
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.

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!

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.

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.

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.

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.

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.

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.

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!

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

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.

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.

Nordic Tides Retreat Sauna & Spa
Welcome to Nordic Tides, where minimalist Nordic design meets Nova Scotia’s rugged coastline. This oceanfront retreat offers panoramic views, a private cedar sauna, hot tub, and fire pit. Perfect for slowing down, soaking in the sea, sunrise, and stars, and reconnecting with nature and loved ones. Every detail is designed to create balance, beauty, and intentional living.
Popular amenities for house rentals in Chester
House rentals with a pool

White Point Resort - Panoramic Ocean View

Half Moon Cove Retreat

All Decked Out in Mahone Bay

Luxurious Home with Indoor Pool

North End Nest

Beautiful new 6 bedroom lakehouse close to Halifax

A cozy getaway for every season!

Seacliff - Luxury Waterfront Paradise - Pool & Spa
Weekly house rentals

The Little Bird Cottage

Home in the Heart of Chester

Luxury Oceanfront Cottage-Rose Bay, Lunenburg #2

Steel the Wave

The Hull House: modern beauty on quiet ocean cove

Windrose Cottage welcomes you

Fire & Stone Oceanfront Retreat

Beach Front Estate, Cleaveland Beach 72
Private house rentals

Private Oceanfront Escape

Zen Oceanfront Chalet- Hot Tub & Sauna

The old cape

Mill Lake Paradise Cottage

The Garden by the Sea

The Tidal Fox Retreat-Oceanside Air BnB

Lakefront Cottage near Peggy's Cove

Oak Island House - facing the famous island
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 $64Â 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!
Destinations to explore
- Halifax Holiday rentals
- Mid-Coast, Maine Holiday rentals
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- Cape Breton Island Holiday rentals
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- Charlottetown Holiday rentals
- Lunenburg County Holiday rentals
- Fredericton Holiday rentals
- Saint John Holiday rentals
- Dartmouth Holiday rentals
- Kennebec River Holiday rentals
- Rentals with a fireplace Chester
- Cottage rentals Chester
- Pet-friendly rentals Chester
- Rentals with beach access Chester
- Rentals with outdoor seating Chester
- Rentals with a washing machine and dryer Chester
- Family-friendly rentals Chester
- Rentals with a patio Chester
- Cabin rentals Chester
- House rentals Nova Scotia
- House rentals Canada
- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Conrad's Beach
- Ski Martock
- Lawrencetown Beach Provincial Park
- Canadian Museum of Immigration at Pier 21
- Point Pleasant Park
- Halifax Public Gardens
- Maritime Museum of the Atlantic
- Halifax Central Library
- Dalhousie University
- Halifax Waterfront Boardwalk
- Luckett Vineyards
- Crystal Crescent Bch Provincial Pk
- Fisherman's Cove
- Peggys Cove Lighthouse
- Alderney Landing
- Grand-Pré National Historic Site
- Long Lake Provincial Park
- Shubie Park
- Kejimkujik National Park & National Historic Site




