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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Top guest favorite

A spacious wooden deck extends from the cottage, featuring a seating area with four chairs, a table, and a barbecue grill. Decorative lights are strung overhead, and a red hummingbird feeder hangs prominently. The cottage exterior showcases shingled siding and large windows, surrounded by greenery.

Chalet in Windsor

4.99 out of 5 average rating, 166 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

A spacious, two-story green house is situated on a raised driveway, with multiple large windows reflecting the evening light. Two decks with glass panels extend from the upper level, providing expansive views. A parked car is seen in the foreground, emphasizing the car-accessible location.

Home in LaHave Island

4.79 out of 5 average rating, 131 reviews

Stunning Island Home Above Treetops Near Lunenburg

SkyView on LaHave Island is car-accessible, built on the highest point of a gorgeous island like a castle on a hill. A 2-story atrium, multiple large windows and skylights reveal spectacular 360-degree views of picturesque coves, a sprawling bay and the vast Atlantic. Enjoy lounging outside on 3 decks with glass panels. High-speed Internet. 5 mins from Crescent Beach swimming, 7 mins from mainland activities on Lighthouse Route, 40 mins to Lunenburg. See our video on Youtube. A phenomenal spot!

Guest favorite

A charming, historic house is nestled on a hill, surrounded by vibrant flowers and greenery. The exterior showcases a blend of gray shingles and natural wood, with inviting porches that enhance its appeal. The sky above is bright with scattered clouds, adding to the home's radiant character.

Home in Hubbards

4.96 out of 5 average rating, 202 reviews

Charming Ocean Retreat

Perched on a hill overlooking the Aspotogan Cove, this lovingly restored 150-year-old family home offers everything you might need for a relaxing peaceful retreat. The backyard opens onto four acres of trails - perfect for mountain biking and hiking - and Bayswater Beach, one of the exquisite beaches on the South Shore, is only five minutes away. The beautifully appointed chef’s kitchen invites culinary play, and an extensive collection of games, books and movies will keep you well entertained.

Guest favorite

A charming seaside cottage is framed by lush greenery, featuring a red exterior with white trim. Large windows invite natural light into the living spaces. A stone wall with vibrant flowers forms an inviting entryway to the outdoor seating area, perfect for enjoying the views.

Cottage in Chester

4.95 out of 5 average rating, 150 reviews

Scotch Cove Retreat

Scotch Cove Retreat is our beautiful seaside cottage on the south shore of Nova Scotia in Mahone Bay. It has tons of spaces, gorgeous ocean views, "pool hall", artist's studio, and private dock on Scotch Cove only minutes away from hiking trails and the sweet town of Chester. It's perfect for a relaxing time with family and close friends. (Gatherings are now limited to 16 by Airbnb.) We've put a lot of work into this space and think it has a lot of heart and character. We hope you like it too!

Guest favorite

A rustic kitchenette is featured, including a farmhouse sink on a wooden counter. A small refrigerator is positioned beneath the counter, while open shelving displays decorative items and plants. The separate entrance emphasizes a natural wood door and an inviting atmosphere.

Guest suite in Lunenburg

4.93 out of 5 average rating, 597 reviews

The Cosy Red Roof

situated between Mahone Bay/ Lunenburg! (4 min drive to Lun,7min drive to M.Bay) Step into the private entrance,you are welcomed to warm ,rustic decor to enjoy your coffee/breakfast. Private bathroom (toilet/shower) beautifully finished with chrome fixtures finish the downstairs. Upstairs,large bedroom,(queen bed)lazyboy sofa,tv ,with views of the woodland garden! (There is no ‘outside’ space for guests at this time) Heaps of character, this is an ideal setting to relax after time exploring !

Guest favorite

A view of the waterfront is depicted, showcasing sailboats gently bobbing in the water. Flags representing different regions flutter along the docks, while greenery rises in the background, adding to the scenic coastal landscape.

Apartment in Lunenburg

4.81 out of 5 average rating, 146 reviews

Romantic Waterfront Retreat in Downtown Lunenburg

Quiet and Smoke-free Accommodations. We are located In the most prized location in Lunenburg, right on the waterfront street. It does not get any better! A stones throw away from the famous ship, the Bluenose 2 and adjacent to the Fisheries Museum and the famous Lunenburg Wharf. This bright airy apartment is available for your visit to the south shore. The skylights make it the perfect space to lay back and look at the stars. Please note we do not accept pets due to severe host allergies.

Guest favorite

The cottage exterior features warm wooden siding and a covered porch with four Adirondack chairs. Surrounding trees enhance the natural setting, while a gravel path leads to the entrance. A large rock is positioned in the foreground, complementing the peaceful landscape.

Cottage in Windsor

4.92 out of 5 average rating, 322 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.

Top guest favorite

The serene lake is bordered by trees and reflects a clear blue sky. A dock with two blue chairs extends into the water, and a floating device is visible nearby. The calm surface of the lake enhances the peaceful ambiance.

Home in Chester Basin

4.95 out of 5 average rating, 141 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

The oceanfront chalet is positioned on a natural slope surrounded by greenery and rock formations. Large windows allow for abundant natural light, enhancing the view of the landscape. A wooden deck leads toward the water, creating an inviting connection with nature.

Chalet in West Pennant

4.85 out of 5 average rating, 142 reviews

Stunning Oceanfront near Halifax

This bright oceanfront chalet/cabin is secluded, quiet and all about nature, 20 minutes from Halifax. There are 2 bedrooms, 2 bathrooms, 2 floors with a deck right on the ocean. The chabet is open concept, modern, and finished with hardwood floors, copper accents and all the basic comforts. The location makes it ideal for hiking, yoga, relaxing and oceanfront living. The house is 1300 ft2. There is a heat pump for heating and cooling, the woodstove is not for guest use.

Superhost

The cozy studio cottage features a spacious bed adorned with a textured blanket. Natural wood paneling and high ceilings create an inviting ambiance, while soft light is provided by bedside lamps. A welcoming art piece enhances the serene atmosphere, and a window offers a view of the outdoors.

Farm stay in Blockhouse

4.81 out of 5 average rating, 528 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! Comp Hottub. Optional woodfired pizza oven, charcuterie, cheesemaking class & more. *If the chalet is booked, our gorgeous glamping tent with hottub may be available!

Guest favorite

A spacious outdoor deck is furnished with comfortable blue seating arranged around a large table. Lush greenery and trees are visible in the backdrop, while an inviting view of the water is framed by large windows in the cottage behind. The atmosphere is relaxed and welcoming.

Cottage in Hubbards

4.92 out of 5 average rating, 175 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 and newly renovated bath 2025!. 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

The kitchen features wooden cabinets and granite countertops, with essential appliances including a refrigerator, stove, and microwave. A coffee maker is visible on the counter. The warm wood flooring adds to the inviting feel of this functional space.

Bungalow in Chester Basin

4.98 out of 5 average rating, 106 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 ,