Chesters Vacations from $1,280
Book a Hotel + Flight or Car together to unlock savings
The Latest Chesters vacation packages
Price found within the past 48 hours. Click for updated prices.
First Pleasance Luxury Apartment
Southside
$1,354
per person
Oct 14 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Edinburgh (EDI)
8/10 Very Good! (6 reviews)
It was fine. There were issues with the internet that I messaged the host about, but didn't get a response or resolution.
Reviewed on Jul 24, 2026
233 Leith Apartment
Leith
$1,581
per person
Oct 13 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Edinburgh (EDI)
8.6/10 Excellent! (20 reviews)
The property was fantastic. Very good value, lovely house, very nicely done. Only issue is that the house has no USB outlets or adapter plugs so you must bring your own.
Reviewed on Aug 25, 2026
What to do in Chesters
Jedburgh, Scottish Borders: Bairnkine Farm Tour with Lucy
$32
per adult
In the Footsteps of Sir Walter Scott One Day Tour
$937
per traveler
Chesters Hotel Deals
Dryburgh Abbey Hotel
St Boswells Melrose Scotland
Fully refundableReserve now, pay when you stay
$122 nightly
$146 total
Sep 27 - Sep 28
Total with taxes and fees
8.8/10 Excellent! (946 reviews)
"Very clean spacious room."
Reviewed on Aug 27, 2026
Schloss Roxburghe Golf Resort, Part of Hyatt
Heiton by Kelso Kelso Scotland
Fully refundableReserve now, pay when you stay
$351 nightly
$421 total
Aug 31 - Sep 1
Total with taxes and fees
9.4/10 Exceptional! (363 reviews)
"The staff were genuinely lovely and welcoming, the room was great, and we really enjoyed the spa facilities. There’s a lot to like about the hotel and it’s clear that the team are trying hard to provide a special experience. That said, for the price of the stay, I felt it was missing just a little ..."
Reviewed on Aug 26, 2026
George and Abbotsford Hotel
High Street Melrose Scotland
$108 nightly
$129 total
Sep 3 - Sep 4
Total with taxes and fees
8/10 Very Good! (485 reviews)
"Perfect place for our 1 night stay and early start the next morning"
Reviewed on Aug 24, 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.
Find the Best Chesters Vacation Packages
Chesters Essential Information
Language | English |
|---|---|
Currency | British pounds sterling |
Top Sights | Hermitage Castle, Hawick Museum & Scott Art Gallery and Heart of Hawick |
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Frequently asked questions
How much does a Chesters vacation package cost?
Offering excellent value package deals from $1,280 on Expedia, you'll be surprised at how little a vacation to Chesters costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Chesters?
November, December and January are the best times to look for cheap Chesters vacation packages. Choosing to travel in less busy periods means you'll typically find reduced prices on flights and hotels.
How many days is enough for Chesters?
With a well-organized travel plan, you can easily visit the top Chesters sights in a handful of days. But if you prefer to explore off the beaten track or go on day trips, consider booking your Chesters vacation for longer.
How to find the best Chesters package deals?
Landing a cheap Chesters package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most pocket-friendly Chesters package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Chesters vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging hotels and flights individually. Better still, you can personalize your Chesters escape to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Chesters?
If you're planning a spur-of-the-moment Chesters adventure, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Chesters vacation packages?
Jet off on your dream getaway to Chesters with help from our Book Now, Pay Later vacations. No need to scrimp and save or hold off until your next payday — we've partnered with online lender Affirm to give you more flexibility and choice. Our vacation packages with payment plans allow you to split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to stay on budget and snap up bargains before they disappear.
Explore a world of travel with Expedia
- Jedburgh Hotels
- B&B in Scottish Borders
- Gay friendly Hotels in Scottish Borders
- Ashkirk Hotels
- Scottish Borders Hotels
- Hotels near Mary Queen of Scots House
- Cottages in Scottish Borders
- 5 Star Hotels in Selkirk
- Casino Hotels in Hawick
- Hawick Hotels
- Selkirk Hotels
- Cabin Rentals in Scottish Borders
- Minto Hotels
- Cabin Rentals in Minto
- Farmstay in Scottish Borders
- Hotels & Resorts for Couples in Scottish Borders
- Borders Textile Towerhouse
- Visit Scottish Borders
- Visit Bonchester Bridge
- Visit Lilliesleaf
- Visit Teviothead
- Visit Denholm
- Scottish Borders Vacations
- Halliwell's House Museum
- Visit Chesters
- Dryburgh Abbey
- Visit Heiton
- Visit Hawick
- Hermitage Castle
- Jedburgh Abbey
- Hawick Museum & Scott Art Gallery
- Visit Selkirk
- Visit St Boswells
- Visit Morebattle
- Visit Ashkirk
- Visit Minto
- Visit Newtown St Boswells
- Mary Queen of Scots House
- Visit Jedburgh
- Smailholm Tower
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.