Chesters Vacation Packages

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Top Chesters Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Ben Doran Guest House

The Ben Doran Guest House

4 out of 5
Newington
Price was CA $2,033, price is now CA $1,638 per person
CA $1,638
per person
Feb 1 - Feb 7
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Edinburgh (EDI)
8.2/10 Very good! (477 reviews)
I would definitely return.

Reviewed on Nov 11, 2026

Hapimag Resort Edinburgh

Hapimag Resort Edinburgh

4 out of 5
West End
Price was CA $3,114, price is now CA $2,308 per person
CA $2,308
per person
Feb 2 - Feb 8
found 16 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Edinburgh (EDI)
9.8/10 Exceptional! (406 reviews)
This is a great place to stay if you’re looking for a quiet neighborhood without the mobs of tourists. The building is beautiful and quite sprawling. I was on the 2nd floor and had incredible views of Dean village. On clear days you can see quite far beyond the city into the mountains and sea. My room was spacious and well stocked with coffee, espresso, tea, dishes, flatware, etc. I had control over the heat which i loved. The bed was quite comfortable and the furniture was quite nice. The bathroom was incredible… Large tub (I’m 6’) and large shower with a towel heater and radiator for optional heat. The staff was as professional as i expected. Very accommodating and helpful. If you have an issue, i have no doubt they will work diligently to solve it. House keeping was top notch. There’s a honesty shop in the lobby thank god. They have it fully stocked with whites and reds, cokes, seltzer, etc. Snacks abound. The lounges are very comfortable. Overall this was an amazing experience. I will 100% stay here again when in Edinburgh. Thank you for a wonderful experience! Hapimag was the highlight of my trip.

Reviewed on Oct 23, 2026

The Scotsman Hotel

The Scotsman Hotel

4 out of 5
Edinburgh City Centre
Price was CA $7,443, price is now CA $5,566 per person
CA $5,566
per person
Dec 27 - Jan 2
just found
Roundtrip flight included
Montreal (YUL) to Edinburgh (EDI)
9.2/10 Wonderful! (1,004 reviews)

South Lane Apartments - City Centre

South Lane Apartments - City Centre

4 out of 5
Edinburgh City Centre
Price was CA $4,385, price is now CA $3,520 per person
CA $3,520
per person
Dec 26 - Jan 1
found 14 hours ago
Roundtrip flight included
Halifax (YHZ) to Edinburgh (EDI)
8.8/10 Excellent! (8 reviews)

Stewart by Heeton Concept

Stewart by Heeton Concept

4 out of 5
Edinburgh City Centre
Price was CA $6,198, price is now CA $5,027 per person
CA $5,027
per person
Dec 27 - Jan 2
just found
Roundtrip flight included
Montreal (YUL) to Edinburgh (EDI)
9/10 Wonderful! (960 reviews)

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Chesters Hotel Deals

Dryburgh Abbey Hotel

Dryburgh Abbey Hotel

3 out of 5
St Boswells Melrose Scotland
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Nov 18 to Nov 19
CA $169
CA $203 total
Nov 18 - Nov 19
includes taxes & fees
8.8/10 Excellent! (995 reviews)
"Always love staying here, staff super friendly. Easy parking and perfect grounds and super dog friendly for our crazy boxer dog Kai."

Reviewed on Nov 14, 2026

Dryburgh Abbey Hotel
Schloss Roxburghe Golf Resort, Part of Destination by Hyatt

Schloss Roxburghe Golf Resort, Part of Destination by Hyatt

5 out of 5
Heiton by Kelso Kelso Scotland
Fully refundableReserve now, pay when you stay
The price is CA $368 per night from Nov 18 to Nov 19
CA $368
CA $442 total
Nov 18 - Nov 19
includes taxes & fees
9.4/10 Exceptional! (395 reviews)
"Amazing 2 night stay at the Schloss hotel. The staff were brilliant and consistently went above and beyond. Both restaurants- Charlie’s and Sunlaws were both so good! Spa was great too although the hot tub and pool weren’t quite as hot as expected. Overall really impressed and will definitely be ..."

Reviewed on Nov 14, 2026

Schloss Roxburghe Golf Resort, Part of Destination by Hyatt
George and Abbotsford Hotel

George and Abbotsford Hotel

3.5 out of 5
High Street Melrose Scotland
The price is CA $149 per night from Dec 16 to Dec 17
CA $149
CA $179 total
Dec 16 - Dec 17
includes taxes & fees
8/10 Very good! (509 reviews)
"Okay but a little tired in terms of condition"

Reviewed on Nov 14, 2026

George and Abbotsford Hotel
See all 538 properties in Chesters
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.
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What to do in Chesters

In the Footsteps of Sir Walter Scott One Day Tour

In the Footsteps of Sir Walter Scott One Day Tour

CA $1,323
per traveller
In the Footsteps of Sir Walter Scott One Day Tour
The Kelpies

New Lanark & the Kelpies : Private Day Tour from Edinburgh

CA $2,740
per adult
New Lanark & the Kelpies : Private Day Tour from Edinburgh
See all activities in Chesters

Frequently asked questions

How much does a Chesters vacation package cost?
You'll find cheap prices from CA $1,638 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.