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.

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Top guest favourite
A serene lakefront view captures the luxury lake house surrounded by trees. The structure reflects gently in the calm water, showcasing warm tones from the setting sun. A private beach area with sand and a dock is visible, enhancing the tranquil atmosphere.
Cottage in Hubbards
4.98 out of 5 average rating, 256 reviews

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

Top guest favourite
A private chalet is nestled among bare trees, with warm light glowing from the windows. String lights adorn the deck, enhancing the wintery scene of fresh snow covering the ground. The cabin's rustic wooden exterior complements the tranquil woodland setting.
Cabin in Windsor
4.97 out of 5 average rating, 194 reviews

Ski Martock Chalet w Fire Pit + Movie Nights

Ski by day, unwind with crackling fires, movies & games by night. 15 minutes to Ski Martock & Bent Ridge Winery, 1 hour to Halifax. This cozy lakefront cottage is the perfect winter basecamp. Warm up by the fire pit, stream a movie on the projector, spin a record. This is your time to relax & reconnect. Pet friendly, fast wifi, tucked in the woods, and set on a quiet lake with private dock. Only 1 hour to Halifax . Expect snowy views, starry nights, and that “wish we had one more night” feeling.

Top guest favourite
A spacious living area features contemporary leather sofas arranged around a low coffee table. Large glass garage doors provide abundant natural light and views of the exterior. A wooden dining table and chairs are visible in the background, enhancing the sense of openness.
Flat in Lunenburg
4.87 out of 5 average rating, 175 reviews

Architecturally-designed: The Rosebay, B2 Lofts

THE ROSEBAY AT B2 LOFTS is located in a newly renovated historic 1800s building adjacent to the Lunenburg Harbour in the heart of the UNESCO World District. Designed by internationally celebrated Brian MacKay-Lyons this charming 1-bedroom apartment is located on ground level, is wheelchair accessible and has a sprinkler system. The great room features: 13.5' ceiling, Belgian wood stove, huge glarage door that opens to breathtaking views of the Lunenburg Harbour, and a pull-out sofa bed.

Guest favourite
A modern kitchen area features light blue walls and wooden beams. An island with rustic details is accompanied by two dark bar stools. A floral armchair sits nearby, and shelves display dishware. Natural light enters through multiple windows, creating a bright and inviting space.
Cabin in Mahone Bay
4.91 out of 5 average rating, 472 reviews

Quarrie Cottage | Mahone Bay

This newly constructed Main Street cottage is steps away from all the main attractions, while also being set back from the road enough to give guests a private and tranquil place to retreat at the end of the day. We are just across the street from Saltbox Brewery, with a beautiful patio, frequent musical guests and visiting food trucks. The cottage itself is an open and breezy ,featuring French doors, rustic details and a cozy wood stove- making it suitable for getaways all year long!

Top guest favourite
A welcoming porch is adorned with two light blue adirondack chairs, positioned to overlook a serene lake. The ground is covered in vibrant autumn leaves, and trees in the background are reflected in the calm water. The scene captures a peaceful outdoor retreat.
Cottage in Chester
4.96 out of 5 average rating, 175 reviews

Cozy Lakefront Cottage w/ wood stove near Martock

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.

Top guest favourite
A charming boathouse is positioned on a wooden dock, surrounded by lush greenery. The elevated deck features a glass railing, offering unobstructed views of the water. Two wooden benches provide seating, inviting relaxation in the serene seaside setting.
Cottage in Chester
4.95 out of 5 average rating, 111 reviews

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.

Top guest favourite
The serene lake is bordered by trees and reflects a clear blue sky. A dock with two blue chairs extends into the water, and a floating device is visible nearby. The calm surface of the lake enhances the peaceful ambiance.
Home in Chester Basin
4.96 out of 5 average rating, 160 reviews

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.

Top guest favourite
An aerial view of the oceanfront property alongside a rocky shoreline reveals a spacious lawn and several nearby homes. The scene includes vibrant green grass and red outdoor chairs positioned near the water, complemented by the dramatic coastal landscape of Peggy's Cove.
Home in Peggy's Cove
4.89 out of 5 average rating, 146 reviews

Peggy's Cove - Modern Home with Lighthouse View

Forget your worries in our spacious and serene oceanfront 3 bedroom home with stunning views of Peggy's Cove and the ocean! Our beautiful home can sleep up to 7 guests comfortably and includes many features such as a BBQ, fire table, outdoor deck with views of the ocean, & seating right near the water. We are a short walk to Peggy's Point, Peggy's Point Lighthouse, & many other places on the cove like shops, restaurants, hiking trails & nature parks. Enjoy your stay!

Top guest favourite
A dining area is showcased with a wooden table surrounded by six metal chairs. Natural light filters in through a large window, highlighting the beam ceiling and stone accents. A decorative bowl rests at the center of the table, complemented by a plant and surfboards nearby.
Cottage in Queensland
4.98 out of 5 average rating, 126 reviews

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.

Superhost
A close-up view of a vintage brass doorknob is featured, leading into a well-lit bedroom. The soft white bedding is neatly arranged on the spacious bed, with a dark accent pillow enhancing the serene atmosphere. A small plant sits beside the bed, adding a touch of greenery.
Home in Mahone Bay
4.91 out of 5 average rating, 135 reviews

Welcome to the Cozy Quilt

Welcome to the Cozy Quilt! A focal point of the Main Street and located in the heart of Mahone Bay. It’s sits across from the government wharf where you are only a short stroll to the cafes, brewery, pub, restaurants and shops. What started as part of the general store in 1867, the residence was later removed from the store and moved to its current home at 664 Main Street. Since 2003 it has been home to the Quilt Shop which help inspired the name Cozy Quilt.

Top guest favourite
The exterior of the architecturally unique cottage is showcased in the twilight. The structure features large windows and a sleek design, elevated on supports. Surrounded by natural landscapes, two chairs are positioned on the deck, offering a space to enjoy the views.
Home in Terence Bay
4.89 out of 5 average rating, 246 reviews

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.

Top guest favourite
Home in Lunenburg
4.94 out of 5 average rating, 176 reviews

OceanFront #12 HotTub Private Deck waterfront BBQ

Take it easy at this unique and tranquil getaway.and a waterfront deck brimming with amenities. Enjoy the comforts of home and beyond with air-conditioning, a fire pit, and more in this private community oasis. Complete with a private pier and boat launch, HOOK'd 12 invites you to experience waterfront living at its finest, just moments away from the heart of Lunenburg village.

Popular amenities for Chester pet-friendly home rentals

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 $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 520 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 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!

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