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, 385 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

Top 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, 139 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
Bungalow in Lunenburg
4.99 out of 5 average rating, 150 reviews

Ocean Front #4 Hot Tub 2bdrm huge deck BBQ 2bath

- Oceanfront, Pier, Boat Launch, - Massive Deck: Ideal for lounging entertaining, dining, High-Top Table, BBQ, Firewall: Ensures safety and peace of mind. - Hot Tub: Unwind and enjoy the serene ocean views. - Kitchen: induction cooktop and wall oven, ideal for preparing gourmet meals. - Two Bedrooms, Two Baths: The home includes a spacious master bedroom with a king-size bed and an en suite bath. - Second Bathroom: tub for a relaxing soak. HOOKd 4 perfect retreat best of oceanfront living.

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, 241 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, 866 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, 109 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
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, 274 reviews

Studio Suite Apt at Cove Cottage Eco Oasis

We're a lakefront eco-retreat tucked into the woods, 45 mins from HRM. Walk the boardwalk, sit lakeside enjoying the views or enjoy the ducks & chickens. Star-watching is a must! Your stay includes a DIY Breakfast bar: Buttermilk pancakes, syrup, rolled oats & oatmeal pkgs & of course coffee and tea. We are scent free and all natural with 100% cotton bedding! Studio Suite is an Apartment here in our main building, more detail ⬇ Find us on TT, IG & FB: covecottageecooasis

Guest favourite
Home in Mahone Bay
4.97 out of 5 average rating, 217 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, 118 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.

Guest favourite
Two modern loft-style units are positioned at the water's edge, featuring black metal siding and sloped roofs. Large windows and skylights reflect the evening light, while a box of smooth stones lines the shoreline, providing a natural transition from the building to the gentle waves.
Chalet in Lunenburg
4.91 out of 5 average rating, 386 reviews

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.

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, 240 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
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
4.93 out of 5 average rating, 58 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!

Popular amenities for Chester holiday rentals

When is the best time to visit Chester?

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Avg. price$240 NZD$242 NZD$226 NZD$248 NZD$257 NZD$316 NZD$360 NZD$427 NZD$325 NZD$315 NZD$247 NZD$243 NZD
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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 $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,490 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, Wi-Fi 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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