
Pet-friendly holiday rentals in Chester
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Chester
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

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 #3 HotTub Sunset RoofTopDeck BBQ 2bath
Ocean front cozy retreat just 3km from the charming Historic Town of Lunenburg! This serene getaway is perfect for relaxing and recharging. Enjoy a hot tub under the stars, a BBQ for delightful evenings, and spacious decks for sunbathing or quiet reflection. All the amenities you need and a few extras, it’s an ideal spot for creative minds and couples to enjoy ignite their spark. Whether you're planning to write your next film or simply unwind near wildlife, book your unforgettable stay today!

Orig.Inns - Cozy Bunkie Hideaway with Hot Tub
Unwind and relax near the stunning beaches and charming cafés on the South Shore. Tucked away surrounded by trees, this cozy retreat offers all the comforts you need for a perfect getaway. Listen to a record, cook a delicious meal, snuggle up with a movie, soak in the hot tub, stargaze under the clear night sky, and listen to the peepers. Just a 5–10 minute drive away, you’ll find Crescent Beach, Rissers Beach, Ploughman’s Lunch Café, Osprey Nest Pub, and the Lahave Bakery. Follow us @Orig.Inns

The Oasis on Blueberry Lane
Enjoy swimming or kayaking in our beautiful lake. Afterwards, hop in the hot tub to relax your tired muscles, then roast marshmallows over the firepit or have a game of pool. You can also curl up next to wood stove for a lazy evening in. Take a short drive to one of the several stunning beaches. Enjoy being 10 minutes from both SENSEA Nordic Spa, and Chester Village - where you'll find Chester Golf Course, a selection of restaurants, cafes, and shops. Only 30 minutes to ski Martock!

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.

Large Pet Friendly Lakefront cottage in Chester
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 Boathouse on Scotch Cove
This little boathouse sits right on Scotch Cove in East Chester, NS. Enjoy seaside views from every angle, with lovely outdoor seating and propane BBQ. The deck leads directly to the dock allowing for easy access for swimming or watercraft provided. The place is just a short walk from hiking and biking trails, with nearby lakes and sandy beaches. The indoor projector and screen make movie nights so much better! The boathouse is fully equipped for winter with a cozy woodstove.

Glamping Dome 2 StarGazer
Welcome to Board & Batten in beautiful Rose Bay, Nova Scotia. Sitting on a cliff overlooking the ocean, this breathtaking property is home to four, individually rented, geodesic glamping domes and two premium cottages (coming soon). Each identical dome offers a breathtaking view of the ocean and the night sky, as well as everything you’ll need for a luxury stay (this isn’t camping, it's glamping!). The domes and cottages are set nicely apart to allow a feel of privacy.

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.

Mid Century Aframe, Hot Tub, and Beach Access
The perfect location to explore the very popular South Shore of Nova Scotia. Close to beaches, cafes, restaurants, charming fishing villages and many other amenities. This vintage inspired Aframe sits on its own private lot with huge ocean views, beautiful private hot tub and luxury interior finishes. A note that the nights between now and May 9, 2025 are discounted because the sliding door is not in operation. It will be fixed after May 9.

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.

Stunning, secluded chalet with wood fired hot tub
Enjoy the peaceful, wooded setting of this beautifully-appointed chalet. Tucked amongst the tall pines along Petite Rivière, the chalet marries modern amenities with comfort and tranquility. It is ideally situated within a short walk or drive to beautiful beaches and excellent surfing. Dining, museums, and local art galleries are also just minutes away.
Popular amenities for Chester pet-friendly home rentals
Pet-friendly house rentals

Nordic Tides Retreat Sauna & Spa

The Whale House

a private oasis

Harbour-side home ocean views/work from home

Private Lakefront Escape|Swim, Sip Wine & Stargaze

The Lookout

Dog Friendly 3 Bedroom Lake House Fenced-In Yard

Cottage on the Cove
Pet-friendly home rentals with a pool

East River Cottage- Anchorage House & Cottages

2-storey designer cottage - Shobac Farm Gate House

Tranquil Chateau on Moody Lake

Riverhouse in Pentz

Bayswater Cottage- Anchorage House & Cottages

Home Away from Home - Entire Apartment

The Eyrie, an eagles nest with an amazing view.

Salty SeaScape 4 Bed OCEAN-VIEW Home with SWIM SPA
Private, pet-friendly home rentals

The Library at Orchard House

Chester Basin Place

Charming Chester cottage steps from Nordic spa

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

Seawind Cottage

The Margaret of Hubbards Apt 1 - 7 Person Hot Tub

Hot Tub, private 10 acres, trails, Woodstove

Welcome to The Loch
Quick stats about holiday rentals that are pet-friendly in Chester
Total rentals
20 properties
Nightly prices starting at
$104 SGD before taxes and fees
Total number of reviews
500 reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Destinations to explore
- Halifax Holiday rentals
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- Mid-Coast, Maine Holiday rentals
- Charlottetown Holiday rentals
- Fredericton Holiday rentals
- Saint John Holiday rentals
- Lunenburg County Holiday rentals
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- Rentals with beach access Chester
- Rentals with a fireplace Chester
- House rentals Chester
- Rentals with a patio Chester
- Rentals with outdoor seating Chester
- Cabin rentals Chester
- Family-friendly rentals Chester
- Rentals with a washing machine and dryer Chester
- Cottage rentals Chester
- Pet-friendly rentals Nova Scotia
- Pet-friendly rentals Canada
- Cresent Beach
- Rissers Beach Provincial Park
- Crescent Beach, Lunenburg County, Nova Scotia
- Atlantic Splash Adventure
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Beach Meadows Beach
- Bayswater Beach Provincial Park
- Chester Golf Club
- Conrad's Beach
- Cape Bay Beach
- Splashifax
- Lawrencetown Beach
- Canadian Museum of Immigration at Pier 21
- Hunts Point Beach
- The Links at Brunello
- Lawrencetown Beach Provincial Park
- Point Pleasant Park
- Halifax Public Gardens
- Maritime Museum of the Atlantic
- Little Rissers Beach
- Oxners Beach
- Halifax Central Library