
House vacation rentals in Chester
Find and book unique houses on Airbnb
Quick stats about house rentals in Chester

Total vacation rentals
Explore 30 vacation rentals in Chester

Nightly prices starting at
Chester vacation rentals start at G$12,546 GYD per night before taxes and fees

Verified guest reviews
Over 860 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 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!
Top-rated house rentals in Chester
Guests agree: these houses are highly rated for location, cleanliness, and more.

Salt & Tide Ocean Retreat
The eat in kitchen includes a large stainless steel fridge and full size stove. We have a good collection of spices and cooking supplies in the pantry for making cookies with the kids. Walk out to the back deck to bar-b-que or watch the kids play in the oversized 1 acre lot. The dining room comfortably seats six for family dinners to share the stories and adventures of the day. Views of the ocean from both the dining room and adjoining family room with bright south western facing windows lets you take in the amazing sunsets. A cozy den with wood burning fireplace is great if you are visiting in the Winter/Fall months. A nice spot to sit and relax and write in your journal after a busy day touring the South Shore. The main floor bathroom also has a large modern shower. Washer and Dryer are also located on the main floor and this house has a clothes line in the back. Where possible our housekeeper hangs the sheets out on the back line to blow dry for you to enjoy "fresh" clean bedding. Upstairs are four bedrooms perfect for the entire family or convenient if there are two smaller families travelling together. The upstairs contains a full bathroom that has double sinks to make getting the gang ready for the day move a bit quicker. The master bedroom has an ensuite bathroom. The two front bedrooms have ocean views and you can listen to the waves at night for a relaxing sleep. The beach in front (end of driveway and across the road) is flat pebble beach stones which is great for walking on, wading out into Shoal Cove and makes an amazing spot for bon-fires on the beach as you enjoy the sunsets and brilliant starry night sky. The water frontage showcases the two Tancook islands and across the Mahone Bay sits Chester and the infamous Oak Island (aka treasure island). Located on the Aspotogan Coastal Drive (Hwy NS-329) where the famous Bayswater Beach and provincial park is only 5 mins away. The local convenience store and "The Deck" restaurant are a one minute walk. Great for dropping in for a seafood chowder & pie or to get your daily ice cream fix in the afternoon. There is lots to do in the South Shore in case you are new to the area. Charter a sailboat, kayak or fishing boat to enjoy the area from the water. The Aspotogan Coastal Drive is heaven for bikers as much of the route is ocean side and in the summer it is common to see lines of 20-30 bikers peddling past our place. Hop on the Tancook Ferry and drive around the islands to explore the multi-colored homes. A short 20 minute drive will get you to either Chester or Hubbards. Make sure you visit the Hubbards farmers market on Saturday mornings in the spring/summer. Chester is famous for sailing and hosts the Chester Race week August 15-18th 2018. Visit Lunenburg (45 mins away) and tour shops, restaurants and the shipyards that built the famous Nova Scotia flagship BlueNose II. Take a day and tour the many vineyards and wineries located through-out the Annapolis valley (50 mins drive). And if you want to spend time in the big city, Halifax is only 45 minutes away. Our goal is to provide you and your family with a great experience so our vacation home has more to offer than just a place to sleep. Properly equipped with the amenities you require. Note: For groups over 4 guests there is an additional cleaning fee of $15 per person. Entire property, main and upper levels of house are available. Basement is not fimished so not part of rental. Andrew is reachable by text, e-mail or phone call to answer questions, provide recommendations, or make sailing arrangements, if available, to take you sailing out of Halifax on our 30 foot sloop. (moderate captain's fee applies). Opposite the beach in Shoal Cove, the house looks across the Mahone Bay and two Tancook islands. A local store and restaurant are a minute’s walk away. Bike the oceanfront, charter a boat, or hop on the Tancook Ferry and drive around the islands. Vehicle is required. Premium support when you need it When you book an Airbnb Plus home, you get the focused attention of our Airbnb Pluscustomer support team–a highly-trained team committed to great service and faster responses.
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Millet Lake House • Hot Tub • Sandy Beach
"Like having your own private resort" - Millet Lake House is welcoming, warm & every little comfort has been considered. Serious staycations start & end right here. Perfectly perched on peaceful forested acreage overlooking over 250ft of your own sandy beachfront, the setting is simply unmatched. Privacy, finishes, the outdoor toys & all of the special little touches to ensure everyone's vacation goals are exceeded. The reviews & the reputation as the South Shore's premium lake front retreat.
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Hubbards Cozy Convenient Cottage
Welcome to our cozy cottage located in the centre of Hubbards - just steps away from all of the fabulous amenities the area has to offer. Our home has been fully updated with you in mind. We've aimed to provide comfort, cleanliness, and loads of charm! The space accommodates six in three bedrooms and one and a half baths. Ideally situated with restaurants, cafes, grocery, liquor and an amazing farmers market just across the street! You've found the ultimate home base for a South Shore adventure!
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The Creation Lounge Retreat - A Unique Gem!
Step into this fully renovated, open-concept mid-century modern character home, where you're embraced by soaring 16' ceilings, serene water views, and a peaceful atmosphere that immediately puts you at ease. Large hot tub with water views. Pedal Boat, swimming lake nearby, fire pit, board & lawn games, host arts/crafts 4 sale. Just 25 min to DT Halifax or Peggy's Cove. Food, liquor, drug stores etc. only 5-10 min. away! As featured in TV series; Home Shores - Ssn 7 Registration: STR2425A6031
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Ocean Front #2 HotTub 2 bdrm Rooftopdeck BBQ 2bath
Escape to Oceanfront Bliss! This stunning property features an epic deck, perfect for sunbathing or evening gatherings. Step inside to discover modern finishes a blend style & comfort soak in a hot tub with ocean views. Rooftop deck for stargazing& Sunsets! The luxurious King Master suite with an ensuite and a cozy queen bedroom provide ample space for family and friends. Experience the ultimate lifestyle of relaxation, where every moment is a celebration, create memories. Book your stay now!
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Gorgeous Oceanfront Estate in Peggy’s Cove
Enjoy one of the most unique private oceanfront properties in southern Nova Scotia! A newly furnished year-round home with all the amenities, 1,000ft of oceanfront with beautiful docks, a sand-pebble beach and stunning sunsets! At night, enjoy the sky full of stars and sounds of the ocean around the large fire-pit, and in the morning watch the sunrise over the crystal clear lake in front of the home. Room for family and friends, located within minutes of Peggy’s Cove and 25 min from Halifax.
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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.
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Nordic Tides Retreat Sauna & Spa
Welcome to Nordic Tides, a private oceanfront home on Nova Scotia’s rugged coastline with wide Atlantic views, warm modern design, and space to gather with family and friends. The home includes a cedar sauna, outdoor hot tub, fire pit, BBQ, billiards table, and generous indoor and outdoor areas. It is ideal for guests looking for a quiet coastal escape, time together, and a comfortable place to relax after exploring Hubbards and the surrounding beaches.
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Oceanfront | Hot Tubs | Sauna | Gym | Game Rooms
Escape to our stunning oceanfront property next to Fox Point Beach in Hubbards, NS! This listing includes both Seashore & Shoreside units: 5 bedrooms, 3 bathrooms, 2 kitchens, and 2 private saltwater hot tubs. Enjoy a 75” smart TV, home theater seating, arcades, ping-pong, air hockey & more. Plus, access a full gym & infrared sauna in a separate building. Perfect for families & groups looking for relaxation, fun, and breathtaking views!
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The Beach Barn + Cedar Sauna
The Beach Barn and Cedar Sauna are located atop the highest hill in lower Kingsburg with breathtaking views overlooking Hirtle's Beach best known for its surf. This 2 bed, 2 bath award-winning home designed by renowned architect Brian MacKay-Lyons incorporates 30-foot high vaulted ceilings and open concept design. A quick 10-minute walk to Hirtles Beach, your coastal escape awaits! Check us out on IG @kingsburgcabins
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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.
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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!
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Popular amenities for Chester house rentals
House rentals with a pool

Beautiful new 6 bedroom lakehouse close to Halifax
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North End Nest
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Land Yacht Oceanfront Luxury + Indoor Pool Escape
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Half Moon Cove Retreat
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Bayswater Beach Retreat - 4 bdrm w/ hot tub
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Oceanview Luxury Estate - Magazine Perfect!
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All Decked Out in Mahone Bay
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The Backyard Brook Bungalow STR2627A5027
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Weekly house rentals

The Lookout - Cottage
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Luxury Getaway Home | Cozy Vacation in Mahone Bay
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The Whale House
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Storybook coastal farmhouse with ocean access
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White Cottage
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Home in the Heart of Chester
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Beautiful home in picturesque Chester NS
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One 12 Queen - EV Charger
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Private house rentals

The Tidal Fox Retreat-Oceanside Air BnB
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Stillshore | Luxury Lakehouse Retreat | Hot Tub
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Windrose Cottage welcomes you
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Cozy Cottage by the River
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Lake House
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Coastal Gale, Hot Tub, Ocean View, Blue Rocks
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Seaside Stay
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The Little Bird Cottage
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Destinations to explore
- Halifax Vacation rentals
- Bar Harbor Vacation rentals
- Moncton Vacation rentals
- Charlottetown Vacation rentals
- Fredericton Vacation rentals
- Saint John Vacation rentals
- Bangor Vacation rentals
- Ellsworth Vacation rentals
- Dartmouth Vacation rentals
- Cape Breton Island Vacation rentals
- Gaspé Vacation rentals
- Dieppe Vacation rentals
- Rissers Beach Provincial Park
- Oak Island
- Kejimkujik National Park & National Historic Site
- Hirtle's Beach
- Lawrencetown Beach Provincial Park
- Dalhousie University
- Halifax Citadel National Historic Site
- Conrad's Beach
- Big Mushamush Lake
- Long Lake Provincial Park
- Shubie Park
- Rainbow Haven Beach
- Point Pleasant Park
- Maritime Museum of the Atlantic
- Halifax Public Gardens
- Luckett Vineyards
- Crystal Crescent Bch Provincial Pk
- Canadian Museum of Immigration at Pier 21
- Ski Martock
- Halifax Central Library
- Halifax Seaport Farmers' Market
- Fisherman's Cove
- Sir Sandford Fleming Park
- Queensland Beach Provincial Park





