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
Flat in Prospect Bay
4.8 out of 5 average rating, 101 reviews

Beautiful ocean front couples getaway

DanielRating, 5 stars1 month 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
Flat 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.

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
Flat 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 Quinpool District
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
Home in Nova Scotia
4.9 out of 5 average rating, 42 reviews

The Blue Cottage

MarthaRating, 5 stars1 day ago
JP was very friendly and we enjoyed the animals.
Top guest favourite
Flat in The Hydrostone
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

Family-friendly home rentals with wifi

Guest favourite
Guest suite in North End
4.76 out of 5 average rating, 326 reviews

Charming In-law Suite Room - Hydrostone Market

RoumenRating, 5 stars1 week ago
NICE PLACE IN A CHARMING RESIDENTIAL AREA OF HALIFAX We had a very good time in Peter's place. Everything we needed was available there, including very friendly and helpful conversations with Peter. We recommend Peter's place for people who enjoy privacy, calm and charming residential area. There is a direct and convenient bus service to downtown (# 7A and 7B).
Guest favourite
Flat in Mahone Bay
5 out of 5 average rating, 11 reviews

Main Stay

CindyRating, 5 stars1 month ago
If you are looking to stay in Mahone Bay, this is a perfect spot! The apartment was beautiful, spotless and had lovely views over the bay. You can walk to restaurants, shops and the hosts Chris/Sandy/Kip were so responsive and helpful with any questions. We had dinner at Betty’s (recommended by hosts) and Rebecca’s and both were terrific (make sure to reserve). The shops offer some really unique things and our favourite was the Lighthouse Market (right beside our apartment) as everything is made in Nova Scotia (shop Canadian 🇨🇦 - ELBOWS UP!). We bought some really neat things to take back home to Ontario. We went hiking on the Dynamite Trail and there are lots of options for hiking. We definitely plan to be back!
Top guest favourite
Holiday home in Mount Uniacke
4.99 out of 5 average rating, 71 reviews

Lily Lakehouse - Relax & Breathe

DarshilRating, 5 stars1 month ago
We had an absolutely incredible experience here. I would recommend this airbnb to everyone! Ample space, fabulous amenities and great host. The kayaks and vast backyard and access to the lake was a game changer. Would definitely come back!
Guest favourite
Flat in North End
4.88 out of 5 average rating, 118 reviews

1 Bedroom Halifax Home with a Great Location

KaitlinRating, 5 stars2 weeks ago
Catherine's place was the perfect spot! it's very private and is a nice big walk out basement with tall ceilings and a beautiful little backyard. it was very clean and had all the amenities that we needed. The kitchenette is small, but if you plan ahead it's very workable. the location is also very convenient - close to downtown.
Guest favourite
Flat in Marriotts Cove
4.89 out of 5 average rating, 54 reviews

Sailors’ Paradise - Stevens Cove Guest Quarters

DebbieRating, 5 stars8 months ago
Thank you for a wonderful stay! It was the ideal spot for a peaceful and relaxing visit, right on the bay! Our favourite part of the day was late afternoon, sitting on the deck with a glass of wine and watching the sailboats return. The accommodation had everything we needed for a comfortable stay. We appreciated the washing machine and dryer, and the bbq - it really made us feel at home. The only thing I missed was having cable or a radio to catch up on news - but then again, sometimes it is good to disconnect from the world. We highly recommend this vacation spot to anyone looking to visit the South Shores area (Chester / Mahone Bay).
Superhost
Cottage in Hubbards
4.88 out of 5 average rating, 78 reviews

Fish Store Cottage on the ocean wharf Hubbards

MRating, 5 stars10 months ago
A truly magical place. Location is ideal to visit so many different towns, trails and excursions. However, starting the morning off on the deck watching the sunrise and then ending the day cooking on the BBQ. The house is fully equipped with every kitchen gadget needed. 3 good sized bedrooms with comfortable mattresses. There is a wonderful community feeling.
Guest favourite
Home in Brooklyn
5 out of 5 average rating, 68 reviews

The Mighty Atlantic Guest House

JonathanRating, 5 stars8 months ago
Great stay at the Atlantic for 9 adults! Beautiful home blending an historic house with modern amenities. 2.5 baths was a blessing on a busy wedding weekend. Highly recommend!
Guest favourite
Flat in North End
4.87 out of 5 average rating, 92 reviews

Family friendly 1bedroom apartment, Halifax

AaronRating, 5 stars9 months ago
We had a lovely stay with Helene. She was amazingly responsive and super helpful with whatever we could have needed. Will definitely stay again in the future!

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

  • Total rentals

    40 properties

  • Nightly prices starting at

    $103 SGD 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

  • Wifi availability

    40 properties include access to wifi

Destinations to explore

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