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Pet-friendly vacation rentals in Chester

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Quick stats about vacation rentals that are pet-friendly in Chester

  • Total vacation rentals

    Explore 20 vacation rentals in Chester

  • Nightly prices starting at

    Chester vacation rentals start at $157 CAD per night before taxes and fees

  • Verified guest reviews

    Over 600 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Chester vacation 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!

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

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

Outdoor spacesPetsCheckout

4.98 out of 5 average rating, 285 reviews
Top guest favourite
Bungalow in Lunenburg

Ocean Front #4 Hot Tub 2bdrm huge deck BBQ 2bath

- Oceanfront, Pier, Boat Launch, - Massive Deck: Ideal for lounging entertaining, dining, High-Top Table, BBQ, Firewall: Ensures safety and peace of mind. - Hot Tub: Unwind and enjoy the serene ocean views. - Kitchen: induction cooktop and wall oven, ideal for preparing gourmet meals. - Two Bedrooms, Two Baths: The home includes a spacious master bedroom with a king-size bed and an en suite bath. - Second Bathroom: tub for a relaxing soak. HOOKd 4 perfect retreat best of oceanfront living.

WalkabilityPetsCheck-in

5.0 out of 5 average rating, 241 reviews
Guest favourite
Home in Chester Basin

Millet Lake House • Hot Tub • Sandy Beach

Escape to Millet Lake House, a private waterfront retreat near Chester, Nova Scotia. Enjoy a sandy beach, lakefront hot tub, private dock, kayaks, SUPs and canoe. Made for family time, with two decks, a fire table, library, CD collection, board games and puzzles. Swim, paddle, read, play and reconnect. It's the kind of place where families forget their screens. SECURITY CAMERAS: Exterior cameras are located at the home's entrances only. There are no cameras inside or facing the hot tub.

Outdoor spacesConditionValue

4.93 out of 5 average rating, 215 reviews
Guest favourite
Condo in Chester

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.

PetsWalkabilityValue

4.94 out of 5 average rating, 113 reviews
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

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!

PetsOutdoor spacesGrill

4.9 out of 5 average rating, 487 reviews
Top guest favourite
An aerial view captures the serene waters of a coastal cove, surrounded by lush greenery and scattered islands. The winding road along the shoreline is lined with houses, while several boats dot the tranquil bay, enhancing the picturesque landscape.
Villa in Chester Basin

The Oaks Seaside Retreat

This beautiful oceanside 5 bedroom plus den is located in a private cove. You can lounge on gracious decks, enjoying a starry night or your morning coffee. We have the most amazing sunrises. Its a short drive to one of the several beaches. and minutes to multi-use trails, watersports, SENSEA Nordic Spa, and Chester Village. The Seaside Shanty restaurant is just seconds away. We allow 10 guests and charge $100 each for up to 2 more. Nova Scotia Tourist Accommodation - STR2425D6908

WalkabilityOutdoor spacesFamily

4.98 out of 5 average rating, 100 reviews
Top guest favourite
A spacious solarium features a cozy day bed adorned with patterned pillows. A round wooden table with chairs is situated nearby. Natural light floods the area through large glass panels, highlighting the surrounding greenery visible through the windows.
Cottage in Mahone Bay

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

Escape to Lisette’s on Long Hill, a cozy, professionally decorated two-bedroom cottage tucked away on a quiet lane in beautiful Mahone Bay. Spend your morning with a coffee in our bright solarium, stroll downtown to explore the local shops and cafés, and come home to relax in your own private space. Perfect for couples, friends or a getaway with your four-legged companion, our cottage offers a full kitchen, comfortable beds, and everything you need for a relaxing stay.

PetsWalkabilityBeach

4.93 out of 5 average rating, 110 reviews
Guest favourite
A circular hot tub is positioned on a deck overlooking the water. Clear blue skies and scattered clouds are visible above a calm water surface. Comfortable outdoor seating is arranged nearby, creating a tranquil setting for relaxation and enjoyment of the beautiful waterfront view.
Bungalow in Lunenburg

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.

PetsOutdoor spacesGrill

4.9 out of 5 average rating, 147 reviews
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 Hubbards

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.

Outdoor spacesWalkabilityCleanliness

4.97 out of 5 average rating, 152 reviews
Guest favourite
A charming yellow cottage features three windows adorned with flower boxes, complemented by a bright red door. Two blue Adirondack chairs sit on the porch, surrounded by greenery, providing a welcoming outdoor space for relaxation.
Cottage in Mahone Bay

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!

WalkabilityPetsCheck-in

4.92 out of 5 average rating, 111 reviews
Superhost
A sauna space features warm wooden walls and benches, creating a serene environment. Natural light filters in through a large window, illuminating a small basket of stones. The simplicity of the design emphasizes a calming retreat for relaxation.
Home in Hubbards

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.

Outdoor spacesWalkabilityBackyard

4.87 out of 5 average rating, 155 reviews
Guest favourite
Bungalow in Chester Basin

Ocean Front Home Chester Basin

Mini Home private Quiet area with ocean view. Large Deck Everything you need dishes, pots pans, washer and dryer, dishwasher, One double bed, one queen size bed, 2 full bathroom Master Bathroom with shower, Bathroom 2 regular tub/shower. Pets are welcome if the humans are well behaved. Halifax 45 minutes, 10 minute to Chester, 15 minutes to New Ross, or Town of Mahone Bay, Lunenburg 25 minute, Airport Halifax 1 hour ,

WalkabilityPetsAccuracy

4.92 out of 5 average rating, 132 reviews

Popular amenities for Chester pet-friendly home rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly house rentals

Top guest favourite
An aerial view of the oceanfront property showcases two distinct units along the water's edge, surrounded by lush greenery. The shoreline forms a gentle curve, leading to a hot tub area in view. Clear waters reflect the sky, providing a serene backdrop to the expansive scene.
Home in Hubbards

Oceanfront | Hot Tubs | Sauna | Gym | Game Rooms

WalkabilityOutdoor spacesAccess

4.97 out of 5 average rating, 106 reviews
Top guest favourite
The exterior of a modern home is shown at dusk, with a vibrant sunset illuminating the sky in shades of pink and orange. A spacious deck extends from the house, featuring seating arrangements for relaxation, while a field of wildflowers occupies the foreground.
Home in LaHave

The Lookout - Cottage

PetsOutdoor spacesAccuracy

4.97 out of 5 average rating, 122 reviews
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 Peggys Cove

Peggy's Cove - Modern Home with Lighthouse View

WalkabilityOutdoor spacesAccess

4.89 out of 5 average rating, 177 reviews
Top guest favourite
A historic church building is featured, showcasing vibrant yellow exterior walls and a striking red steeple. Inside, a spacious living area is equipped with several colorful couches, decorative pillows, and a wood stove, all illuminated by natural light streaming through large windows.
Home in Dayspring

South Shore Sanctuary : Historic Church w/ Hot Tub

Outdoor spacesPetsComfort

4.89 out of 5 average rating, 143 reviews
Top guest favourite
Home in Kingsburg

The Beach Barn + Cedar Sauna

Outdoor spacesPetsGrill

4.96 out of 5 average rating, 135 reviews
Top guest favourite
A spacious two-story house features a light grey exterior with white trim. A bright yellow front door welcomes guests, while a set of steps leads to the entrance. Colorful chairs are positioned on either side of the entrance, and a grassy yard surrounds the structure.
Home in Lunenburg

The Fisherman's Rustic Cottage

PetsOutdoor spacesHiking

4.96 out of 5 average rating, 185 reviews
Top guest favourite
An aerial view captures the stunning coastal landscape, featuring a winding road surrounded by lush greenery and the sparkling waters of Prospect Bay. Small islands dot the horizon, adding to the natural beauty of the seaside scenery in Nova Scotia.
Home in Lower Prospect

Modern NS Four-square inspired Lighthouse

PetsWalkabilityBackyard

4.91 out of 5 average rating, 157 reviews
Top guest favourite
A geodesic dome structure is situated among trees, featuring large windows that offer views of the surrounding woods. Adjacent to the dome is a wooden sauna. A spacious deck is equipped with seating and a wrapped railing, enhancing the outdoor experience.
Home in Seabright

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

PetsOutdoor spacesHot tub

4.98 out of 5 average rating, 223 reviews

Pet-friendly home rentals with a pool

Top guest favourite
A private hot tub is situated beside a cozy seating area with a sofa under warm lighting. Adjacent, a wooden sauna stands, adding a tranquil touch. The area features a soft green lawn, illuminated by subtle lights, creating an inviting outdoor space.
Guest suite in Hammond Plains

Luxury Lakefront Suite - Hot Tub & Amenities!

Outdoor spacesWalkabilityAccess

4.97 out of 5 average rating, 544 reviews
Guest favourite
A spacious wooden deck features a hot tub surrounded by trees, emphasizing a natural setting. Two comfortable lounge chairs are positioned nearby, and a stylish black barbecue grill is available. Floor-to-ceiling windows showcase the peaceful interior, seamlessly connecting outdoor and indoor spaces.
Cabin in Lunenburg

Lakefront Luxury Retreat

PetsOutdoor spacesAccuracy

4.96 out of 5 average rating, 116 reviews
Top guest favourite
Home in Halifax

Seacliff - Luxury Waterfront Paradise - Pool & Spa

PetsOutdoor spacesCheck-in

4.9 out of 5 average rating, 133 reviews
Guest favourite
The four Shobac Cabins are silhouetted against a twilight sky, their windows glowing warmly. Reflections of the cabins are seen in a calm pond, surrounded by grass and low shrubs. Trees in the background indicate the natural setting of the property.
Cottage in Lunenburg

Seaside Hirtle's Cottage - A Stunning Retreat

Outdoor spacesPetsBeach

4.97 out of 5 average rating, 70 reviews
Top guest favourite
A salt water pool is surrounded by landscaped grounds featuring natural rock formations and greenery. Several lounge chairs and umbrellas provide shaded seating. In the background, a spacious property showcases a modern building set against a clear sky, with a pathway leading up to it.
Apartment in Shad Bay

The Eyrie, an eagles nest with an amazing view.

Outdoor spacesPetsAccess

5.0 out of 5 average rating, 65 reviewsAn aerial view of the Italian-inspired home reveals its striking architecture surrounded by lush landscaping. A winding driveway leads to the property, while a stone patio encircles the in-ground pool, offering an inviting space for outdoor relaxation amidst the greenery.
Home in Williamswood

Tranquil Chateau on Moody Lake

Outdoor spacesPetsComfort

4.68 out of 5 average rating, 72 reviews
Top guest favourite
The historic home is showcased from a distance, featuring a large front porch with white railings and colorful flower pots. The exterior is painted in soft tones, highlighting the architectural details. Surrounding greenery enhances the natural setting of the property.
Home in Pentz

Riverhouse in Pentz

PetsOutdoor spacesView

4.95 out of 5 average rating, 87 reviews
Guest favourite
A cozy kitchen area features wooden cabinetry, complemented by a dining table set for four. A ladder leads to a loft space, while natural light fills the room through window treatments. The open layout connects to a welcoming living area with a sofa.
Cottage in Hubbards

Bayswater Cottage- Anchorage House & Cottages

Outdoor spacesPetsAmenities

4.92 out of 5 average rating, 51 reviews

Private, pet-friendly home rentals

Top guest favourite
An open concept living area features vaulted ceilings with exposed beams. Large windows illuminate the space, providing views of the surrounding forest. A modern kitchen with sleek appliances is adjacent to a cozy seating arrangement, which includes a leather sofa and stylish chairs.
Cottage in Chester

Serene Cottage on 10 acres, Hot Tub, Lake Access

WalkabilityOutdoor spacesBathroom

4.97 out of 5 average rating, 120 reviews
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

Lakeside Cottage in Chester | BBQ + Lake Access

PetsOutdoor spacesQuiet

4.96 out of 5 average rating, 210 reviews
Guest favourite
Apartment in Chester Basin

Chester Basin Place

PetsWalkabilityDecor

4.9 out of 5 average rating, 106 reviews
Top guest favourite
Cottage in Wentzells Lake

The Lazy Loon Lake House

Outdoor spacesPetsValue

4.98 out of 5 average rating, 120 reviews
Top guest favourite
The modern chalet is nestled among tall trees, featuring a wooden exterior and large windows that invite natural light. A spacious deck is visible, furnished with outdoor seating and a grill, offering a serene view of the surrounding forest.
Tiny homes in Petite Rivière

Peaceful, private, forest hideaway for two

WalkabilityOutdoor spacesGetting around

4.93 out of 5 average rating, 350 reviews
Guest favourite
A charming cabin is illuminated by warm string lights in the evening. A winding path leads up to the deck, while chairs invite guests to sit and relax. The porch is accessorized with an umbrella, adding to the cozy outdoor ambiance.
Cabin in Windsor

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

WalkabilityOutdoor spacesDecor

4.96 out of 5 average rating, 228 reviews
Top guest favourite
Cottage in Greenfield

The Harmony Grand at Molega Lake

Outdoor spacesWalkabilityComfort

4.99 out of 5 average rating, 222 reviews
Top guest favourite
An aerial view reveals a serene island surrounded by calm waters, with lush greenery and rocky shorelines. Kayaks and a canoe are visible along the water's edge, alongside an outdoor seating area under the trees, ideal for enjoying the ocean views.
Island in Port Medway

the ISLAND - A Charming Island Cottage and Bunkie

Outdoor spacesWalkabilityAir conditioning

4.98 out of 5 average rating, 213 reviews

Destinations to explore