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Family-friendly vacation 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.

Superhost
Farm stay in Blockhouse
Cottage Farm Oasis Mahone Bay- Hottub Goats Nature
Retreat to this beautiful 1760s heritage farm sanctuary nr Mahone Bay & Bridgewater. Charming studio cottage with privacy & nature on 75 acres-no neighbours, under 1hr to Halifax. Perfect romantic getaway or solo/friend escape to unwind & recharge. Hottub under the stars, BBQ, make pizza, firepit, Wifi/smartTV, boardgames, heat pump/AC, hike, goat cuddles. No pets. Optional: hottub, wood-fired pizza oven, brekkie, charcuterie, cheesemaking class. See below for $ optional add-ons like hottub.
May 13 – 20
$100 per night
Guest favorite
Cottage in Chester
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!
Apr 15 – 22
$221 per night
Guest favorite
Cottage in Windsor
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.
Nov 20 – 27
$81 per night

Popular amenities for Chester family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Loft in Dartmouth
Harbour View Loft
Mar 5 – 12
$106 per night
Guest favorite
Home in Chester Basin
The Oasis on Blueberry Lane
Nov 6 – 13
$292 per night
Guest favorite
Apartment in Prospect Bay
Beautiful ocean front couples getaway
Feb 11 – 18
$167 per night
Superhost
Guest suite in Lawrencetown Beach
Lawrencetown Beachfront NEXTASEA studio apt
Sep 15 – 22
$148 per night
Guest favorite
Cabin in Three Fathom Harbour
Lawrencetown Lakefront Cottage Rental by Owner
Dec 24 – 31
$111 per night
Guest favorite
Cabin in Barss Corner
Beautiful waterfront cottage on Sherbrooke Lake
Oct 6 – 13
$215 per night
Guest favorite
Home in Ingramport
Lakefront Cottage next to ocean beach
Oct 14 – 21
$179 per night
Home in Black Point
Pet-friendly seaside escape minutes from the beach
Dec 14 – 21
$144 per night
Guest favorite
Guest suite in East Lawrencetown
Lawrencetown Beachfront SEARENITY Studio Apt.
Aug 26 – Sep 2
$200 per night
Superhost
Guest suite in Lawrencetown Beach
Lawrencetown Beachfront TRANQUILITY Studio Apt
Oct 8 – 15
$200 per night

Family- and pet-friendly home rentals

Guest favorite
Apartment in Halifax
1 Bedroom Apt (301) in Heritage Building
Nov 26 – Dec 3
$97 per night
Guest favorite
Guesthouse in Upper LaHave
Super Special Captain's Quarters
Dec 8 – 15
$64 per night
Guest favorite
Chalet in Windsor
★ Luxury Lake Home on Falls Lake
Jun 6 – 13
$370 per night
Guest favorite
Home in Lunenburg
Stunning Island Home Above Treetops Near Lunenburg
May 12 – 19
$182 per night
Guest favorite
Home in Dartmouth
Harbour View Home
Aug 9 – 16
$128 per night
Guest favorite
Apartment in Halifax
Halifax Central - Apt /Bachelor-Back Ground Level
Oct 29 – Nov 5
$296 per night
Guest favorite
Bungalow in Chester Basin
Ocean Front Home Chester Basin
Nov 4 – 11
$79 per night
Guest favorite
Home in Chester Basin
Cottage in the Woods
Sep 12 – 19
$208 per night
Guest favorite
Home in Rose Bay
Ocean View - 'SeaHaven' Cottage
Feb 17 – 24
$226 per night
Superhost
Home in Chester
Family Home In the Heart of the Village of Chester
Sep 15 – 22
$538 per night
Guest favorite
Apartment in Halifax
Modern 1858 Apartment, w/ Music Studio & Workshop
Apr 27 – May 4
$97 per night
Guest favorite
Cottage in Leminster
Cozy Lakefront Cottage
Sep 1 – 8
$158 per night

Family-friendly home rentals with a pool

Guest favorite
Condo in Halifax
Harbourfront Home Away From Home
Oct 8 – 15
$253 per night
Guest favorite
Home in Halifax
Luxury Home on Halifax Waterfront w/Pool & Hot Tub
Apr 5 – 12
$539 per night
Guest favorite
Home in Pentz
Riverhouse in Pentz
Jan 6 – 13
$259 per night
Guest favorite
Home in Nova Scotia
The Blue Cottage
Sep 25 – Oct 2
$168 per night
Guest favorite
Home in Hubbards
Anchorage House
Jan 27 – Feb 3
$916 per night
Guest favorite
Condo in Halifax
Harbourfront Living in the Heart of Downtown
Jul 5 – 12
$408 per night

Quick stats about vacation rentals that are family-friendly in Chester

Total rentals

40 properties

Wifi availability

40 properties include access to wifi

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Total number of reviews

670 reviews

Nightly prices starting at

$90 before taxes and fees

Destinations to explore

  1. Airbnb
  2. Canada
  3. Nova Scotia
  4. Chester
  5. Family-friendly rentals