Chester Islands Holidays from £582

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Your Chester Islands Holiday

Prepare to experience Chester Islands on your own terms with a custom Chester Islands holiday package! Discovering the charms of this interesting city is made simpler with a base in a neighbourhood such as Garden Lots, which is great for watersports, among other things. Make your trip to Chester Islands even more fulfilling by going sightseeing. Oak Island, Tancook Island and Chester Golf Club are among the leading attractions worth exploring. Whatever your travel plans or budget, putting together the ultimate tailored Chester Islands holiday is a breeze with Expedia.

Top Chester Islands Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
South West Mermaid Inn

South West Mermaid Inn

2.5 out of 5
per person
18 Sept - 25 Sept
found 1 day ago
Return direct flight included
London (LON) to Halifax (YHZ)
8.2/10 Very Good! (657 reviews)
The Mermaide staff was kind and helpful. Love your idea of making simple breakfasts, made to order. Thank you! The doe and her fawns, wildlife on the side yard was enjoyable this morning. Nice large rooms, comfy beds, clean. Easy access to The CAT Ferry! We will be back.

Reviewed on 4 Aug 2025

Lux Exec Home HFX Waterfront Pool Hot Tub

Lux Exec Home HFX Waterfront Pool Hot Tub

4.5 out of 5
Save 100% on your flight
per person
13 Sept - 20 Sept
found 17 hours ago
Return direct flight included
London (LON) to Halifax (YHZ)
10/10 Exceptional! (4 reviews)
Our stay was fabulous! The ho

Reviewed on 25 Jul 2025

The Barrington Hotel

The Barrington Hotel

3.5 out of 5
Downtown Halifax
per person
18 Sept - 25 Sept
found 1 day ago
Return direct flight included
London (LON) to Halifax (YHZ)
7.8/10 Good! (4,287 reviews)
We booked this hotel for a two night stay during Buskerfest. Staff were very helpful and the site was in a perfect location. I didn't have a great view but if that was the worst thing, I was very happy

Reviewed on 4 Aug 2025

Surfside Inn

Surfside Inn

3 out of 5
per person
18 Sept - 25 Sept
found 1 day ago
Return direct flight included
London (LON) to Halifax (YHZ)
8.8/10 Excellent! (317 reviews)
It’s just awesome, just book it, you’ll thank yourself. Cheers!

Reviewed on 31 Jul 2025

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
per person
7 Sept - 13 Sept
found 24 hours ago
Return flight included
Edinburgh (EDI) to Halifax (YHZ)
9.2/10 Wonderful! (1,964 reviews)
It is OK. This hotel is not new and some areas could be renovated. The pillows are terrible.

Reviewed on 3 Aug 2025

Chester Islands Essential Information

Language
English
Currency
Canadian dollars
Top Sights
Bayswater Beach Provincial Park, Chester Playhouse and Lordly House Museum

Top hotels in Chester Islands

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 £122 per night from 13 Aug to 14 Aug
£122
13 Aug - 14 Aug
includes taxes & fees
8/10 Very Good! (744 reviews)
"Outstanding and helpful service staff and front desk help that went out of their way to be helpful."

Reviewed on 30 Jul 2025

Travelodge by Wyndham Bridgewater
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 £133 per night from 8 Aug to 9 Aug
£133
8 Aug - 9 Aug
includes taxes & fees
7.6/10 Good! (1,000 reviews)
"Good for our short stay while travelling."

Reviewed on 30 Jul 2025

Days Inn & Conference Center by Wyndham Bridgewater
Miller House By the Bay

Miller House By the Bay

2 out of 5
624 Main street, mahone bay, NS
The price is £96 per night from 3 Sept to 4 Sept
£96
3 Sept - 4 Sept
includes taxes & fees
9.6/10 Exceptional! (40 reviews)
"Beautiful loved everything"

Reviewed on 3 Aug 2025

Miller House By the Bay
See all 324 properties in Chester Islands
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Chester Islands travel package cost?
From as little as £582. Yes, you read that correctly. Our Chester Islands travel packages are a simple way to make your dollar go further. Bundle your preferred hotels, flights and rental car and get out and see this destination your way.
If I'm not able to travel, can I cancel my Chester Islands travel package?
It's impossible to predict what the future holds, so it's comforting to know that you can change or cancel your Chester Islands travel package. If you booked in the last 24 hours, you may be eligible for a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for further details.
How do I get a cheap travel package to Chester Islands?
Just think of all the thrilling things you could do in Chester Islands with a pile of extra cash in your pocket. Watch your savings stack up when you bundle your flights, hotels and extras into a Chester Islands travel package. You have loads of choice with Expedia too. In fact, you can take your pick of over 550 air carriers and 1,000,000 hotels across the globe. Whether you're heading off with the family or travelling on your own, organising a trip to Chester Islands is better with a package.
Does Expedia offer Book Now, Pay Later Chester Islands holidays?
We certainly do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply choose the payment plan that works for you during checkout and take the stress out of budgeting for your trip. Remember to bundle your flights, hotel and car hire with Expedia to get the biggest bang for your travel buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna has easy monthly payment plans that fit all budgets, so you can have that well-deserved holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your holiday over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan with Klarna.

Where should I stay in Chester Islands?
If you plan to check out Chester Golf Club, give commuting a miss and find a place to stay nearby. It's one of the most popular attractions in the area.
What are the top hotels in Chester Islands?
Compass Cottage At Deep Cove and Modern Oceanview Holiday Living In Deep Cove are a couple of the most well-known properties in Chester Islands. Why not look up the amenities and facilities at each and then decide?
How far in advance should I book my Chester Islands holiday?
While prices fluctuate, we generally recommend reserving your seat as soon as possible. Many international fares can be compared on Expedia up to a year in advance. If circumstances have left you booking late, you might still be in luck. Low prices to Chester Islands sometimes occur only weeks before departure.
What does an Expedia Chester Islands travel package include?
Much of that is up to you. You can pick from a variety of Chester Islands bundles, such as a flight, hotel and rental car. You can also book a flight with a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your perfect Chester Islands holiday looks like, get set to save!
What should I know before booking a Chester Islands travel package?
Bundling your bookings into a Chester Islands travel package is the easiest way to organise your trip. Not only that, you'll save just for combining your hotels, flights and car rentals. Once you've booked, why not add on an activity or a tour?
Can I choose my airline with a Chester Islands Expedia travel package?
Expedia offers access to more than 550 partner airlines globally, so you certainly can. Simply pick your preferred carrier and put together your ideal Chester Islands escape.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.