House vacation rentals in Chester

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Top-rated house rentals in Chester

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Guest favorite
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 favorite
A cottage-style exterior displays a gray wood facade with white trim. A spacious deck features two white Adirondack chairs and a small table, surrounded by greenery. Red flowers in a planter add a pop of color, while a barbecue is placed in the corner.
Home in Mahone Bay
4.97 out of 5 average rating, 192 reviews

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

Top guest favorite
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, 563 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 favorite
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, 138 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!

Guest favorite
Home in Chester Basin
4.93 out of 5 average rating, 194 reviews

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.

Top guest favorite
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 favorite
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, 158 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 favorite
An open living area features wooden beams above, enhancing the spacious feel. Grey chairs surround a light wood table, with a white writing desk positioned nearby. Stainless steel appliances are visible in the kitchen, and large windows allow natural light to fill the space.
Home in Greenfield
4.98 out of 5 average rating, 156 reviews

Lakefront home with hot tub

Unwind at Hidden Lake West, your peaceful haven on Nova Scotia’s stunning south shore. Embrace the serene beauty with exclusive lake access, where you can paddleboard, canoe, or simply relax by the water. Soak in the rejuvenating hot tub, surrounded by nature’s embrace. This cozy with modern comfort, offering the perfect blend for a memorable escape. Whether you're seeking adventure or a restful retreat, Hidden Lake West invites you to relax and recharge in a breathtaking setting.

Top guest favorite
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, 141 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 favorite
Home in Mahone Bay
4.97 out of 5 average rating, 215 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.

Top guest favorite
Home in Lunenburg
5 out of 5 average rating, 128 reviews

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.

Top guest favorite
A spacious dining area features a long wooden table surrounded by white chairs, with large windows offering panoramic ocean views. Natural light fills the room, enhancing the clean lines and modern design. The serene outdoor landscape is visible through sliding glass doors.
Home in Port Medway
5 out of 5 average rating, 107 reviews

the Escape - A Private Oceanfront Getaway

The ESCAPE provides a private oceanfront retreat for you and your family or friends to enjoy. Modern newly built house on large private oceanfront lot. Enjoy the endless ocean views from the large oversized deck, relaxing hot tub, large lawn or oceanfront fire pit. Explore the rocky shoreline and beach areas from your front steps! This remarkable getaway is located less than 1.5hrs from Halifax and is a short drive off the highway.

Popular amenities for Chester house rentals

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$10,468 GYD per night before taxes and fees

  • Verified guest reviews

    Over 770 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 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!

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