House holiday rentals in Chester

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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, 194 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 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, 164 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 favourite
Home in Chester Basin
4.94 out of 5 average rating, 200 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 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.

Guest favourite
A dining table is set with plates and wine glasses on a deck overlooking the ocean. A bouquet of vibrant flowers in a clear vase adds a colorful touch, complementing the serene view of the water and trees in the background as the sun sets.
Home in Indian Harbour
4.95 out of 5 average rating, 155 reviews

Oceanfront Guest House near Peggy's Cove

This 1680 sq ft guesthouse has its own private path to the oceanfront, a 2nd storey deck with panoramic views of Indian Harbour. It is situated 4 kms from Peggy's Cove, and is within an hour of Halifax and Lunenburg. The property is surrounded by trees, and the only sounds are from the waves and the wind. Hiking trails are located at Polly's Cove & Peggy's Cove, sandy beaches are just a 5-40 min drive, and Oceanstone Spa Resort is a 5 min walk. It is ideally suited for stays up to 3 weeks.

Top Guest favourite
Home in Chester Basin
4.96 out of 5 average rating, 164 reviews

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.

Top Guest favourite
Home in Lunenburg
5 out of 5 average rating, 168 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
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, 121 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.

Guest favourite
Home in Lunenburg
4.82 out of 5 average rating, 106 reviews

Oceanfront Escape + Hot Tub | Near Lunenburg

✨ Highlights • Private oceanfront deck with panoramic views • Outdoor hot tub perfect for sunset or stargazing • Pet-friendly stay • Fast Wi-Fi + Smart TV for cozy nights in • Minutes from the UNESCO town of Lunenburg • Peaceful coastal setting 🌊 Oceanfront Retreat with Hot Tub & Sunrise Views Relax, recharge, and wake up to the sound of the ocean. Deck view of Nova Scotia’s breathtaking coastline. PARKING: Space for 1

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
4.96 out of 5 average rating, 114 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!

Guest favourite
Home in Kingsburg
4.96 out of 5 average rating, 124 reviews

The Beach Barn + Cedar Sauna

The Beach Barn is 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

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, 264 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.

Popular amenities for Chester house rentals

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 $101 NZD per night before taxes and fees

  • Verified guest reviews

    Over 860 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Chester holiday 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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