
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$12,547 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.

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!

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.

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.

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, 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 Chester house rentals
House rentals with a pool

Half Moon Cove Retreat

All Decked Out in Mahone Bay

Tranquil Chateau on Moody Lake

Halifax Harbour View | Spacious Luxury + Pool

Bayswater Beach Retreat - 4 bdrm w/ hot tub

North End Nest

Oceanview Luxury Estate - Magazine Perfect!

Beautiful new 6 bedroom lakehouse close to Halifax
Weekly house rentals

Endeavour Cottage

Home in the Heart of Chester

The Whale House

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

Luxury Oceanfront Cottage-Rose Bay, Lunenburg #2

Zen Oceanfront Chalet- Hot Tub & Sauna

The old cape

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

Windrose Cottage welcomes you

Mahone Bay Ocean View 4BR Heritage House + Yard
Destinations to explore
- Halifax Vacation rentals
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- Gaspé Vacation rentals
- Cottage rentals Chester
- Rentals with outdoor seating Chester
- Cabin rentals Chester
- Family-friendly rentals Chester
- Rentals with a washer and dryer Chester
- Pet-friendly rentals 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
- Kejimkujik National Park & National Historic Site
- Lawrencetown Beach Provincial Park
- Halifax Waterfront Boardwalk
- Conrad's Beach
- Rainbow Haven Beach
- Point Pleasant Park
- Long Lake Provincial Park
- Maritime Museum of the Atlantic
- Shubie Park
- Big Mushamush Lake
- Canadian Museum of Immigration at Pier 21
- Halifax Public Gardens
- Luckett Vineyards
- Halifax Central Library
- Ski Martock
- Peggys Cove Lighthouse
- Grand-Pré National Historic Site
- Halifax Seaport Farmers' Market
- Crystal Crescent Bch Provincial Pk





