Book Holiday Homes in Chester

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Featured Holiday Homes in Chester

Family Home In the Heart of the Village of Chester

Family Home In the Heart of the Village of Chester

Chester NS
Stay at this holiday home in Chester. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Tancook Island and Lordly House Museum are located ...
Opens in a new windowFamily Home In the Heart of the Village of Chester
Mahone Bay Hide-Away

Mahone Bay Hide-Away

Mahone Bay NS
Stay at this holiday home in Mahone Bay. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Jubilee Park and Have A Yarn are located ...
Opens in a new windowMahone Bay Hide-Away
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

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

Hubbards NS
Stay at this beach holiday home in Northwest Cove. Enjoy a beach locale, a garden and laundry facilities. Popular attractions Southwest Cove Lake and Northwest ...
Opens in a new windowPrivate Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia
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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 Nova Scotia
Stay at this holiday home in Indian Harbour. Enjoy free Wi-Fi, a garden and patios. Popular attractions Swissair Flight 111 Memorial and Indian Harbour Lighthouse ...
Opens in a new windowWhalesback Cottage, on the ocean with access to Peggys Cove Preservation Area
Wilson's Coastal Club - C1

Wilson's Coastal Club - C1

Boutiliers Point NS
The price is NZ$586 per night from 26 Dec to 27 Dec
NZ$586
26 Dec - 27 Dec
includes taxes & fees
Stay at this beach holiday home in Boutiliers Point. Enjoy free Wi-Fi, a beach locale and a sauna. Popular attractions Saint Margarets Bay Look Off Park and ...
Opens in a new windowWilson's Coastal Club - C1
Tucked away on quiet street but short walk to Mahone Bay and all its amenities.

Tucked away on quiet street but short walk to Mahone Bay and all its amenities.

Mahone Bay NS
Stay at this holiday home in Mahone Bay. Enjoy free Wi-Fi, laundry facilities and air conditioning. Popular attractions Mahone Bay Swimming Pool and Northern ...
Opens in a new windowTucked away on quiet street but short walk to Mahone Bay and all its amenities.
The Salty Cribb - Private oceanfront vacation home just minutes from Lunenburg

The Salty Cribb - Private oceanfront vacation home just minutes from Lunenburg

Rose Bay NS
Stay at this beach holiday home in Feltzen South. Enjoy a beach locale, a garden and laundry facilities. Popular attractions Ovens Natural Park and Indian Path ...
Opens in a new windowThe Salty Cribb - Private oceanfront vacation home just minutes from Lunenburg
The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

Ingramport NS
Stay at this family-friendly holiday home in Ingramport. Enjoy free Wi-Fi, private pools and breakfast (surcharge). Our guests praise the pool in their reviews. ...
Opens in a new windowThe Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views
Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg

Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg

Lunenburg NS
Stay at this holiday home in Lunenburg. Enjoy free Wi-Fi, laundry facilities and tennis courts. Popular attractions Pearl Theatre and Fisheries Museum of the ...
Opens in a new windowRemodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg
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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
74 Holiday Homes
Lowest Price
NZ$214
Highest Price
NZ$586
Popular accommodation
Family Home In the Heart of the Village of Chester, Mahone Bay Hide-Away , Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia, Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area, Wilson's Coastal Club - C1, Tucked away on quiet street but short walk to Mahone Bay and all its amenities., The Salty Cribb - Private oceanfront vacation home just minutes from Lunenburg, The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views, Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg

Top trending hotels in Chester

Travelodge by Wyndham Bridgewater

Travelodge by Wyndham Bridgewater

2 out of 5
49 North St Bridgewater NS
Fully refundableReserve now, pay when you stay
The price is NZ$219 per night from 1 Jan to 2 Jan
NZ$219
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this hotel in Bridgewater. Enjoy free breakfast, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowTravelodge by Wyndham Bridgewater
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$214 per night from 30 Dec to 31 Dec
NZ$214
30 Dec - 31 Dec
includes taxes & fees
Stay at this business-friendly hotel in Cookville. Enjoy free breakfast, free parking and room service. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowBest Western Plus Bridgewater Hotel & Convention Centre
Smugglers Cove Inn

Smugglers Cove Inn

4 out of 5
139 Montague Street Lunenburg NS
Stay at this hotel in Lunenburg. Enjoy free Wi-Fi, daily housekeeping and premium bedding. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowSmugglers Cove Inn
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Black Forest Cabins

Black Forest Cabins

3 out of 5
15 Longhill Rd Mahone Bay NS
Stay at this spa cabin in Mahone Bay. Enjoy free Wi-Fi, free parking and a full-service spa. Popular attractions Mahone Bay Swimming Pool and Have A Yarn are ...
Opens in a new windowBlack Forest Cabins
Don't see what you're looking for?
See all available properties in Chester
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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.