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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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Farm stay in Blockhouse

4.8 out of 5 average rating, 461 reviews

Cottage Farm Oasis Mahone Bay- Hottub Goats Nature

May - get 3wk SPECIAL Rate! Retreat to beautiful heritage farm sanctuary nr Mahone Bay & Bridgewater. Popular with Sensea Spa. Charming studio cottage (1room) - privacy & nature, less than 1hr to Halifax. Perfect romantic getaway or solo/friend escape - unwind & recharge. BBQ, propane or wood firepit, Wifi/smartTV, boardgames, heat pump/AC. Hike, goat cuddles. *No pets. Options: hottub, wood-fired pizza oven, brekkie, charcuterie, cheesemaking class. See below for add-ons prices incl firewood.

Oct. 14 – 21

$190 CAD per night

Guest favourite

Home in Hubbards

4.96 out of 5 average rating, 191 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.

Jun. 1 – 8

$475 CAD per night

Guest favourite

Cottage in Chester

4.94 out of 5 average rating, 127 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!

Dec. 5 – 12

$429 CAD per night

Guest favourite

Guest suite in Lunenburg

4.94 out of 5 average rating, 531 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 !

Oct. 14 – 21

$217 CAD per night

Guest favourite

Cabin in Bridgewater

4.98 out of 5 average rating, 222 reviews

Wilkies Cove Boathouse

This new cottage that is inches away from the Lahave River. You can enjoy the deck , swim, fish, kayak, or just sit back on the dock and watch the Eagles and Osprey dive for fish, Seals bask in the sun on the nearby shoal. You are just minutes away from Risser's Beach, Cresent Beach and Green Bay, Hirtle's Beach where you can hike the beautiful Gaff Point ( 2 hour hike).You can also take a 10 minute drive to the famous town of Lunenburg where the Bluenose calls home port. 1 hour from Halifax.

Oct. 11 – 18

$268 CAD per night

Guest favourite

Cottage in Windsor

4.93 out of 5 average rating, 262 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.

Feb. 27 – Mar. 6

$125 CAD per night

Guest favourite

Chalet in Windsor

4.98 out of 5 average rating, 132 reviews

★ Luxury Lake Home on Falls Lake

★ 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, air conditioned, comfortably furnished & features a beautiful granite kitchen with breakfast bar, new appliances & 2 full bathrooms. It overlooks pristine Falls Lake and features a fire pit, dock, swim raft, 2 kayaks, 2 paddle boards, row boat, canoe & lots of life jackets; 20 min. from Ski Martock!

Nov. 20 – 27

$252 CAD per night

Guest favourite

Cottage in Summerville Centre

4.94 out of 5 average rating, 118 reviews

Summerville Beach Cabin

A three minute walk to Summerville's km long white sand beach and the Quarterdeck Restaurant! Warm and welcoming, this cottage boasts modern conveniences while retaining the beachy charm of a little hideaway cottage and is ideal for small families, couples, or solo adventurers. Enjoy the fire pit next to a picturesque river or take a short drive to White Point Beach Resort for surfing or golf, beautiful Carters beach, or the Keji Seaside Adjunct for a scenic hike and seal watching.

Sep. 13 – 20

$223 CAD per night

Guest favourite

Apartment in Halifax

4.82 out of 5 average rating, 216 reviews

Charming Historic apt

Built in 1894, this beautifully renovated one bedroom apt has lots of character and is equipped with all of the essentials. It is self contained with a separate entrance. Enjoy the convenience of the North End - walking distance to amazing cafes, markets and restaurants. We live upstairs and go to work early, so we ask that our guests are quiet. We do not have a driveway and street parking is difficult to find. You have to drive around the neighbourhood until you find a spot.

Sep. 17 – 24

$178 CAD per night

Guest favourite

Tiny homes in LaHave

4.98 out of 5 average rating, 245 reviews

HillTop Farm Cottage

We are offering our cottage on our little homestead located near Crescent Beach on the South Shore of Nova Scotia. This is a working homestead with chickens and cats with two operational greenhouses and a couple of large gardens. We are located about 1.5 hours outside of Halifax and within 30 minutes of historic Lunenburg and charming Mahone Bay. Come and stay with us and experience the beauty and charm of this quaint location and discover the hidden gems in the area.

Nov. 19 – 26

$153 CAD per night

Guest favourite

Cottage in Hubbards

4.94 out of 5 average rating, 142 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. 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... NS Registration RYA-2023-24-03271607054053620-8856

Feb. 24 – Mar. 3

$445 CAD per night

Guest favourite

Guest suite in Enfield

4.91 out of 5 average rating, 211 reviews

Carriage Lane

This compact one bedroom in-law suite is a comfortable place for 3 adults, or 2 adults and 2 children. It is attached to a house located in a quiet suburb situated 15 minutes from the Stanfield International Airport. and 30 minutes from the historic Bedford Halifax Dartmouth area. It is located on the route to Cape Breton, Stewiacke mastadon ridge and tidal river rafting. Tourist attractions such as Peggy's Cove and Funday tides are within easy driving range.

May 21 – 28

$100 CAD per night

Vacation rentals for every style

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Cottages

Quaint homes, peaceful surroundings

Hotels

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Popular amenities for Chester family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Loft in Dartmouth

4.92 out of 5 average rating, 227 reviews

Harbour View Loft

Aug. 29 – Sep. 5

$212 CAD per night

Guest favourite

Home in Chester Basin

4.94 out of 5 average rating, 86 reviews

The Oasis on Blueberry Lane

Sep. 14 – 21

$706 CAD per night

Guest favourite

Apartment in Prospect Bay

4.8 out of 5 average rating, 90 reviews

Beautiful ocean front couples getaway

Aug. 5 – 12

$323 CAD per night

Guest suite in Lawrencetown Beach

4.62 out of 5 average rating, 63 reviews

Lawrencetown Beachfront NEXTASEA studio apt

Oct. 20 – 27

$228 CAD per night

Cabin in Mahone Bay

5.0 out of 5 average rating, 25 reviews

Ripple Cove Cottage- An All Seasons Retreat

Dec. 12 – 19

$527 CAD per night

Guest favourite

Cabin in Three Fathom Harbour

4.94 out of 5 average rating, 68 reviews

Lawrencetown Lakefront Cottage Rental by Owner

Nov. 22 – 29

$194 CAD per night

Guest favourite

Cabin in Barss Corner

5.0 out of 5 average rating, 22 reviews

Beautiful waterfront cottage on Sherbrooke Lake

Mar. 2 – 9

$448 CAD per night

Home in Ingramport

4.92 out of 5 average rating, 64 reviews

Lakefront Cottage next to ocean beach

Sep. 11 – 18

$374 CAD per night

Family- and pet-friendly home rentals

Guest favourite

Apartment in Halifax

4.85 out of 5 average rating, 401 reviews

1 Bedroom Apt (301) in Heritage Building

Nov. 19 – 26

$160 CAD per night

Guest favourite

Home in Dartmouth

4.91 out of 5 average rating, 101 reviews

Harbour View Home

Oct. 4 – 11

$155 CAD per night

Guest favourite

Home in LaHave Island

4.77 out of 5 average rating, 123 reviews

Stunning Island Home Above Treetops Near Lunenburg

Dec. 5 – 12

$287 CAD per night

Guest favourite

Apartment in Halifax

4.89 out of 5 average rating, 186 reviews

Halifax Central - Apt /Bachelor-Back Ground Level

May 27 – Jun. 3

$398 CAD per night

Guest favourite

Bungalow in Chester Basin

5.0 out of 5 average rating, 88 reviews

Ocean Front Home Chester Basin

Jan. 11 – 18

$137 CAD per night

Guest favourite

Home in Chester Basin

4.87 out of 5 average rating, 39 reviews

Cottage in the Woods

May 29 – Jun. 5

$268 CAD per night

Guest favourite

Apartment in Halifax

4.9 out of 5 average rating, 100 reviews

Modern 1858 Apartment, w/ Music Studio & Workshop

Guest favourite

Home in Rose Bay

5.0 out of 5 average rating, 57 reviews

Ocean View - 'SeaHaven' Cottage

Apr. 22 – 29

$426 CAD per night

Family-friendly home rentals with a pool

Guest favourite

Condo in Halifax

4.87 out of 5 average rating, 354 reviews

Harbourfront Living in the Heart of Downtown

Jul. 2 – 9

$746 CAD per night

Guest favourite

Cottage in Hunts point

4.87 out of 5 average rating, 111 reviews

Relaxing Oceanfront Retreat. Private luxury

Nov. 12 – 19

$1,059 CAD per night

Cottage in Hunts Point

4.68 out of 5 average rating, 44 reviews

Oceanfront home in White Point Estates.

Nov. 29 – Dec. 6

$597 CAD per night

Home in Halifax

4.86 out of 5 average rating, 58 reviews

Luxury Home on Halifax Waterfront w/Pool & Hot Tub

Oct. 4 – 11

$1,633 CAD per night

Guest favourite

Home in Pentz

4.94 out of 5 average rating, 64 reviews

Riverhouse in Pentz

Mar. 22 – 29

$427 CAD per night

Guest favourite

Home in Nova Scotia

4.88 out of 5 average rating, 33 reviews

The Blue Cottage

Sep. 19 – 26

$326 CAD per night

Guest favourite

Home in Hubbards

4.95 out of 5 average rating, 41 reviews

Anchorage House

Mar. 6 – 13

$1,409 CAD per night

Guest favourite

Condo in Halifax

4.82 out of 5 average rating, 395 reviews

Harbourfront Home Away From Home

Oct. 2 – 9

$469 CAD 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
700 reviews
Nightly prices starting at
$123 CAD before taxes and fees

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