
Family-friendly holiday 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.

Birch tree abode-Bunkie with dry/wet CEDAR SAUNA
Welcome to ‘Birch Tree Abode’. A unique way to unwind after a day in lunenburg county.Situated between Lunenburg and Mahone bay. Minutes from either. This bunkie’ is situated amongst the trees, with comfortable deck to enjoy the beginning/end of your adventures around the South Shore. A beautiful open plan living space, high end bathroom, all rustically finished . 400sq ft-this is slightly larger than a ‘tiny home’, however minimal space 4 storage/luggage ,also note 5.10 ceiling in bedroom area

Fox Point Lake House - Luxury Lakefront Rental!
Featured on Home Shores - Season 2, Episode 1! This one of a kind luxury lake house has plenty to offer. Gorgeous lakefront, private beach, hot tub that overlooks the lake, water views from the main floor and primary bedroom, wood fireplace and the list goes on. Other features include: - 30 mins from Halifax - Cathedral ceilings with A frame front - Built in wet bar with wine and beer fridge - Private sand beach - Salt water hot tub that comfortably sits 7 Check our IG - @foxpointlakehouse

Chester Oceanfront Luxury Villa
Welcome to Skipper Hill, where you will find this stunning villa nestled in the corner of the community, on a 178' oceanfront lot! Enjoy being 10 minutes from both SENSEA Nordic Spa, and Chester Village - where you'll find a selection of restaurants, cafes, and shops sure to please any discerning traveller. Our villa was professionally built and decorated in 2020, thoughtfully prepared for both short and long stays. You'll love the uninterrupted ocean views, countless windows capturing the ocean

FFA Close to Nordic Spa — Accepting Travel Nurses
• "Occupancy Fees or Property use taxes" is the mandatory local sales tax charged by Airbnb (HST 14%) • 3pm Checkin • 15 mins from NORDIC Spa • 10 mins from Mahone Bay • Shared laundry facilities • Free bikes provided with access to the Chester Connection Trail • A/C, cable TV, wifi & free parking on site • Cozy & comfortable with a large back deck, BBQ. Stand up shower only. • Please note this cottage has 7' ceilings (not 8') • The second bedroom is best suited for a child (more info below)

Farmstay Yurt
A simple cozy accommodation on an 30 acre off grid farm in Blockhouse. We are a walk from a large trail system where you can easily walk to the local organic cafe: Chicory Blue for a wholesome breakfast or lunch. This 20'' yurt is set right next to a flowing creek with its own modest kitchenette including small propane oven and a solar fridge. The farm is home to 1 horse, pony, 10 sheep, 2 peacocks, Angora bunnies, chickens, kunekune pigs, goats and a large greenhouse and vegetable garden.

Sleep in the clouds. 30 feet in the air with hotub
Perched high on an ocean hillside, built on 30 ft tall steel legs, the cozy quarters above are akin to an old ship’s cabin. With 360 views at 30ft up you can chart the sun and stars across the sky, set your rhythm to the ebb & flow of the tide and scout the surf from above. Greet the evenings with a cozy woodstove, sunset with drinks on the deck, moonrise with a dip in the hottub & mornings with fresh espresso. Permit yourself to depart land for a while and come stand watch at The Tower.

The Boathouse on Scotch Cove
This little boathouse sits right on Scotch Cove in East Chester, NS. Enjoy seaside views from every angle, with lovely outdoor seating and propane BBQ. The deck leads directly to the dock allowing for easy access for swimming or watercraft provided. The place is just a short walk from hiking and biking trails, with nearby lakes and sandy beaches. The indoor projector and screen make movie nights so much better! The boathouse is fully equipped for winter with a cozy woodstove.

The Oasis on Blueberry Lane
Welcome to your private lakefront escape in Chester Grant. Swim from the dock on a warm, swimmable lake, paddle at sunrise, and soak in the hot tub beneath star-filled skies. Gather around indoor and outdoor wood fires in every season, then head inside for pool tournaments and spacious, comfortable living designed for connection and relaxation. Just 10 mins to Sensea Nordic Spa and 30 mins to Ski Martock, the perfect four-season retreat for families and friends year-round.

Burns Cove Cottage. Superb home, fabulous views.
Burns Cove cottage is a spacious, fully equipped vacation home. The waterfront location makes it a prime spot to relax, view nature. It’s also a great location to bike/ hike/drive the Lighthouse Route and Rails to Trails. Lunenburg, Mahone Bay, Chester and Bridgewater have some amazing local eateries, craft breweries, local wineries and lots of shops. A quick drive to the free ferry ride gets you to the LaHave bakery, crafts, pottery, art galleries and many beaches.

Ocean Front #3 HotTub Sunset RoofTopDeck BBQ 2bath
Waterfront Cottage: Huge deck, sun sets, Private Hot Tub: 6 Person tub for 2. Panoramic Water Views: Modern Cabin: privacy and a peaceful environment. Large Deck: outdoor living space both you can take in the sun or retreat into the share. Nature Retreat with wildlife Romantic Escape: for couples, Heated floors, Shower tower, queen master, an extra guest could sleep on the couch. Super private chefs kitchen. Well equipped for all seasons.

Norse Geodesic Retreat (Freya)
Experience the epitome of relaxation and luxury at Norse Geodesic Retreat. Nestled amidst nature's embrace, our distinctive geodesic domes offer an unrivaled escape from the hustle and bustle of everyday life. Step into a world of elegance and tranquility as you gaze through floor-to-ceiling windows at the breathtaking views outside. Unwind on your private deck, where a rejuvenating soak in the hot tub awaits under the starlit sky.

Back Bay Cottage
Designed and built by architect Peter Braithwaite, the unique cottage design offers an exclusive and tranquil getaway. Accommodating up to 6 guests, this open concept, fully equipped cottage is ideal for couples, small families or outdoor enthusiasts any time of year. The airbnb is located 20 minutes outside of Halifax on six-acres with an outdoor fireplace, BBQ and stunning views that overlook Back Bay.
Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

Wilson's Coastal Club - C4

The Beach Loft: 5-bedroom

Birchwood on the Lake (with Hot Tub)

Hot Tub 2 Bed House NEW Kentville A/C Valley Views

Den of Zen

South Shore Sanctuary : Historic Church w/ Hot Tub

Scenic Lakefront Suite with Private Jacuzzi

Stunning, secluded chalet with wood fired hot tub
Family- and pet-friendly home rentals

Chester Basin Place

Waterfront cottage, private beach, LaHave River.

“Tranquility Cove” a Private Waterfront Oasis

The Beach Barn + Cedar Sauna

Unique oceanfront home near Lunenburg

Lakefront home with hot tub

Welcome to the Cozy Quilt

The Bear’s Den treehouse lodging.
Family-friendly home rentals with a pool

2-storey designer cottage - Shobac Farm Gate House

Half Moon Cove Retreat

Oceanside Home within the City; A Cycle Away!

North End Nest

Beautiful new 6 bedroom lakehouse close to Halifax

Oceanfront Cottage - Modern & Private

Waterfront Apartment in Beautiful Fall River

Salty SeaScape 4 Bed OCEAN-VIEW Home with SWIM SPA
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £114 | £112 | £107 | £109 | £134 | £160 | £196 | £196 | £171 | £185 | £170 | £162 |
| Avg. temp | -6°C | -6°C | -2°C | 4°C | 10°C | 14°C | 17°C | 17°C | 14°C | 9°C | 4°C | -2°C |
Quick stats about holiday rentals that are family-friendly in Chester

Total holiday rentals
Explore 40 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at £37 per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
40 of Chester holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chester rentals

4.9 Average rating
Chester stays are highly rated by guests – averaging 4.9 out of 5!
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- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Conrad's Beach
- Lawrencetown Beach Provincial Park
- Ski Martock
- Canadian Museum of Immigration at Pier 21
- Point Pleasant Park
- Halifax Public Gardens
- Maritime Museum of the Atlantic
- Halifax Central Library
- Dalhousie University
- Luckett Vineyards
- Kejimkujik National Park & National Historic Site
- Halifax Waterfront Boardwalk
- Fisherman's Cove
- Crystal Crescent Bch Provincial Pk
- Shubie Park
- Grand-Pré National Historic Site
- Museum of Natural History
- Big Mushamush Lake
- Long Lake Provincial Park




