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Vacation rentals in Chester

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Top-rated vacation 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 homes in Lunenburg
4.97 out of 5 average rating, 369 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, 133 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 spacious deck is visible, featuring a hot tub and comfortable seating arrangements. The area is designed for relaxation and entertainment, bordered by a glass railing that offers unobstructed views of the tranquil water and surrounding landscape.
Bungalow in Lunenburg
5 out of 5 average rating, 124 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 homes in Nova Scotia
4.97 out of 5 average rating, 239 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

Guest favourite
The kitchen showcases a modern design with natural wood finishes and exposed beams. Equipped with stainless steel appliances, it features a spacious countertop beside two bar stools. Large windows allow ample natural light, highlighting the warm tones of the wood throughout the open-concept space.
Cabin in LaHave
4.97 out of 5 average rating, 849 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, 104 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, 264 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

Top guest favourite
A spacious bedroom features large windows allowing natural light to fill the room. A comfortable bed is centered, with a modern fan above. A foosball table adds recreational space, while a closet and additional storage are present, accentuated by soft-colored walls and tasteful furnishings.
Apartment in Mahone Bay
4.97 out of 5 average rating, 103 reviews

Guest accomodation in Mahone Bay town

Beautiful suite in quiet, central area of Mahone Bay. Steps to main street but away from the traffic and backing onto the park. The suite is one wing of a large, older historic home. The property is in the heart of one of the South Shore's most picturesque seaside towns. The property is about 1 hour from Halifax and the airport and is walkable to many restaurants, stores, the harbor, and trails. The children's park is steps away, as is the town swimming pool.

Top guest favourite
Home in Mahone Bay
4.97 out of 5 average rating, 208 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.

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, 377 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
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
4.96 out of 5 average rating, 369 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, 118 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 vacation rentals

When is the best time to visit Chester?

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Avg. price$192 CAD$194 CAD$181 CAD$199 CAD$206 CAD$254 CAD$301 CAD$344 CAD$257 CAD$252 CAD$198 CAD$195 CAD
Avg. temp-6 °C-6 °C-2 °C4 °C10 °C14 °C17 °C17 °C14 °C9 °C4 °C-2 °C

Quick stats about vacation rentals in Chester

  • Total vacation rentals

    Explore 50 vacation rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at $70 CAD per night before taxes and fees

  • Verified guest reviews

    Over 1,490 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Chester vacation 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!

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