Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite
Villa in Chester
4.93 out of 5 average rating, 150 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 favorite
A spacious living area features large windows providing ample natural light and views of greenery and colorful buildings across the water. A comfortable sofa is positioned next to a white coffee table, which holds decorative plants, while a dining set is discernible in the background.
Guest suite in Lunenburg
4.97 out of 5 average rating, 656 reviews

Lunenburg Harbourfront Hideaway-The View-Sauna!!**

The fully updated suite, boasts breathtaking, panoramic harbour views, sprawl out on the king-size bed and let your dreams set sail. Enjoy front row waterfrontage, boats sailing by, horses trotting along the iconic Bluenose Drive. This 19th century building offers the perks of a boutique hotel; infrared sauna, bathrobes, LED TV, iron, hairdryer, Keurig, microwave, mini fridge, with its own private entrance. Located 50m from the Bluenose, you can not get any closer, without staying onboard!

Guest favorite
Shipping container in Chester
4.97 out of 5 average rating, 86 reviews

Tiny Home, Shipping Container, Chester NS, Canada

Escape to The Hemlock Hideaway — A Modern Shipping Container Retreat Tucked away in Chester NS, this sleek and stylish tiny home offers big comfort in a compact space. Featuring a cozy interior, outdoor seating, and all the essentials for a peaceful getaway. Unplug, unwind and experience container living like never before. ☆ Brand New Shipping Container 320 sqft tucked away in Chester NS. Nordic spa, Ski Martock, golf ☆ Hot tub ☆ Fully equipped Kitchen, Tea and coffee ☆ Wifi ☆ Large TV

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

Guest favorite
An open-concept living space is presented, featuring a sleek kitchen area with wooden cabinetry and modern appliances. A spacious granite island with seating for six complements leather swivel chairs and a white leather sofa. Large glass doors lead to a small balcony, enhancing natural light.
Condo in Chester
4.97 out of 5 average rating, 74 reviews

Captain's Quarters - 2 bedroom harbourview condo

Located in the heart of sea-side Chester, Nova Scotia with a gorgeous, full view of the front harbour. The Captain’s Quarters is a bright and beautifully finished, spacious, 2-bedroom condo that is central to all that scenic Chester has to offer. Walking distance to the pubs, restaurants, bakery, yacht club & much more! Large, floor-to-ceiling windows offer a perfect view of Mahone Bay. Less than a 5-minute drive to Sensea Nordic Spa - a perfect home base for your South Shore stay.

Top guest favorite
Apartment in Mahone Bay
4.97 out of 5 average rating, 106 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 favorite
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 favorite
A hot tub sits on a wooden deck, offering a view of the calm water reflecting the overcast sky. The sleek black structure in the background contrasts with the serene landscape, creating an inviting space for relaxation.
Chalet in Lunenburg
4.89 out of 5 average rating, 295 reviews

Waterfront Honeymoon Loft

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 favorite
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.

Top guest favorite
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, 256 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 favorite
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, 117 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.

Top guest favorite
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!

Popular amenities for Chester vacation rentals

When is the best time to visit Chester?

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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 vacation rentals in Chester

  • Total vacation rentals

    Explore 40 vacation rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at € 51 per night before taxes and fees

  • Verified guest reviews

    Over 1,660 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Chester vacation 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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