottage is located minutes from the historic towns of Lunenburg and Mahone Bay. Regardless of which direction you go, there is an abundance of choices. Whether you enjoy outdoor activities such as beaches, hiking, off road and water sports, or would rather site see and dine out, this area offers it all. If relaxing while overlooking the lake is what you would prefer then this is the perfect setting.

Top Guest favourite
A bright bedroom features a comfortable bed adorned with a colorful quilt. Two windows allow natural light, while built-in shelves display books. A vintage blue trunk is positioned at the foot of the bed, with soft lighting from two bedside lamps creating a cozy environment.
Apartment in Mahone Bay
4.88 out of 5 average rating, 123 reviews

Pleasant Street Suite

Location, location, location! This studio apartment is located in the heart of Mahone Bay. Restaurants, shops, grocery store, pharmacy, and of course the three churches are within a 5 minute walk. The space is colourful and cheery with an east coast vibe. The apartment has a well equipped kitchenette if you prefer to cook light meals yourself. There is also a dining area which could be used as a very comfortable work space. Enjoy our beautiful town!

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
4.96 out of 5 average rating, 246 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
Home in Lunenburg
4.94 out of 5 average rating, 173 reviews

OceanFront #12 HotTub Private Deck waterfront BBQ

Take it easy at this unique and tranquil getaway.and a waterfront deck brimming with amenities. Enjoy the comforts of home and beyond with air-conditioning, a fire pit, and more in this private community oasis. Complete with a private pier and boat launch, HOOK'd 12 invites you to experience waterfront living at its finest, just moments away from the heart of Lunenburg village.

Popular amenities for Chester holiday rentals

When is the best time to visit Chester?

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Avg. price$195 AUD$196 AUD$184 AUD$202 AUD$209 AUD$257 AUD$292 AUD$348 AUD$264 AUD$253 AUD$202 AUD$256 AUD
Avg. temp-6°C-6°C-2°C4°C10°C14°C17°C17°C14°C9°C4°C-2°C

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Chester?

    Yes! Work meets play with ease at over 20 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Chester?

    Four-legged friends are welcome in Chester. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Do house rentals in Chester have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Chester. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chester have air conditioning?

    Absolutely! We offer over 20 house rentals with air conditioning in Chester. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in house rentals in Chester?

    Experience the best of Chester with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there family-friendly house rentals in Chester?

    Chester has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Chester have free parking?

    Absolutely! We offer over 30 house rentals with free parking in Chester. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Chester have wifi?

    Absolutely! We offer over 30 house rentals with wifi in Chester. Enjoy a tailored experience with all the comforts you desire.

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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