
Pet-friendly holiday rentals in Chester
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Chester

Total holiday rentals
Explore 20 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at $185 NZD per night before taxes and fees

Verified guest reviews
Over 600 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
20 of Chester holiday 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 pet-friendly home rentals in Chester
Guests agree: These pet-friendly homes are highly rated for location, cleanliness and more.

Serene Cottage on 10 acres, Hot Tub, Lake Access
GREENWOOD COTTAGE - 10min drive from Chester. Nestled on 10 acres of private forest, Greenwood Cottage awaits. If you seek an escape from the city, this 3 king sized bedrooms, on one level - 20ft vaulted ceilings in the Main living area. It is perfect for families, friends and couples. After a long day exploring, hiking or visiting Chester. The Hot Tub will be welcomed or cozy on up to the woodstove with your loved ones. Sensea Spa , Chester, Lunenburg and Mahone Bay are a short drive away

Fox Point Lake House - Luxury Lakefront Rental!
Featured on Home Shores - Season 2, Episode 1! This one of a kind luxury lake house has plenty to offer. Gorgeous lakefront, private beach, hot tub that overlooks the lake, water views from the main floor and primary bedroom, wood fireplace and the list goes on. Other features include: - 30 mins from Halifax - Cathedral ceilings with A frame front - Built in wet bar with wine and beer fridge - Private sand beach - Salt water hot tub that comfortably sits 7 Check our IG - @foxpointlakehouse

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!

Luxury Lakefront Suite - Hot Tub & Amenities!
Executive Lakefront Retreat: Escape to our luxurious and private two bedroom (plus den) apartment above the garage, boasting exclusive amenities for a serene stay. Enjoy: Private Hot Tub & Outdoor Propane Fireplaces Swimming Pool & Full Outdoor Kitchen Water Activities: Kayak, paddle boat, fishing rods, and dock access Nearby Conveniences: Within 5 km, find Tim Hortons, supermarket, drug store, liquor store, gas station Convenient Location: Just a 20-minute drive to downtown Halifax.

Captain's Quarters - 2 bedroom harbourview condo
Located in the heart of sea-side Chester, Nova Scotia with a gorgeous, full view of the front harbour. The Captain’s Quarters is a bright and beautifully finished, spacious, 2-bedroom condo that is central to all that scenic Chester has to offer. Walking distance to the pubs, restaurants, bakery, yacht club & much more! Large, floor-to-ceiling windows offer a perfect view of Mahone Bay. Less than a 5-minute drive to Sensea Nordic Spa - a perfect home base for your South Shore stay.

Spacious Lakefront Cottage Retreat
This pet friendly, four season cottage is the perfect space to escape the city with a loved one for a weekend or for your next family vacation! Only 50 minutes from Halifax, it’s in perfect proximity between downtown Chester and Windsor. The home Includes a large eat in kitchen with sitting area, bathroom, laundry and two bedrooms on the main level and a walkout primary bedroom and large living room with wood stove on the lower level and a large walk out deck overlooking the lake.

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.

Oceanfront #6 Hot tub sun sets huge deck BBQ 2 bed
Nate’s Nest is super close to the Historic town of Lunenburg Huge deck outdoor living Hot tub, Sun Sets Waterfront Ocean views quite charming unit with 2 baths modern kitchen & Den for friends to visit. HOOKd home Nestled in a very rare community lil HOOK Properties inclusive of a private pier boat launch and like minded people who enjoy living on the water A water lovers dream Wake up to sparkly water shimmering into your windows or enjoy star gazing in the hot tub.

The Beach Loft: 5-bedroom
This pretty beach house is located just steps from the beautiful Seawall beach. Relax in the hot tub, hammock or next to the fire. The perfect getaway that is only 34min from Halifax. Featuring a wood burning fireplace and stone accents. Private hot tub overlooking the ocean. Post and beam Construction. Ocean views. Seawall beach is between Queensland and Cleveland’s beach. Also located on Rails to Trails path. Minutes to restaurants and coffee shops in Hubbards.

Charming Historic Cottage on Main in Mahone Bay
Cottage on Main is centrally located in the heart of town across from the harbour wharf in beautiful Mahone Bay. It is within walking distance of extraordinary local shops, restaurants, cafes, local brewery, grocery store and more. Enjoy this charming property all to yourself and all that the town has to offer! Want to see different views of Mahone Bay? We have 2 bikes and 2 paddle boards available for guest use. The trails are handy and the water is calm!

Nordic Tides Retreat Sauna & Spa
Welcome to Nordic Tides, a private oceanfront home on Nova Scotia’s rugged coastline with wide Atlantic views, warm modern design, and space to gather with family and friends. The home includes a cedar sauna, outdoor hot tub, fire pit, BBQ, billiards table, and generous indoor and outdoor areas. It is ideal for guests looking for a quiet coastal escape, time together, and a comfortable place to relax after exploring Hubbards and the surrounding beaches.

The Beach Barn + Cedar Sauna
The Beach Barn and Cedar Sauna are 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
Popular amenities for Chester pet-friendly home rentals
Pet-friendly house rentals

Back Bay Cottage

The Lookout - Cottage

Peggy's Cove - Modern Home with Lighthouse View

Pet-Friendly Glamping Dome close to Peggy’s Cove!

South Shore Sanctuary : Historic Church w/ Hot Tub

Lakefront home with hot tub

Modern NS Four-square inspired Lighthouse

Orig.Inns - The Barn Retreat & Hot Tub
Pet-friendly home rentals with a pool

Lakefront Luxury Retreat

Salty SeaScape 4 Bed OCEAN-VIEW Home with SWIM SPA

Land Yacht Oceanfront Luxury + Indoor Pool Escape

Seaside Hirtle's Cottage - A Stunning Retreat

The Eyrie, an eagles nest with an amazing view.

Spectacular Waterfront Estate near Lunenburg

Riverhouse in Pentz

Tranquil Chateau on Moody Lake
Private, pet-friendly home rentals

Lovely Times Cottage - A Chester lakeside retreat

"Lisette's on Long Hill", cozy with boho charm

Peaceful, private, forest hideaway for two

Private cabin on a lake - kayaks, SUP, fire pit

Nova Glamping Log Cabin

Glamping Dome 1 SeaSpray

the ISLAND - A Charming Island Cottage and Bunkie

White Cottage
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
- Ellsworth Holiday rentals
- Dartmouth Holiday rentals
- Cape Breton Island Holiday rentals
- Gaspé Holiday rentals
- Lunenburg Holiday rentals
- Rissers Beach Provincial Park
- Oak Island
- Kejimkujik National Park & National Historic Site
- Hirtle's Beach
- Dalhousie University
- Lawrencetown Beach Provincial Park
- Halifax Citadel National Historic Site
- Conrad's Beach
- Big Mushamush Lake
- Long Lake Provincial Park
- Rainbow Haven Beach
- Shubie Park
- Maritime Museum of the Atlantic
- Point Pleasant Park
- Halifax Public Gardens
- Luckett Vineyards
- Crystal Crescent Bch Provincial Pk
- Canadian Museum of Immigration at Pier 21
- Ski Martock
- Halifax Central Library
- Halifax Seaport Farmers' Market
- Scotiabank Centre
- Sir Sandford Fleming Park
- Museum of Natural History





