
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 $142 SGD 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 & 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!
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

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.

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.

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.

"Lisette's on Long Hill", cozy with boho charm
The moment you walk through the door, you are treated with your own oasis -- a spacious solarium with a cozy day bed tucked in the corner waiting for you to relax, or sit at the table and play a game of tic-tac-toe. This two-bedroom professionally decorated charmer has brand new queen and double beds with hotel linen and lots of pillows. Need to work a bit? Use our cozy office nook. Welcome to Lisette's on 66 Long Hill. HST IS INCLUDED IN PRICE

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.

Koko Bay: Glamping, where glamour meets nature!
Escape the ordinary at KoKo Bay—an adults-only glamping retreat near Hubbards! Sleep in luxury, wake to ocean breezes, and stargaze by the fire. With epic views, fine linens, and direct access to Rails to Trails, it’s the perfect mix of wild and wonderful. Beach days, bike rides, and total unplugged bliss await. Romantic, peaceful, and unforgettable. (Yes, nature’s guests—bugs & critters—may drop by!!) it's part of the magic!

Lakeview Cottage | Fox Point Lake | Hot tub/Kayaks
Welcome to our charming Lakeview cottage on Fox Point Lake in Hubbards, NS! This rustic log home boasts 3 bedrooms and 1.5 baths, making it perfect for families or friends seeking a peaceful retreat. Enjoy our private dock on the lake and take advantage of kayaks for fun-filled water adventures (seasonal). Unwind, reconnect with nature, and create cherished memories. Book now for an unforgettable lakeside getaway!

The Beach Barn + Cedar Sauna
The Beach Barn is 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

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

Ocean front cottage, Mahone Bay

The Whale House

The Lookout - Cottage

a private oasis

2 Bed, 1 Bath Cottage on Hirtle Lake (6 guests)

Dog Friendly 3 Bedroom Lake House Fenced-In Yard

Beachfront 3 Bdr, 2 Bath Home 20 min frm Halifax

Sunny Sanctuary in Martin's River
Pet-friendly home rentals with a pool

Lakefront Luxury Retreat

2-storey designer cottage - Shobac Farm Gate House

Tranquil Chateau on Moody Lake

Fox Point Cottage - Anchorage House & Cottages

Riverhouse in Pentz

Seaside Hirtle's Cottage - A Stunning Retreat

The Eyrie, an eagles nest with an amazing view.

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

Waterfront cottage, private beach, LaHave River.

Mallard on Church Lake Accessible Lakefront AFrame

White Cottage

Captain's Quarters - 2 bedroom harbourview condo

the ISLAND - A Charming Island Cottage and Bunkie

Charming Historic Cottage on Main in Mahone Bay

The Harmony Grand at Molega Lake

Private cabin on a lake - kayaks, SUP, fire pit
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
- Dartmouth Holiday rentals
- Ellsworth Holiday rentals
- Cape Breton Island Holiday rentals
- Dieppe Holiday rentals
- Gaspé Holiday rentals
- House rentals Chester
- Cottage rentals Chester
- Rentals with outdoor seating Chester
- Cabin rentals Chester
- Family-friendly rentals Chester
- Rentals with a washing machine and dryer Chester
- Rentals with beach access Chester
- Rentals with a fireplace Chester
- Rentals with a patio Chester
- Pet-friendly rentals Nova Scotia
- Pet-friendly rentals Canada
- Rissers Beach Provincial Park
- Oak Island
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Lawrencetown Beach Provincial Park
- Kejimkujik National Park & National Historic Site
- Conrad's Beach
- Rainbow Haven Beach
- Long Lake Provincial Park
- Big Mushamush Lake
- Point Pleasant Park
- Shubie Park
- Maritime Museum of the Atlantic
- Halifax Public Gardens
- Luckett Vineyards
- Halifax Central Library
- Ski Martock
- Halifax Seaport Farmers' Market
- Crystal Crescent Bch Provincial Pk
- Scotiabank Centre
- Museum of Natural History
- Sir Sandford Fleming Park
- Fisherman's Cove
- Bayswater Beach Provincial Park





