
Family-friendly holiday rentals in Chester
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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

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

Studio Apt at Cove Cottage Eco Oasis
Cove Cottage is a lakefront eco-retreat tucked into the woods, 45 mins from HRM. We vibe with nature. Walk the boardwalk, sit lakeside enjoying the views, feed the chickens, wander the gardens, or currently the snow banks ❄️ We are scent free & all natural with 100% cotton bedding Your stay includes a DIY Breakfast bar: Pancakes, syrup, rolled oats & oatmeal pkgs & of course coffee and tea Studio Suite is an Apartment here in our main building, more detail ⬇ TT, IG & FB: covecottageecooasis

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.

the ISLAND - A Charming Island Cottage and Bunkie
The ISLAND provides an amazing and unique escape that is truly one of a kind. This remarkable location is located only minutes off the highway and is less than an 1.5hr drive from Halifax. Enjoy the day exploring the shores and endless ocean views on land or in one of the kayaks or canoes provided. Spend the evenings with your favorite drink (and people) around the bonfire. However you decide to spend your time, we hope you enjoy your stay at this tranquil and picturesque island escape.

Cozy Cottage on South Shore. 30 min from Halifax!
A very cozy and peaceful place to base any vacation on the South Shore out of. Very close to hiking and ATV trails. No visible neighbors from the yard, lots of wildlife. Large parking areas. Interior is a mixture of new and re purposed materials. Appliances are small but functional, all the comforts of home but smaller. Double bed is incredibly comfortable. It is my home that I vacate for guests, and contains some sentimental decorations and items. RYA-2023-24-03271525339628999-1197

East Coast charm, cabin and hot tub by the river
The perfect location to explore the very popular South Shore of Nova Scotia. Close to beaches, cafes, restaurants, charming fishing villages and many other amenities. Come for a magical getaway. Tucked away in the woods along side a babbling brook. Enjoy morning coffee on the deck, BBQ your dinner overlooking the river, groove to our vintage record collection, keep toasty by the wood stove and float in the hot tub under the stars. This is a wonderful cabin experience you won't forget!

Cozy Lakefront Cottage w/ wood stove near Martock
This pet friendly, four season cottage is the perfect space to escape the city with a loved one for a weekend or for your next family vacation! Only 50 minutes from Halifax, it’s in perfect proximity between downtown Chester and Windsor. The home Includes a large eat in kitchen with sitting area, bathroom, laundry and two bedrooms on the main level and a walkout primary bedroom and large living room with wood stove on the lower level and a large walk out deck overlooking the lake.

Moss Cottage on the Lake
Moss Cottage can be your getaway only 45 minutes from Halifax and a few kilometers from the village of Chester on Nova Scotia's beautiful south shore. It's your choice to take in the many local sights, shop in towns and villages that dot the coastline, sail, play golf or stretch out on any number of beaches -- all within easy driving. Or, perhaps you'd prefer to stay put at Moss Cottage for a lovely chance at solitude and a dip in our crystal clear, spring fed lake.

Mahone Bay Ocean Retreat
Your luxury ocean getaway and private spa for two. Private beach access, keyless self check-in. On the beautiful South Shore minutes from town. Cathedral ceilings & epic views. Four seasons. Hot-tub, full spectrum infrared sauna, both indoor & outdoor rainfall showers. Indoor wet room with claw foot tub. Bbq, wireless wifi, chef’s kitchen, wine fridge, AC, wood stove, Netflix, and King size bed with premium linens. A calm, luxurious space flooded with natural light.

Ocean front HotTub Private Deck waterfront BBQ
HOOK'd 14 is your seaside sanctuary. Step into modern luxury in this open-concept unit, featuring a hot tub overlooking the sea and a waterfront deck brimming with amenities. Enjoy the comforts of home and beyond with air-conditioning, a fire pit, and more in this private community oasis. Complete with a private pier and boat launch, HOOK'd 14 invites you to experience waterfront living at its finest, just moments away from the heart of Lunenburg village.

Pleasant Street Suite
Location, location, location! This studio apartment is located in the heart of Mahone Bay. Restaurants, shops, grocery store, pharmacy, and of course the three churches are within a 5 minute walk. The space is colourful and cheery with an east coast vibe. The apartment has a well equipped kitchenette if you prefer to cook light meals yourself. There is also a dining area which could be used as a very comfortable work space. Enjoy our beautiful town!
Popular amenities for Chester family-friendly rentals
Family-friendly home rentals with a hot tub

Wilson's Coastal Club - C5

“Fox Hollow Retreat I” - Cozy, Quite and Clean

The Shore Shack

Scenic Lakefront Suite with Private Jacuzzi

Green Goose Guesthouse on Tidal Lake, Queensland

Fox Point Lake House - Luxury Lakefront Rental!

Orig.Inns - Cozy Bunkie Hideaway with Hot Tub

South Shore cottage with ocean views
Family- and pet-friendly home rentals

Waterfront cottage, private beach, LaHave River.

Fun on Falls Lake; cozy woodstove

Architecturally-designed: The Rosebay, B2 Lofts

Unique oceanfront home near Lunenburg

Welcome to the Cozy Quilt

Cozy log cabin nestled between Prospect & Shad Bay

Quarrie Cottage | Mahone Bay

The Harmony Grand at Molega Lake
Family-friendly home rentals with a pool

Half Moon Cove Retreat

Oceanside Home within the City; A Cycle Away!

North End Nest

Oceanview Luxury Estate - Magazine Perfect!

Beautiful new 6 bedroom lakehouse close to Halifax

Bright 1 BR with Lots of Sunlight & 6 Appliances

Oceanfront Cottage - Modern & Private

Waterfront Apartment in Beautiful Fall River
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $195 SGD | $192 SGD | $184 SGD | $186 SGD | $230 SGD | $275 SGD | $336 SGD | $336 SGD | $294 SGD | $317 SGD | $291 SGD | $278 SGD |
| 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 $64 SGD 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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- Family-friendly rentals Nova Scotia
- Family-friendly rentals Canada
- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Conrad's Beach
- Lawrencetown Beach Provincial Park
- Canadian Museum of Immigration at Pier 21
- Ski Martock
- Point Pleasant Park
- Halifax Public Gardens
- Maritime Museum of the Atlantic
- Halifax Central Library
- Shubie Park
- Luckett Vineyards
- Grand-Pré National Historic Site
- Fisherman's Cove
- Kejimkujik National Park & National Historic Site
- Dalhousie University
- Crystal Crescent Bch Provincial Pk
- Halifax Waterfront Boardwalk
- Peggys Cove Lighthouse
- Museum of Natural History
- Big Mushamush Lake




