
Holiday rentals in Chester
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Top-rated holiday rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness and more.
Mahone Bay Hide-Away
Hide-Away and rejuvenate in your very own 360 sq ft luxury tourist suite just a stones throw from the shops, galleries, dining, hiking and biking that picturesque Mahone Bay has to offer. This newly-built open concept tourist suite coupled with “ Getaway by the Bay” and “Haven In The Bay”, includes all the conveniences of home making this the ideal property to pamper yourself. The Hide-Away features luxury linens, gourmet equipped kitchen, spa-like ensuite, cable, Wi-Fi internet, dishwasher, washer/dryer, barbecue ( spring, summer, fall only) and fabulous indoor and outdoor space. Affiliated with Tourism NS, Canada Select and NS Approved. Snuggle and sip wine on the couch or enjoy your favourite local beer on the wraparound deck while firing a fine cut steak on the barbeque. It is up to you, it is your vacation. The Hide-Away on the Hill is the consummate location to use as your home base as you explore Nova Scotia. Book today and experience why our guests love to rebook. All our guests have access to the entire home and outdoor space. Your hosts, Pam and David, are born and raised in the area, live close by, available 24/7, and are an excellent resource to answer any questions you may have or suggest local excursions. Situated in the heart of Mahone Bay, this home is a great starting point to explore the southern shore and other parts of Nova Scotia. Peggy's Cove, Halifax, Annapolis Valley, Gulf tidal bore, surfing, and much more are all nearby. Mahone Bay is a small ocean side walkable community with local taxi service available. This home is a brand new construction in 2018. You can be one of the first to experience the luxury and detail designed for your comfort and enjoyment. Please view our other AIRBNB listing , Getaway By The Bay

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

Studio Apt at Cove Cottage Eco Oasis
Cove Cottage is a lakefront eco-retreat tucked into the woods, 45 mins from HRM. We vibe with nature. Walk the boardwalk, sit lakeside enjoying the views, feed the chickens, wander the gardens, or currently the snow banks ❄️ We are scent free & all natural with 100% cotton bedding Your stay includes a DIY Breakfast bar: Pancakes, syrup, rolled oats & oatmeal pkgs & of course coffee and tea Studio Suite is an Apartment here in our main building, more detail ⬇ TT, IG & FB: covecottageecooasis

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

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!

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.

The Oasis on Blueberry Lane
Welcome to your private lakefront escape in Chester Grant. Swim from the dock on a warm, swimmable lake, paddle at sunrise, and soak in the hot tub beneath star-filled skies. Gather around indoor and outdoor wood fires in every season, then head inside for pool tournaments and spacious, comfortable living designed for connection and relaxation. Just 10 mins to Sensea Nordic Spa and 30 mins to Ski Martock, the perfect four-season retreat for families and friends year-round.

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.

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.

Nordic Tides Retreat Sauna & Spa
Welcome to Nordic Tides, where minimal Nordic design meets Nova Scotia’s rugged coastline. This oceanfront retreat features panoramic views, a private sauna, hot tub, and fire pit—perfect for slowing down and soaking in sea, sunrise, and stars. Unwind, reconnect with nature and loved ones, and feel restored in a space designed for balance, beauty, and intentional living.
Popular amenities for Chester holiday rentals
Stay near Chester's top sights
Other great holiday rentals in Chester

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

Home in the Heart of Chester

The Hull House: modern beauty on quiet ocean cove

The Oaks Seaside Retreat

In ground HOT TUB + 2 primary bedrooms w/ ensuites

Lake House Escape

Lake House

The Narrows Nest
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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- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Conrad's Beach
- Lawrencetown Beach Provincial Park
- Ski Martock
- Canadian Museum of Immigration at Pier 21
- Point Pleasant Park
- Halifax Public Gardens
- Maritime Museum of the Atlantic
- Halifax Central Library
- Dalhousie University
- Luckett Vineyards
- Kejimkujik National Park & National Historic Site
- Halifax Waterfront Boardwalk
- Fisherman's Cove
- Crystal Crescent Bch Provincial Pk
- Shubie Park
- Grand-Pré National Historic Site
- Museum of Natural History
- Big Mushamush Lake
- Peggys Cove Lighthouse




