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, 161 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

4.78 out of 5 average rating, 130 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, 201 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 bright and airy living space is highlighted by large windows that offer natural light. A hanging chair and a cozy couch provide seating, with a wooden coffee table at the center. Green plants add a touch of nature to the inviting atmosphere.

Cottage in Chester

4.95 out of 5 average rating, 147 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 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

4.8 out of 5 average rating, 141 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, 314 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, 134 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!

Superhost

Farm stay in Blockhouse

4.8 out of 5 average rating, 521 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 for winter (small $ other seasons). Optional woodfired pizza oven, charcuterie, cheesemaking class & more. *Ask for a pkg price (see below for add-ons pricing).

Guest favorite

A bright and airy open-concept living area features wooden paneling on the ceiling and large windows providing ample natural light. A dining table with white chairs sits prominently, surrounded by decorative plants, while a cozy seating area with a dark sofa invites relaxation.

Cottage in Hubbards

4.93 out of 5 average rating, 168 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

A spacious deck features a white adirondack chair, providing a view of Lunenburg Harbour and the surrounding landscape. The calm water reflects the distant green hills and various boats, while a collection of buildings with vibrant rooftops is visible in the foreground.

Loft in Lunenburg

4.88 out of 5 average rating, 199 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

A well-equipped bathroom features a walk-in shower with clear glass doors and modern fixtures. A small vanity with a mirror and wooden cabinet provides storage. Soft green and beige stripes decorate the rug, complementing the neutral tones of the walls and tile flooring.

Bungalow in Chester Basin

4.98 out of 5 average rating, 105 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 ,

Top guest favorite

A private hot tub is situated on a patio, overlooking the serene waters of the bay. Surrounding pine trees and natural landscaping frame the scene, while distant islands are visible in the background. A clear sky complements the tranquil setting.

Apartment in Prospect Bay

4.8 out of 5 average rating, 100 reviews

Beautiful ocean front couples getaway

A one bedroom self contained unit with full bathroom, kitchen, dining area, open/bright living room, with TV, internet, WiFi, & cable. Private entrance,parking, private courtyard with outdoor kitchen, beach and fire pit. A great place to relax or romantic getaway. A perfect well appointed unit perfect for two. Sit by the fire table or enjoy the ocean view.