
Vacation rentals in Chester
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Top-rated vacation rentals in Chester
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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

Charming Ocean Retreat
Perched on a hill overlooking the Aspotogan Cove, this lovingly restored 150-year-old family home offers everything you might need for a relaxing peaceful retreat. The backyard opens onto four acres of trails - perfect for mountain biking and hiking - and Bayswater Beach, one of the exquisite beaches on the South Shore, is only five minutes away. The beautifully appointed chef’s kitchen invites culinary play, and an extensive collection of games, books and movies will keep you well entertained.

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!

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, go kayaking or swimming. We are scent free & all natural with 100% cotton bedding Your stay includes a DIY Breakfast bar: Pancakes, syrup, rolled oats & of course coffee and tea Studio Suite is an Apartment here in our main building, more detail ⬇ TT, IG & FB: covecottageecooasis

The Beach Loft: 5-bedroom
This pretty beach house is located just steps from the beautiful Seawall beach. Relax in the hot tub, hammock or next to the fire. The perfect getaway that is only 34min from Halifax. Featuring a wood burning fireplace and stone accents. Private hot tub overlooking the ocean. Post and beam Construction. Ocean views. Seawall beach is between Queensland and Cleveland’s beach. Also located on Rails to Trails path. Minutes to restaurants and coffee shops in Hubbards.

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.

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.

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!

Cozy Oceanfront Escape 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.

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.

Norse Geodesic Retreat (Balder)
Discover a summer sanctuary in our geodesic domes, where serenity meets adventure. Savor complimentary wine on your private deck amidst verdant surroundings. Dive into your private hot tub oasis or embark on a kayaking adventure on the nearby lake. Experience the perfect blend of relaxation and excitement amid nature's embrace.
Popular amenities for Chester vacation rentals
Stay near Chester's top sights
Other great vacation rentals in Chester

Witmere

Chester Basin Place

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

Stunning Mahone Bay Views

One 12 Queen - EV Charger

Chester Suite By The Ocean

The Boathouse on Scotch Cove

Sailors’ Paradise - Stevens Cove Guest Quarters
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €155 | €157 | €156 | €123 | €127 | €156 | €178 | €211 | €161 | €154 | €123 | €155 |
| 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 vacation rentals in Chester

Total vacation rentals
Explore 40 vacation rentals in Chester

Nightly prices starting at
Chester vacation rentals start at €52 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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