
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

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

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.

Wilson's Coastal Club - C5
Beautiful oceanfront 1-bedroom cottage with a King bed. Enjoy the deck with a propane BBQ, patio furniture, and stunning views of St. Margaret's Bay. The bathroom features a 2-person jet tub and separate shower. Free high-speed Wi-Fi and Internet TV included. Additionally, guests can add on our unique wood-fired hot tub experience for an extra fee. See “Other things to Note” for details. Feel free to reach out with any pricing questions as Airbnb doesn't always show all available rates.

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!

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.

The Old Kettle Cabin with Hot Tub
Get cozy and settle in to this inviting space with your significant other, or getaway by yourself for some sought after rest and relaxation. Nestled privately off the road, the cabin offers beautiful views of the Historic Medway River in a tranquil nature setting. Watch the tide come in and out from the large deck, or venture out into the many trails nearby on the electric bikes. This space encourages both adventure and relaxation, and will be sure to bring you and yours closer.

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.

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.

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.

Ocean Front #3 HotTub Sunset RoofTopDeck BBQ 2bath
Waterfront Cottage: Huge deck, sun sets, Private Hot Tub: 6 Person tub for 2. Panoramic Water Views: Modern Cabin: privacy and a peaceful environment. Large Deck: outdoor living space both you can take in the sun or retreat into the share. Nature Retreat with wildlife Romantic Escape: for couples, Heated floors, Shower tower, queen master, an extra guest could sleep on the couch. Super private chefs kitchen. Well equipped for all seasons.

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.
Popular amenities for Chester pet-friendly home rentals
Pet-friendly house rentals

Witmere

Ocean front cottage, Mahone Bay

a private oasis

Dog Friendly 3 Bedroom Lake House Fenced-In Yard

Cottage on the Cove

Windrose Cottage welcomes you

Stunning Island Home Above Treetops Near Lunenburg

Serenity by the Sea
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

Fox Point Cottage - Anchorage House & Cottages

Riverhouse in Pentz

Bayswater Cottage- Anchorage House & Cottages

Home Away from Home - Entire Apartment

The Eyrie, an eagles nest with an amazing view.
Private, pet-friendly home rentals

Chester Basin Place

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

Seawind Cottage

The Lazy Loon Lake House

Oceanfront Escape + Hot Tub | Near Lunenburg

Private Cottage - Hot tub Woodstove on 10 Acres

5 Star Lakefront Cottage on Tranquil Hennigar Lake

Wildberry Cottage
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!
Destinations to explore
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- Rentals with outdoor seating Chester
- House rentals Chester
- Cabin rentals Chester
- Rentals with a washing machine and dryer Chester
- Family-friendly rentals Chester
- Cottage rentals Chester
- Rentals with a fireplace Chester
- Rentals with beach access Chester
- Rentals with a patio Chester
- Pet-friendly rentals Nova Scotia
- Pet-friendly rentals Canada
- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Conrad's Beach
- Lawrencetown Beach Provincial Park
- Ski Martock
- Canadian Museum of Immigration at Pier 21
- Point Pleasant Park
- Halifax Public Gardens
- Maritime Museum of the Atlantic
- Halifax Central Library
- Dalhousie University
- Luckett Vineyards
- Kejimkujik National Park & National Historic Site
- Halifax Waterfront Boardwalk
- Fisherman's Cove
- Crystal Crescent Bch Provincial Pk
- Shubie Park
- Grand-Pré National Historic Site
- Museum of Natural History
- Big Mushamush Lake
- Peggys Cove Lighthouse




