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$12,557 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.

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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, 166 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
4.94 out of 5 average rating, 201 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, 217 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
Home in Lunenburg
4.97 out of 5 average rating, 143 reviews

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!

Top guest favorite
Home in Chester Basin
4.96 out of 5 average rating, 166 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.

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, 155 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!

Top guest favorite
An overhead view captures a private hot tub filled with clear water beside a modern fire pit, surrounded by wooden decking. The gentle bubbling of the hot tub water contrasts with the flickering flames of the fire, creating a serene outdoor relaxation area.
Home in Riverport
4.96 out of 5 average rating, 339 reviews

Orig.Inns - The Barn Retreat & Hot Tub

Welcome to The Barn — a cozy hilltop escape overlooking Ritcey Cove in Riverport. This small home offers a peaceful setting surrounded by nature, where you can truly slow down and relax. Enjoy quiet mornings with a view, and restful evenings with nothing but the sounds of the outdoors. Just minutes away, you’ll find beautiful beaches and scenic hiking trails to explore. Comfortable, calm, and easy — the kind of place you’ll want to return to. Follow us @Orig.Inns

Guest favorite
Home in Terence Bay
4.91 out of 5 average rating, 121 reviews

Back Bay A-Frame

Relax at this unique and tranquil getaway. A short 20 minute drive from Halifax, this fully equipped home will allow you to relax and recharge. The indoor fireplace will provide a relaxing ambiance. The spacious spa like bathroom will allow you to pamper yourself throughout your visit. Close to the ocean, local beaches, nature trails and boutique restaurants, you will feel connected to the Nova Scotian charm while remaining only a few minutes drive from the city.

Top guest favorite
Home in Kentville
4.98 out of 5 average rating, 433 reviews

Hot Tub Retreat | Valley Views | Near Kentville AC

Welcome to “The Twelve,” a luxury 2-bedroom retreat set privately in the Annapolis Valley, just 15 minutes from Wolfville. Perfectly located for exploring the region’s wineries and craft breweries, this stylish home offers a relaxing and elevated getaway. Step into a bright, open-concept space with a modern kitchen and peaceful valley views. Unwind in the private hot tub with your favourite wine, or take in beautiful sunrises and sunsets from the deck.

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, 124 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.

Top guest favorite
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, 115 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 favorite
The exterior of a modern home is shown at dusk, with a vibrant sunset illuminating the sky in shades of pink and orange. A spacious deck extends from the house, featuring seating arrangements for relaxation, while a field of wildflowers occupies the foreground.
Home in LaHave
4.97 out of 5 average rating, 106 reviews

The Lookout - Cottage

Luxury modern home with incredible ocean views. Just under 1,000 sq. ft. on 2 acres of land, The Lookout has been meticulously designed with a chef's kitchen, gas fireplace, heated bathroom floor, SmartTV, Wifi and some of the best views on the South Shore. The Lookout is ideal for a family, couple's getaway, girls weekend and anyone wanting to explore the natural beauty of Nova Scotia. We also welcome pets!

Popular amenities for Chester house rentals

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