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Family-friendly holiday rentals in Chester

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Chester family-friendly rentals

Family-friendly home rentals with a hot tub

Cottage in Chester
5 out of 5 average rating, 14 reviews

Quiet Oceanfront Escape with Hot Tub :)

Lee-AnneRating, 5 stars36 months ago
Such a beautiful AirBnB. It was perfect for our family of 6 adults and 1 infant. Spacious and wonderful views. The kitchen was perfect for preparing meals. Lots of outdoor sitting areas, and we enjoyed the hot tub, outdoor fireplace and canoeing. A great location for exploring Lunenburg, Mahone Bay, and several beaches. Melissa was a wonderful host 😊. You won’t regret staying at Three Sheep’s to the Wind.
Home in Ingramport
4.91 out of 5 average rating, 66 reviews

Lakefront Cottage next to ocean beach

RonaldRating, 5 stars9 months ago
We had the pleasure to stay for the month of August. Great location overlooking a lake, just a short walk to a small quiet beach on the ocean. An old railway track converted to biking/walking path close by. Close to groceries and restaurants. Great location for day trips to Peggy’s cove/Halifax boardwalk/many parks and beaches. The home had everything you need. Just bring your swim trunks and spirit of adventure. We highly recommend a stay at this lovely spot.
Home in Black Point
4.48 out of 5 average rating, 113 reviews

Pet-friendly seaside escape minutes from the beach

RaymondRating, 5 stars2 months ago
Had a great stay.
Cabin in Barss Corner
5 out of 5 average rating, 23 reviews

Beautiful waterfront cottage on Sherbrooke Lake

DavidRating, 5 stars21 months ago
Our second summer stay was just as wonderful as the first. More familiar this time, so the whole family felt right at home. Chris was once again very warm and welcoming in his communications. Look forward to our third stay next year if we can be so fortunate.
Top Guest favourite
Apartment in Prospect Bay
4.8 out of 5 average rating, 101 reviews

Beautiful ocean front couples getaway

DanielRating, 5 stars4 weeks ago
We had such a wonderful stay. The property is so beautifully landscaped by Bruce and Leesa. You can see the love and care they put into it. The inside was no exception. It felt warm and inviting. Leesa and Bruce are wonderful people. Very friendly and put us at ease right away. Really really nice couple. Don't think twice about booking this place. You will not be disappointed. We will be coming back and will book Leesa and Bruce's place without a question. Thanks for making us feel so welcomed.
Superhost
Farm stay in Blockhouse
4.81 out of 5 average rating, 526 reviews

Sweetwood Farm Sweet Cottage - Hottub Goats Nature

NatalieRating, 5 stars1 month ago
We rented the tent and cabin as a group of four and had a lovely stay- the cabin was a good place to warm up in May and the tent is well equipped with a full bed, lighting, battery pack. The hot tub was a great place to unwind. Loved seeing the goats, guinea fowl, a bunny, and pups on the property and Heather was a great host!
Cabin in Mahone Bay
5 out of 5 average rating, 28 reviews

Ripple Cove Cottage- An All Seasons Retreat

HaileyRating, 5 stars10 months ago
We had an amazing stay at Beth’s place!! Exceeded expectations, you can tell they put a lot of thought in making sure you have everything you need during your stay.
Superhost
Apartment in Liverpool
4.7 out of 5 average rating, 27 reviews

Downtown Liverpool - 3rd flr loft Jacuzzi for 2

LanvinRating, 5 stars2 months ago
Super comfortable and would definitely stay here again!

Family- and pet-friendly home rentals

Superhost
Cottage in Prospect
4.68 out of 5 average rating, 31 reviews

Idyllic Ocean Front Nova Scotia Cottage

MelanieRating, 5 stars13 months ago
Most of what I'm saying is echoing what other Guests have said - it's all still true for 2024: Morry is great to work with, cottage is clean and well-equipped,  the views here are wonderful, beds are comfy and the layout worked well for us with the two main floor bedrooms on opposite sides.  The kitchen is a good size and the two full bathrooms are like new. There's a great hike trailhead a stone's throw away and, if you haven't already, you will fall in love with Prospect, NS!!
Superhost
Apartment in North End
4.64 out of 5 average rating, 104 reviews

Terrific Flat in Central Halifax

JessicaRating, 5 stars9 months ago
This place was just what we needed for our stay in Halifax. We were within walking distance of local restaurants and a cycle shop where we could rent bikes. The inside was cosy, clean, and really made you feel welcome. Andrea was responsive and a lovely host! Would definitely recommend. :)
Guest favourite
Home in Rose Bay
5 out of 5 average rating, 64 reviews

Ocean View - 'SeaHaven' Cottage

MadelineRating, 5 stars1 week ago
Catherine's place was excellent and she is a great host! She was very responsive and helpful before, during and after booking. She happily accomodated our special requests. Her place is very thoughtfully designed and stocked with everything you could need (better than any other air bnb I've been to!). Lots of nice personal and local touches as well. It is located in a great area - quiet, beautiful beach, and awesome coastal hike. You will not be disappointed! Thank you, Catherine!
Superhost
Cottage in Pleasantville

NESTOR'S POINT Riverfront Cottage - Lighthouse Motel & Cottages

JustinRating, 5 stars97 months ago
We had a great stay in this quaint coastal town of Conquerall Bank along the LaHave River at this cottage. The space provided was ample and the view from the rooms was amazing. We felt very welcomed by Marc and his pup Austin the first day. He told us about many things to do in the area and we highly recommend the Lahave Bakery a short drive away for breakfast. The cottage is very centrally located along Nova Scotias South Shore and was a great relaxing midpoint for our trip to Cape Breton. We were able to explore the area and ended up at Cresent beach around dusk and it was absolutely stunning. Highly recommend this host and property. (note: The cottage is part of the Lighthouse Motel Properties but is secluded and detached from any other guests - all very well maintained and a pleasure to stay at.)
Guest favourite
Home in Halifax
4.88 out of 5 average rating, 73 reviews

Cozy Inn

JennaRating, 5 stars1 month ago
We had an incredible trip at Candace's place. The home was stunning and was perfect for our group of 6. If you have the opportunity to book your trip to Halifax here, I would definitely recommend!
Top Guest favourite
Apartment in North End
4.93 out of 5 average rating, 120 reviews

Historic Hydrostone flat

NatalieRating, 5 stars1 week ago
One of my favourite Air B&B’s to date! Angela was such a thoughtful host and all of her recommendations were incredible (Bar Kismet, The Narrows, parks, breweries, etc). We had our pup and it was the ideal place, especially for wanting to get around mainly on foot. LOVELY neighborhood. We can’t wait to come back!
Top Guest favourite
Guest suite in Dartmouth
4.92 out of 5 average rating, 196 reviews

Harbour View Home

LisaRating, 5 stars1 week ago
Great location and lovely home
Guest favourite
Cottage in Queens County
4.93 out of 5 average rating, 114 reviews

Lakefront Cottage on Annis Lake

StephenRating, 5 stars1 week ago
Wonderful cottage and location. Everything needed was in the cottage.

Family-friendly home rentals with a pool

Guest favourite
Cottage in Hunts point
4.89 out of 5 average rating, 122 reviews

Relaxing Oceanfront Retreat- private luxury

CheraRating, 5 stars4 months ago
Stayed here for the second time, beautiful spot even in the dead of winter!
Top Guest favourite
Home in Nova Scotia
4.9 out of 5 average rating, 41 reviews

The Blue Cottage

Vincent-GuillaumeRating, 5 stars10 months ago
PAM & J.P were extraordinary. We were delighted with our stay and fell in love with Nova Scotia. The animals were an unexpected extra. Gustave is going to miss Maple a lot. Small comment WHICH IS NOT A CRITICISM. The refrigerator is not very big, so don't do too much grocery shopping at once. We arrived with too many things and not everything fit. But again, that's okay. There's a grocery store not far away. It's very easy. Just don't plan too far ahead if you have a big family like mine. The pool is amazing!!!!! Close to lots of beautiful beaches. We had a great time with the family!!!
Top Guest favourite
Home in Pentz
4.94 out of 5 average rating, 70 reviews

Riverhouse in Pentz

FredRating, 5 stars9 months ago
Fantastic hosts. Dream heritage property with total privacy and a heated pool in a park like setting; we booked that property pretty much every year for the last seven years. Rob and Barb are constantly improving the property, there is always something new to discover, whether it's a new appliance, or a brand new landscaped river frontage inviting you to sit and watch river and ocean life whilst sipping a glass of tasty red provided with the welcome basket. We enjoyed eating out at the Lunenburg restaurants, as much as we enjoyed cooking a delicious meal at their place, which is fully equipped, one can easily cook up a gourmet meal. Golden! And we shall return!! Greetings from Port Lorne, NS, Conny and Fred.
Superhost
Apartment in Downtown Halifax

Luxury Waterfront Living

CynthiaRating, 5 stars1 month ago
Great stay! The place is exactly as described and the pictures show. You can’t do better for location! You can walk anywhere downtown and have so many new restaurants just below the condo. There is ample space for everyone and the kitchen is well stocked with pots and pans for cooking at home. Chris was a fantastic host, he answered all my questions promptly and checked in as well. I will definitely come back and wouldn’t hesitate to use Chris to help find me a space.

Quick stats about holiday rentals that are family-friendly in Chester

  • Total rentals

    40 properties

  • Nightly prices starting at

    $123 AUD before taxes and fees

  • Total number of reviews

    910 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 properties include access to Wi-Fi

Destinations to explore

  1. Airbnb
  2. Canada
  3. Nova Scotia
  4. Chester
  5. Family-friendly rentals