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House holiday rentals in Chester

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Top-rated house rentals in Chester

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Guest favourite
A spacious living area features a large sectional sofa adorned with patterned cushions and a rustic coffee table. Two pieces of colorful artwork hang on the wall, complemented by decorative items on the table. The dining table can be seen in the background, surrounded by wooden chairs.
Home in Hubbards
4.95 out of 5 average rating, 144 reviews

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.

Top guest favourite
A charming tiny home is set amidst a lush landscape, with green foliage and rocks surrounding its base. The deck extends outward, featuring large windows that invite natural light. The gentle pathway meanders around the property, bordered by vibrant greenery and trees.
Home in Crousetown
4.98 out of 5 average rating, 565 reviews

Cozy Riverside Cottage Indoor & Outdoor Fireplace

River music awaits you. Escape the hustle and bustle of city life to embrace tranquility of nature nestled in a tiny home on 2 acres overlooking a set of rapids. Stroll along the paths and unwind or cozy up by the fire with a good book. All this awaits you at Herons Rest. This is not just a home; it's a lifestyle! If you feel like venturing out, enjoy the beauty and fun offered by the South Shore, explore its abundant beaches, restaurants, shopping and music there is something for everyone!

Guest favourite
A bright living area features a comfortable arrangement of light-colored sofas around a stylish coffee table. A white stone fireplace stands as a focal point, while natural light floods in through large windows. Wooden beams add character to the high ceiling.
Home in Hubbards
4.93 out of 5 average rating, 141 reviews

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!

Top guest favourite
A charming, historic house is nestled on a hill, surrounded by vibrant flowers and greenery. The exterior showcases a blend of gray shingles and natural wood, with inviting porches that enhance its appeal. The sky above is bright with scattered clouds, adding to the home's radiant character.
Home in Hubbards
4.96 out of 5 average rating, 216 reviews

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.

Top guest favourite
The serene lake is bordered by trees and reflects a clear blue sky. A dock with two blue chairs extends into the water, and a floating device is visible nearby. The calm surface of the lake enhances the peaceful ambiance.
Home in Chester Basin
4.96 out of 5 average rating, 159 reviews

The Oasis on Blueberry Lane

Enjoy swimming or kayaking in our beautiful lake. Afterwards, hop in the hot tub to relax your tired muscles, then roast marshmallows over the firepit or have a game of pool. You can also curl up next to wood stove for a lazy evening in. Take a short drive to one of the several stunning beaches. Enjoy being 10 minutes from both SENSEA Nordic Spa, and Chester Village - where you'll find Chester Golf Course, a selection of restaurants, cafes, and shops. Only 30 minutes to ski Martock!

Top guest favourite
An aerial view of the oceanfront property alongside a rocky shoreline reveals a spacious lawn and several nearby homes. The scene includes vibrant green grass and red outdoor chairs positioned near the water, complemented by the dramatic coastal landscape of Peggy's Cove.
Home in Peggy's Cove
4.89 out of 5 average rating, 144 reviews

Peggy's Cove - Modern Home with Lighthouse View

Forget your worries in our spacious and serene oceanfront 3 bedroom home with stunning views of Peggy's Cove and the ocean! Our beautiful home can sleep up to 7 guests comfortably and includes many features such as a BBQ, fire table, outdoor deck with views of the ocean, & seating right near the water. We are a short walk to Peggy's Point, Peggy's Point Lighthouse, & many other places on the cove like shops, restaurants, hiking trails & nature parks. Enjoy your stay!

Guest favourite
Home in Mahone Bay
4.97 out of 5 average rating, 217 reviews

Mahone Bay Ocean Retreat

Your luxury ocean getaway and private spa for two. Private beach access, keyless self check-in. On the beautiful South Shore minutes from town. Cathedral ceilings & epic views. Four seasons. Hot-tub, full spectrum infrared sauna, both indoor & outdoor rainfall showers. Indoor wet room with claw foot tub. Bbq, wireless wifi, chef’s kitchen, wine fridge, AC, wood stove, Netflix, and King size bed with premium linens. A calm, luxurious space flooded with natural light.

Superhost
A close-up view of a vintage brass doorknob is featured, leading into a well-lit bedroom. The soft white bedding is neatly arranged on the spacious bed, with a dark accent pillow enhancing the serene atmosphere. A small plant sits beside the bed, adding a touch of greenery.
Home in Mahone Bay
4.91 out of 5 average rating, 135 reviews

Welcome to the Cozy Quilt

Welcome to the Cozy Quilt! A focal point of the Main Street and located in the heart of Mahone Bay. It’s sits across from the government wharf where you are only a short stroll to the cafes, brewery, pub, restaurants and shops. What started as part of the general store in 1867, the residence was later removed from the store and moved to its current home at 664 Main Street. Since 2003 it has been home to the Quilt Shop which help inspired the name Cozy Quilt.

Top guest favourite
Two kayakers navigate the calm waters of Fox Point Lake, framed by a lush green landscape. In the background, a charming log cottage with a dark roof is visible, surrounded by several outdoor seating options and colorful furnishings.
Home in Hubbards
4.95 out of 5 average rating, 103 reviews

Lakeview Cottage | Fox Point Lake | Hot tub/Kayaks

Welcome to our charming Lakeview cottage on Fox Point Lake in Hubbards, NS! This rustic log home boasts 3 bedrooms and 1.5 baths, making it perfect for families or friends seeking a peaceful retreat. Enjoy our private dock on the lake and take advantage of kayaks for fun-filled water adventures (seasonal). Unwind, reconnect with nature, and create cherished memories. Book now for an unforgettable lakeside getaway!

Top guest favourite
A large dining area features a wooden table surrounded by black chairs, set against expansive windows overlooking the water. Sunlight floods the room, highlighting the serene view of the lake and distant shoreline.
Home in Mahone Bay
4.96 out of 5 average rating, 246 reviews

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.

Top guest favourite
Home in Lunenburg
4.94 out of 5 average rating, 169 reviews

OceanFront #12 HotTub Private Deck waterfront BBQ

Take it easy at this unique and tranquil getaway.and a waterfront deck brimming with amenities. Enjoy the comforts of home and beyond with air-conditioning, a fire pit, and more in this private community oasis. Complete with a private pier and boat launch, HOOK'd 12 invites you to experience waterfront living at its finest, just moments away from the heart of Lunenburg village.

Top guest favourite
A modern living area is highlighted by a spacious sectional sofa adorned with decorative cushions. A stylish chandelier hangs above, while natural light floods in from large windows. A small side table is nestled beside the sofa, contributing to the inviting layout.
Home in Lunenburg
4.97 out of 5 average rating, 136 reviews

Conrad House - A Lunenburg Waterfront Retreat!

Welcome to the Conrad House - Your charming waterfront retreat in beautiful Lunenburg, Nova Scotia! Our 3-bedroom, 2-bathroom property offers a serene escape with breathtaking water views, a BBQ, and a lovely yard. Whether you're seeking a peaceful getaway or a base to explore the stunning surroundings, our home is the perfect choice.

Popular amenities for house rentals in Chester

Quick stats about house rentals in Chester

  • Total holiday rentals

    Explore 30 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 820 verified reviews to help you choose

  • Family-friendly holiday rentals

    30 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    30 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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