Chesters Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Chesters Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Heeton Concept Aparthotel Edinburgh Queen Street
Edinburgh City Centre
CA $1,428
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Edinburgh (EDI)
9.4/10 Exceptional! (1,308 reviews)
Rooms need a good clean
Mold and insects, desk staffed got it cleaned
Probably overpriced during tourist season
Reviewed on Aug 13, 2026
Ocean Serviced Apartments
Leith
CA $1,669
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Edinburgh (EDI)
9/10 Wonderful! (622 reviews)
While the location of these apartments are far from the city center, they were very spacious and allowed us to stretch out for a couple nights. The views are fantastic along the sea and a cool breeze allowed us to sleep with the windows open throughout the night each day. A bottle of complimentary wine was much appreciated as was a well stocked set of kitchen utensils. The negatives we experienced were sticky floors in the main living area and the combination washer/dryer unit that would not dry. This caused us to have to stay up very late on our last night trying to dry our clothes before we could pack up and leave for the rest of our vacation.
Reviewed on Aug 15, 2026
No1. Apartments Edinburgh - New Town
Edinburgh City Centre
CA $1,510
per person
Oct 19 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Edinburgh (EDI)
9.6/10 Exceptional! (84 reviews)
Lovely apartment. Have now stayed in Edinburgh and St Andrews apartments. Kitchenette light on utensils/cloths but overall a lovely quality property.
Reviewed on Jul 13, 2026
Ready to book your vacation to Chesters?
Chesters Hotel Deals
Dryburgh Abbey Hotel
St Boswells Melrose Scotland
Fully refundableReserve now, pay when you stay
CA $178
CA $213 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (935 reviews)
"We have had a brilliant time , everything was good food room and staff"
Reviewed on Aug 14, 2026
Schloss Roxburghe Golf Resort, Part of Hyatt
Heiton by Kelso Kelso Scotland
Fully refundableReserve now, pay when you stay
CA $575
CA $689 total
Aug 25 - Aug 26
includes taxes & fees
George and Abbotsford Hotel
High Street Melrose Scotland
CA $149
CA $178 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very good! (483 reviews)
"Stayed here for one night before a running event in Selkirk the next day. The staff were really friendly and advised on parking when I arrived. My room was clean and comfortable. I hadn’t booked a table to eat but they squeezed me in at the bar. My burger was delicious. They also had a great selection ..."
Reviewed on Aug 12, 2026
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.
What to do in Chesters
New Lanark & the Kelpies : Private Day Tour from Edinburgh
CA $732
per adult
In the Footsteps of Sir Walter Scott One Day Tour
CA $1,323
per traveller
Frequently asked questions
How much does a Chesters vacation package cost?
You'll find cheap prices from CA $1,428 on Expedia for your Chesters break. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Chesters costs.
What are the cheapest months to go to Chesters?
January, February and November are great times to search for cheap Chesters vacation packages. Choosing to travel in quieter periods means you'll typically find reduced prices on flights and hotels.
How many days is enough for Chesters?
With a well-organized itinerary, you can easily tick off the most popular Chesters sights in a handful of days. But if you'd like to venture off the beaten track or go on day tours, think about booking your Chesters vacation for longer.
How to find the best Chesters package deals?
Start your search for a Chesters package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Chesters package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Chesters adventure off to a flying start.
Is it cheaper to book a Chesters vacation as a package?
You can enjoy significant savings on your Chesters break by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Chesters?
Score incredible discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Chesters vacation.
How to plan a trip to Chesters?
- Choose when to get away: Check your diary and pack your bags. Your favourite season and the available activities will also help you decide when to vacation in Chesters.
- Set a budget: Consider costs such as transportation, flights and meals when calculating how much to put aside for your trip to Chesters. Then, choose a hotel that fits your budget, whether that's a low-cost option or a high-end retreat.
- Work out your trip length: Think about how much time you'd like to spend discovering Chesters. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
- Bundle your airfare and accommodations: After you've nailed down your trip dates and duration, lock in the perfect Chesters vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
