Chester Holidays

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Your Chester Holiday

Make organising your next getaway a breeze with a Chester holiday package. Whether it's the food scene, history or something else entirely that draws you to this destination, our packages will help you discover it all. A carefully planned itinerary is essential for your trip to Chester. Western Shore, Bayswater and Blandford are a few of the most well-known cities here. Expedia has everything you need when it comes to organising your Chester holiday. From hotels and flights, to activities and more, we're here to help you curate a travel experience like no other.

Top Chester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hearthstone Inn Boutique Hotel Halifax - Dartmouth

Hearthstone Inn Boutique Hotel Halifax - Dartmouth

3.5 out of 5
Price was £1,375, price is now £1,031 per person
£1,031
per person
12 Oct - 21 Oct
found 5 hours ago
Return flight included
London (LON) to Halifax (YHZ)
7.2/10 Good! (1,264 reviews)

Coastal Inn Halifax

Coastal Inn Halifax

3 out of 5
Price was £1,518, price is now £1,228 per person
£1,228
per person
12 Oct - 21 Oct
found 5 hours ago
Return flight included
London (LON) to Halifax (YHZ)
8.6/10 Excellent! (1,015 reviews)
Good place to stay. Lower price, free parking, close to where we were going and breakfast was included.

Reviewed on 7 Sept 2026

Seasons Inn Halifax

Seasons Inn Halifax

2.5 out of 5
Fairview
Price was £1,299, price is now £1,107 per person
£1,107
per person
12 Oct - 21 Oct
found 5 hours ago
Return flight included
London (LON) to Halifax (YHZ)
6.6/10 (1,000 reviews)
This property was not well kept. The room had carpet which was stained and sound traveled from other rooms very easily. In addition customer service was not that helpful with solving concerns.

Reviewed on 6 Sept 2026

Chateau Bedford, Trademark Collection by Wyndham

Chateau Bedford, Trademark Collection by Wyndham

4 out of 5
Birch Cove
Price was £1,640, price is now £1,402 per person
£1,402
per person
12 Oct - 21 Oct
found 5 hours ago
Return flight included
London (LON) to Halifax (YHZ)
9.2/10 Wonderful! (2,269 reviews)
Staff are friendly parking lots were spacious

Reviewed on 6 Sept 2026

Future Inns Halifax

Future Inns Halifax

3 out of 5
Clayton Park West
Price was £1,432, price is now £1,225 per person
£1,225
per person
12 Oct - 21 Oct
found 5 hours ago
Return flight included
London (LON) to Halifax (YHZ)
9.2/10 Wonderful! (2,426 reviews)
Bed where way too soft and didn't have a good night sleep, there was no attention to request for firmer bed. Not a good experience

Reviewed on 6 Sept 2026

Chester Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Stanfield Intl. Airport (YHZ)
Top Sights
Saint Margarets Bay, Bayswater Beach Provincial Park and Graves Island Provincial Park

Top hotels in Chester

Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive Western Shore NS
The price is £164 per night from 28 Sept to 29 Sept
£164
28 Sept - 29 Sept
includes taxes & fees
8.2/10 Very good! (579 reviews)
"Room was clean and updated with mini frig but no microwave. Facilities were great indoor & outdoor pools awesome for kids plus many other outdoor activities available as well. Fire pit and s’mores also a great hit. Fun spot for families!"

Reviewed on 7 Sept 2026

Oak Island Resort & Conference Centre
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

Chester NS
9.8/10 Exceptional! (44 reviews)
"As we drove up to the house, we could see the magnificent view it commanded from the deck with four different colored Adirondock chairs. When we walked into the house, the kitchen was in front of you, with two bedrooms to the left on either side of the bathroom. The owner did a great job on details, ..."

Reviewed on 29 Aug 2026

Get rates
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Future Inns Halifax

Future Inns Halifax

3 out of 5
30 Fairfax Dr Halifax NS
The price is £111 per night from 1 Oct to 2 Oct
£111
1 Oct - 2 Oct
includes taxes & fees
9.2/10 Wonderful! (2,452 reviews)
"Bed where way too soft and didn't have a good night sleep, there was no attention to request for firmer bed. Not a good experience"

Reviewed on 6 Sept 2026

Future Inns Halifax
See all 633 properties in Chester
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 travel package cost?
Our Chester packages, which begin from just £1,031, are the easiest way to save. Select your preferred hotels, flights and more to create your ideal itinerary.
If I'm not able to travel, can I cancel my Chester travel package?
We totally get that sometimes life doesn't go according to plan. If you've locked in a Chester travel package and have to amend or cancel it, we're here to help. We recommend browsing our Customer Service Portal first for information. But generally speaking, if you've taken out your package in the last 24 hours, you may be able to cancel or change your itinerary for free. If it's been longer than 24 hours, your hotel, airline or car rental company may charge a fee.
How do I get a cheap travel package to Chester?
Our Chester travel packages offer plenty of savings for the savvy wanderer. For the best deal, simply combine your flights, hotels and extras (including tours) into a budget-friendly package. But low prices are just the beginning of your next amazing adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 hotel options around the world to select from. No matter your budget, there's a travel package that's perfect for you.
Does Expedia offer Book Now, Pay Later Chester holidays?
We do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply select the payment plan best suited to your needs during checkout and take the stress out of budgeting for your next trip. Don't forget to bundle your accommodation, flights and activities with Expedia to get the biggest bang for your holiday buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that work for all budget sizes, so you can escape on that well-deserved holiday now.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip over multiple transactions.
  • Low deposit holidays: When you stumble on an amazing deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you lock in your escape.

What are the top hotels in Chester?
For properties in Fox Point with friendly service and comfy beds, you can't go past Charming 3 Bedroom Cottage Near Hubbards and Amazing Ocean - View Just Steps To Fox Point Beach. If you plan to explore Chester Basin as well, you can look forward to a solid night's sleep at 4 Bed - - Persons Holiday Rental With Cottage or A Sailors Paradise - Stevens Cove Guest Quarters.
How far in advance should I book my Chester holiday?
While not all airlines release tickets early, you can usually look up international fares on Expedia up to a year in advance. This is the time you can bag some incredible deals. If you've left everything to the last minute, you may still be in luck. Low prices occasionally appear a few weeks prior to departure.
What does an Expedia Chester travel package include?
Hotels, flights and a cool set of wheels for all your road trip adventures. Simply pick and choose your preferred bundle and get access to great discounts. Once you've made your booking, add on a few tours and activities and watch your savings grow. When it comes to crafting your Chester escape, you're in charge!
What should I know before booking a Chester travel package?
A travel package can be easier on the hip pocket than individually booking all you need for your getaway. For example, combine your flights, hotels and rental cars and save a pretty penny. Whatever type of holiday you have in mind, there's bound to be a package within your budget.
Can I choose my airline with a Chester Expedia travel package?
You can, and with more than 550 airlines to pick from throughout the world, you're spoiled for choice. Have a look through the available options and see which airline best suits your needs and budget.

Stay near popular Chester attractions

Bayswater Beach Provincial Park

9.0/10 (26 reviews)
If a restful holiday is part of your travel plans, Bayswater Beach Provincial Park might be the perfect place to visit during your trip to Bayswater. Make some time to visit the monuments while you're in the area.
See properties

What to do in Chester

Halifax Small Group Peggy’s Cove Driving Tour

Halifax Small Group Peggy’s Cove Driving Tour

£36
per adult
96% of travellers recommend
Halifax Small Group Peggy’s Cove Driving Tour
Half-Day Small-Group Tour of Nova Scotia's South Shore

Half-Day Small-Group Tour of Nova Scotia's South Shore

£88
per adult
100% of travellers recommend
Half-Day Small-Group Tour of Nova Scotia's South Shore
Peggys Cove Sunset Tour

Peggys Cove Sunset Tour

£52
per adult
Peggys Cove Sunset Tour
See all activities in Chester

* 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.