Family-friendly vacation rentals in Chester

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Chester

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Chalet in Windsor

4.99 out of 5 average rating, 150 reviews

Luxury Lake Home on Falls Lake with woodstove

★ Enjoy the peace & comfort of this bright 4 season luxury vacation home nestled in a private lakeside forest on Falls Lake just 60 min. from Halifax. Our rustic lake home is fully equipped, central air conditioned, comfortably furnished & features a beautiful granite kitchen with breakfast bar, new appliances & 2 full bathrooms. It overlooks pristine Falls Lake & features a fire pit, dock, swim raft, 2 canoes, 2 kayaks, 2 paddle boards, row boat & lots of life jackets; 20 min. from Ski Martock!

Guest favorite

Cottage in Windsor

4.92 out of 5 average rating, 295 reviews

Knotty Pine Cottage - cozy lakeside getaway!

Welcome to Knotty Pine Cottage - the perfect place to relax and enjoy nature. This 2-bedroom, 1 bathroom cottage has everything you need for your year-round getaway. Located in beautiful Chalet Hamlet, a private quiet cottage community that offers a relaxing retreat from the busy pace of everyday life. Beautiful Armstrong Lake is across the road, as is the community swimming area and boat launch. Knotty Pine Cottage is located 10 minutes from Martock/OnTree, and 20 minutes from Windsor.

Guest favorite

Home in Chester Basin

4.94 out of 5 average rating, 122 reviews

The Oasis on Blueberry Lane

Enjoy swimming or kayaking in our beautiful lake. Afterwards, hop in the hot tub to relax your tired muscles, then roast marshmallows over the firepit or have a game of pool. You can also curl up next to wood stove for a lazy evening in. Take a short drive to one of the several stunning beaches. Enjoy being 10 minutes from both SENSEA Nordic Spa, and Chester Village - where you'll find Chester Golf Course, a selection of restaurants, cafes, and shops. Only 30 minutes to ski Martock!

Guest favorite

Guest suite in Dartmouth

4.86 out of 5 average rating, 124 reviews

Beautiful Studio Downtown Dartmouth

Our large recently remodelled basement is where you will be staying. Enjoy all the amenities you need in a location that can't be beat. You will be located a five minute walk to Lake Banook and fifteen minute walk to downtown Dartmouth or the ferry to Halifax. Fifteen minute walk to grocery store and twenty minute drive from Halifax Airport. Our street is right on the bus route to Halifax. If you are travelling with a child under 3, they would fit in the space with you, comfortably.

Guest favorite

Tiny home in Martins River, Mahone Bay

4.93 out of 5 average rating, 229 reviews

Pirate's Roost, a tiny house in Martins River, NS.

A bright and cosy little house just off the Lighthouse Route on a quiet dead end road that curves along the river to the mouth of the bay. The property consists of grass lawns, flower gardens, surrounding woods and a river view. Enjoy our private dock and peaceful nature walks along the water or woods during all of the beautiful seasons. Hang out in the open concept downstairs. Cook a meal inside or bbq outside. Relax in front of the fire while dozing or reading a book.

Superhost

Home in Hunt's Point

4.83 out of 5 average rating, 199 reviews

Hunt's Point Beach House ( Summerville-Liverpool)

My husband Jon and I host visitors to our cozy family vacation home. Our 3 bedroom, 2 bathroom ocean view house is located in scenic Hunts Point, Nova Scotia. It sits across the street from Hunts Point public beach and a short drive to other scenic beaches. Liverpool is 10 min away for groceries; White Point Resort and Quarterdeck Grill each a 5 min drive. Relax on a large deck while listening to the ocean. We love to cook and our kitchen is fully equipped.

Superhost

Farm stay in Blockhouse

4.8 out of 5 average rating, 506 reviews

Sweetwood Farm Sweet Cottage - Hottub Goats Nature

Retreat to a beautiful heritage farm sanctuary. Popular for SenseaSpa, nr Mahone Bay/L'burg/Bwater. Charming studio cottage (1room), less than 1hr to Halifax. Perfect for touring, romantic getaway or solo/friend escape - unwind & recharge. BBQ, firepit, Wifi/smartTV, AC. *No pets - cuddle our 35 pet goats instead! Optional: Hottub, wood-fired pizza oven, brekkie, charcuterie, cheesemaking class & more. *Ask for a pkg price (see below for add-ons pricing).

Guest favorite

Cottage in Hubbards

4.93 out of 5 average rating, 163 reviews

Cleveland Beach Cottage

Beautiful Cleveland Beach Cottage overlooking the ocean in St. Margaret's Bay with white sandy beach 250 yards away and outdoor hot tub for 2! Updated, clean and bright with new flooring in main areas. Large windows in great room with full water views of picturesque St. Margarets Bay. Enjoy the inspiring sound of rolling waves, amazing sunrises and colours of sunsets are reflected on the water. Smell the ocean breeze... New STR #STR2425D7182

Guest favorite

Loft in Lunenburg

4.88 out of 5 average rating, 196 reviews

Ocean View Loft Overlooking Harbour

Explore the unique UNESCO heritage town in this bright, loft style apartment. You won't miss any of the action sitting on the large, sunny deck overlooking Lunenburg Harbour & the Bluenose II. Whether it's the comings & goings of the majestic schooners; the dory or sailboat races; the arrival of new vessels which have come from afar; or simply the daily activity of the harbour; everything happens on the Bluenose wharf.

Guest favorite

Bungalow in Chester Basin

4.99 out of 5 average rating, 103 reviews

Ocean Front Home Chester Basin

Mini Home private Quiet area with ocean view. Large Deck Everything you need dishes, pots pans, washer and dryer, dishwasher, One double bed, one queen size bed, 2 full bathroom Master Bathroom with shower, Bathroom 2 regular tub/shower. Pets are welcome if the humans are well behaved. Halifax 45 minutes, 10 minute to Chester, 15 minutes to New Ross, or Town of Mahone Bay, Lunenburg 25 minute, Airport Halifax 1 hour ,

Guest favorite

Rental unit in Indian Harbour

4.97 out of 5 average rating, 210 reviews

Driftwood Seaside Retreat

Beautiful self contained cozy apartment attached to main house near Peggy's Cove, NS. Surrounded by the ocean with stunning views from all windows. 1 bedroom with very comfortable Queen bed and quality linens, 3 piece bathroom, inviting living room, well stocked eat-in kitchen and private deck with Webber bbq. Tastefully decorated with driftwood and seascape touches. Beth and Tony look forward to hosting you!

Guest favorite

Rental unit in Downtown Halifax

4.9 out of 5 average rating, 130 reviews

Modern 1858 Apartment, w/ Music Studio & Workshop

Registered under new Airbnb rules of October 2024. STR2425A9360, valid until 31 March 2025. Stunning high-end 2014 renovation of 1858 historically registered home. Large open basement apartment with large windows, stone and brick walls, lots of closet space, full bathroom, fully equipped kitchen, and laundry. Great location, downtown, and a few metres from Halifax's award winning Central Library.