
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$12,555 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.

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.

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!

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.

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.

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.

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

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.

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

White Point Resort - Panoramic Ocean View

Half Moon Cove Retreat

All Decked Out in Mahone Bay

Halifax Harbour View | Spacious Luxury + Pool

Bayswater Beach Retreat - 4 bdrm w/ hot tub

North End Nest

Beautiful new 6 bedroom lakehouse close to Halifax

Halifax Private Luxury Retreat w/Hot Tub & Pool
Weekly house rentals

Witmere

Endeavour Cottage

Orig.Inns - The Barn Retreat & Hot Tub

The Whale House

Lovely oceanfront home w/4 BR + stunning views

Gorgeous Oceanfront Estate in Peggy’s Cove

Zen Oceanfront Chalet- Hot Tub & Sauna

White Rock Retreat · Annapolis Valley
Private house rentals

Private Oceanfront Escape

Lake house on Little Mush Mush

Charming Chester cottage a stone’s throw from spa

The old cape

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

Luxury Beachfront Villa, Cleaveland Beach 71

Mahone Bay Ocean View 4BR Heritage House + Yard

Oak Island Cottage with HOT TUB
Destinations to explore
- Halifax Vacation rentals
- Bar Harbor Vacation rentals
- Moncton Vacation rentals
- Charlottetown Vacation rentals
- Fredericton Vacation rentals
- Saint John Vacation rentals
- Bangor Vacation rentals
- Dartmouth Vacation rentals
- Ellsworth Vacation rentals
- Lunenburg Vacation rentals
- Dieppe Vacation rentals
- Southwest Harbor Vacation rentals
- Rentals with beach access Chester
- Rentals with outdoor seating Chester
- Cottage rentals Chester
- Rentals with a washer and dryer Chester
- Rentals with a fireplace Chester
- Pet-friendly rentals 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
- Dalhousie University
- Kejimkujik National Park & National Historic Site
- Lawrencetown Beach Provincial Park
- Rainbow Haven Beach
- Conrad's Beach
- Halifax Waterfront Boardwalk
- Point Pleasant Park
- Maritime Museum of the Atlantic
- Shubie Park
- Long Lake Provincial Park
- Canadian Museum of Immigration at Pier 21
- Big Mushamush Lake
- Halifax Public Gardens
- Luckett Vineyards
- Halifax Central Library
- Halifax Seaport Farmers' Market
- Peggys Cove Lighthouse
- Ski Martock
- Grand-Pré National Historic Site
- Crystal Crescent Bch Provincial Pk





