
House holiday rentals in Chester
Find and book unique houses on Airbnb
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 $78 SGD 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 & 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!
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.

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.

Luxury Getaway Home | Cozy Vacation in Mahone Bay
Perfect to discover Nova Scotia! Enjoy all Mahone Bay has to offer from this newly built modern home - just a small walk from the many restaurants, shops, a brewery, museums and galleries. The house has a bright open-plan living space with cathedral ceiling. The main bedroom has a queen size bed and a spotless bathroom with fresh white towels and quality toiletries. The large wraparound deck is perfect for sunny coffee mornings and soaking in the friendly atmosphere on Main Street.

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.

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

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!

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.

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, watching the sunrise over the ocean, and reconnecting with 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

Lakefront Luxury Retreat w/ Heated Pool and Arcade

White Point Resort - Panoramic Ocean View

Half Moon Cove Retreat

All Decked Out in Mahone Bay

Halifax Harbour View | Spacious Luxury + Pool

North End Nest

Beautiful new 6 bedroom lakehouse close to Halifax

Saltwater Hideaway *Wedding*Events*Content*Retreat
Weekly house rentals

Endeavour Cottage

The Whale House

Lovely oceanfront home w/4 BR + stunning views

Oceanfront Escape + Hot Tub | Near Lunenburg

White Cottage

One 12 Queen - EV Charger

The Beach Barn + Cedar Sauna

South Shore Sanctuary : Historic Church w/ Hot Tub
Private house rentals

The Little Bird Cottage

Charming Chester cottage a stone’s throw from spa

Home in the Heart of Chester

Luxury Oceanfront Cottage-Rose Bay, Lunenburg #2

Zen Oceanfront Chalet- Hot Tub & Sauna

NEW Luxe Church Hot Tub 3 Beds Sleeps 6 Kentville

Welcome to Piper's Perch - 10 Mins To The Ski Hill

The Tidal Fox Retreat-Oceanside Air BnB
Destinations to explore
- Halifax Holiday rentals
- Bar Harbor Holiday rentals
- Moncton Holiday rentals
- Charlottetown Holiday rentals
- Fredericton Holiday rentals
- Saint John Holiday rentals
- Bangor Holiday rentals
- Dartmouth Holiday rentals
- Ellsworth Holiday rentals
- Dieppe Holiday rentals
- Cape Breton Island Holiday rentals
- Gaspé Holiday rentals
- Cottage rentals Chester
- Rentals with outdoor seating Chester
- Cabin rentals Chester
- Family-friendly rentals Chester
- Pet-friendly rentals Chester
- Rentals with a washing machine and dryer Chester
- Rentals with beach access Chester
- Rentals with a fireplace Chester
- Rentals with a patio Chester
- House rentals Nova Scotia
- House rentals Canada
- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Dalhousie University
- Halifax Citadel National Historic Site
- Lawrencetown Beach Provincial Park
- Kejimkujik National Park & National Historic Site
- Halifax Waterfront Boardwalk
- Rainbow Haven Beach
- Conrad's Beach
- Point Pleasant Park
- Maritime Museum of the Atlantic
- Long Lake Provincial Park
- Shubie Park
- Canadian Museum of Immigration at Pier 21
- Big Mushamush Lake
- Halifax Public Gardens
- Luckett Vineyards
- Halifax Central Library
- Peggys Cove Lighthouse
- Ski Martock
- Grand-Pré National Historic Site
- Halifax Seaport Farmers' Market
- Crystal Crescent Bch Provincial Pk





