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
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
A hand-built wood-fired hot tub is nestled among trees, surrounded by wooden decking. Sunlight filters through the forest canopy, creating an inviting atmosphere. A metal bucket rests nearby, adding a rustic touch to the serene outdoor space.
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
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 bright living area features high ceilings with wooden beams and a large window wall that offers a clear view of Scotch Cove. Natural light floods the space, highlighting a comfortable sofa and a cozy chair, creating an inviting environment for relaxation.
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
A spacious wooden deck overlooks a tranquil lake, surrounded by lush greenery. A sun lounger is positioned beside a large umbrella, providing shade. The deck is enhanced by sturdy railings, inviting relaxation amidst the natural setting.
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 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 bright and airy living space features large windows offering scenic views of the water. A modern kitchen island equipped with stools overlooks a cozy seating area with a comfortable sofa and tasteful decor. Soft natural light enhances the inviting ambiance.
Home in Lunenburg
5 out of 5 average rating, 142 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.

Top Guest favourite
A comfortable living room is presented, featuring a neutral-colored sofa and armchair set adorned with colorful patterns. A coffee table sits in the center, surrounded by a textured area rug. Light enters through multiple windows, enhancing the space's inviting feel and a potted plant is placed nearby.
Guest suite in Lunenburg
4.97 out of 5 average rating, 374 reviews

A Suite Stay!

Whether you are looking for a weekend get away or have business in the local area, we have the perfect place for you. Just 3 minutes from Mahone Bay, 7 from Lunenburg and 25 minutes from Sensea Nordic Spa in Chester. Enjoy the convenience of a full kitchen, relaxing living room, spacious bedroom and bathroom! Enjoy an outdoor fire pit after a day of exploring! Meet our greeters, Max & Ruby. They love to see everyone!!

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, 134 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
Guesthouse in Chester Basin
4.86 out of 5 average rating, 152 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

When is the best time to visit Chester?

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Avg. price$231 NZD$233 NZD$218 NZD$240 NZD$248 NZD$305 NZD$347 NZD$412 NZD$313 NZD$300 NZD$240 NZD$303 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 $84 NZD 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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