
Pet-friendly vacation 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 Bear’s Den treehouse lodging.
Nestled in the woods, accessible year round. Very private & quiet. No hunting on this property but enjoy great fishing. Pizza & burger take-out just 10 min away. Lots of water close by for kayaking/canoeing. ATV trails just a few km away. Firewood supplied. Please bring your own drinking / wash water. Pets welcome, but Not on the furniture unless you’ve brought a cover. Never leave pets unattended. No running water. Outhouse/toilet facility. Bring your own disposable propane tank if BBQ’ing.

Wildwood Acres
Welcome to Wildwood Acres! This peaceful log cottage is located on Second Peninsula, just 6 minutes from the vibrant town of Lunenburg. With almost 3 acres and a fenced in area, your dog will be able to enjoy this spot as much as you will. Whether the occassion is a family vacation, or relaxing weekend away with your friends, this Wildwood Acres is just what you need! There are many options for dining and activities in Mahone Bay or Lunenburg, and Bachman's beach is just down the road.

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.

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.

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

The Whale House

a private oasis

Harbour-side home ocean views/work from home

Entire 1-bedroom apartment for 3

Private Lakefront Escape|Swim, Sip Wine & Stargaze

Dog Friendly 3 Bedroom Lake House Fenced-In Yard

Cottage on the Cove

Stunning Island Home Above Treetops Near Lunenburg
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

Lakefront Luxury Retreat

Chester Basin Place

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

Seawind Cottage

Welcome to The Loch

Sherbrooke Lakeside Retreat

Unique oceanfront home near Lunenburg

Mill-Cozy Cottage
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 $112 CAD per night before taxes and fees
Verified guest reviews
Over 500 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!
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- 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
- Conrad's Beach
- Cape Bay Beach
- Chester Golf Club
- Splashifax
- Canadian Museum of Immigration at Pier 21
- Lawrencetown Beach
- Hunts Point Beach
- The Links at Brunello
- Halifax Public Gardens
- Maritime Museum of the Atlantic
- Point Pleasant Park
- Lawrencetown Beach Provincial Park
- Little Rissers Beach
- Oxners Beach
- Halifax Central Library