Book Holiday Homes in Chester

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chester

Unwind, Explore and Reconnect at Knotting Hill

Unwind, Explore and Reconnect at Knotting Hill

Mahone Bay
Book a stay at this family-friendly vacation home in Maders Cove. Enjoy free WiFi, a garden, and tennis courts. Popular attractions For The Birds Nature Shop ...
Unwind, Explore and Reconnect at Knotting Hill
Relax on the South Shore, steps from 2 beaches, ocean views & hot tub.

Relax on the South Shore, steps from 2 beaches, ocean views & hot tub.

East River Point
Book a stay at this family-friendly vacation home in East River Point. Enjoy free WiFi, a garden, and patios. Popular attractions Meisners Beach and East River ...
Relax on the South Shore, steps from 2 beaches, ocean views & hot tub.
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Hubbards
The price is NZ$489 per night from 15 Apr to 16 Apr
NZ$489
includes taxes & fees
15 Apr - 16 Apr
Book a stay at this beach vacation home in Northwest Cove. Enjoy a beach locale, a garden, and patios. Popular attractions Southwest Cove Lake and Northwest ...
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
Save an average of 15% on thousands of hotels when you're signed in
Cozy Cape Located In The Beautiful Seaside Town of Mahone  Bay

Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay

Mahone Bay
Stay at this vacation home in Mahone Bay. Enjoy air conditioning. Popular attractions For The Birds Nature Shop and The Moorings Gallery are located nearby.
Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay
Ocean front cottage in the heart of Hubbards.

Ocean front cottage in the heart of Hubbards.

Hubbards
Stay at this vacation home in Fox Point. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Shore Club Dance Hall and Hubbards Farmer's ...
Ocean front cottage in the heart of Hubbards.
Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area

Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area

Indian Harbour
Stay at this vacation home in Indian Harbour. Enjoy free WiFi, a garden, and patios. Popular attractions Indian Harbour Lighthouse and DeGarthe Gallery are located ...
Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area
Unique Ocean View Hilltop Retreat

Unique Ocean View Hilltop Retreat

Lunenburg
Book a stay at this family-friendly vacation home in First South. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Halifax and Southwestern ...
Unique Ocean View Hilltop Retreat
Modern three bedroom with Panoramic Oceanview

Modern three bedroom with Panoramic Oceanview

Hubbards
Stay at this vacation home in Northwest Cove. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Horse Island and Southwest Cove Lake are ...
Modern three bedroom with Panoramic Oceanview
Oceanfront 3-Bedroom Captain's House

Oceanfront 3-Bedroom Captain's House

Rose Bay
Book a stay at this family-friendly vacation home in Feltzen South. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Ovens Natural ...
Oceanfront 3-Bedroom Captain's House
Don't see what you're looking for?
See all available properties in Chester
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Chester Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chester vacation homes are the perfect way for you to wing it.

Holiday houses in Chester let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chester in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chester adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chester with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chester vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chester Holiday Homes essential information

Accommodation
64 Holiday Homes
Lowest Price
NZ$188
Highest Price
NZ$489
Popular accommodation
Unwind, Explore and Reconnect at Knotting Hill, Relax on the South Shore, steps from 2 beaches, ocean views & hot tub., Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia, Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay, Ocean front cottage in the heart of Hubbards., Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area, Unique Ocean View Hilltop Retreat, Modern three bedroom with Panoramic Oceanview , Oceanfront 3-Bedroom Captain's House

Top trending hotels in Chester

Family Home In the Heart of the Village of Chester

Family Home In the Heart of the Village of Chester

Chester
Stay at this vacation home in Chester. Enjoy free WiFi, a garden, and balconies. Popular attractions Tancook Island and St. Stephen's Church are located ...
Family Home In the Heart of the Village of Chester
Best Western Plus Bridgewater Hotel & Convention Centre

Best Western Plus Bridgewater Hotel & Convention Centre

3.5 out of 5
527 Highway 10 Exit 12, Cookville, NS
Fully refundableReserve now, pay when you stay
The price is NZ$210 per night from 13 Apr to 14 Apr
NZ$210
includes taxes & fees
13 Apr - 14 Apr
Stay at this 3.5-star business-friendly hotel in Cookville. Enjoy free breakfast, free parking, and room service. Our guests praise the helpful staff and the ...
Best Western Plus Bridgewater Hotel & Convention Centre
Smugglers Cove Inn

Smugglers Cove Inn

4 out of 5
139 Montague Street, Lunenburg, NS
Fully refundableReserve now, pay when you stay
The price is NZ$262 per night from 5 Apr to 6 Apr
NZ$262
includes taxes & fees
5 Apr - 6 Apr
Stay at this 4-star hotel in Lunenburg. Enjoy free WiFi, daily housekeeping, and a hair salon. Our guests praise the helpful staff and the clean rooms in our ...
Smugglers Cove Inn
Save an average of 15% on thousands of hotels when you're signed in
Days Inn & Conference Center by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater

2.5 out of 5
50 North Street, Hwy 103 and North Street, Bridgewater, NS
Fully refundableReserve now, pay when you stay
The price is NZ$188 per night from 4 Apr to 5 Apr
NZ$188
includes taxes & fees
4 Apr - 5 Apr
Book a stay at this business-friendly hotel in Bridgewater. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Days Inn & Conference Center by Wyndham Bridgewater
Don't see what you're looking for?
See all available properties in Chester
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.