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House holiday rentals in Chester

Find and book unique houses on Airbnb

Top-rated house rentals in Chester

Guests agree: these houses are highly rated for location, cleanliness and more.

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Top guest favourite
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 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, 564 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, 140 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 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, 158 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 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, 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 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.

Top guest favourite
Home in Lunenburg
5 out of 5 average rating, 129 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 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, 100 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
The exterior of the architecturally unique cottage is showcased in the twilight. The structure features large windows and a sleek design, elevated on supports. Surrounded by natural landscapes, two chairs are positioned on the deck, offering a space to enjoy the views.
Home in Terence Bay
4.89 out of 5 average rating, 240 reviews

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.

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
4.95 out of 5 average rating, 243 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.

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 770 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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