
Holiday rentals in Chester
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Top-rated holiday rentals in Chester
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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

Fox Point Lake House - Luxury Lakefront Rental!
Featured on Home Shores - Season 2, Episode 1! This one of a kind luxury lake house has plenty to offer. Gorgeous lakefront, private beach, hot tub that overlooks the lake, water views from the main floor and primary bedroom, wood fireplace and the list goes on. Other features include: - 30 mins from Halifax - Cathedral ceilings with A frame front - Built in wet bar with wine and beer fridge - Private sand beach - Salt water hot tub that comfortably sits 7 Check our IG - @foxpointlakehouse

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

FFA Close to Nordic Spa — Accepting Travel Nurses
• "Occupancy Fees or Property use taxes" is the mandatory local sales tax charged by Airbnb (HST 14%) • 3pm Checkin • 15 mins from NORDIC Spa • 10 mins from Mahone Bay • Shared laundry facilities • Free bikes provided with access to the Chester Connection Trail • A/C, cable TV, wifi & free parking on site • Cozy & comfortable with a large back deck, BBQ. Stand up shower only. • Please note this cottage has 7' ceilings (not 8') • The second bedroom is best suited for a child (more info below)

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!

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.

Waterfront loft with million dollar views- Suite 1
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.

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.

Norse Geodesic Retreat (Freya)
Experience the epitome of relaxation and luxury at Norse Geodesic Retreat. Nestled amidst nature's embrace, our distinctive geodesic domes offer an unrivaled escape from the hustle and bustle of everyday life. Step into a world of elegance and tranquility as you gaze through floor-to-ceiling windows at the breathtaking views outside. Unwind on your private deck, where a rejuvenating soak in the hot tub awaits under the starlit sky.

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.

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.

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
Stay near Chester's top sights
Other great holiday rentals in Chester

Lakefront Luxury Retreat

Fox Creek Cottage | Fox Point Lake | Hot Tub/Kayak

Half Moon Cove Retreat

Steel the Wave

Cozy Chester cottage on the Water.

One 12 Queen - EV Charger

In ground HOT TUB + 2 primary bedrooms w/ ensuites

Blysteiner Lake Dome
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $177 SGD | $178 SGD | $167 SGD | $184 SGD | $190 SGD | $234 SGD | $266 SGD | $316 SGD | $240 SGD | $230 SGD | $184 SGD | $232 SGD |
| Avg. temp | -6°C | -6°C | -2°C | 4°C | 10°C | 14°C | 17°C | 17°C | 14°C | 9°C | 4°C | -2°C |
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 holiday rentals in Chester

Total holiday rentals
Explore 50 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at $64 SGD 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 & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
50 of Chester holiday 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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