Chesters Vacations from $1,016

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The Latest Chesters vacation packages

Price found within the past 48 hours. Click for updated prices.
No1. Apartments St Andrews - South Street

No1. Apartments St Andrews - South Street

4 out of 5
Price was $1,476, price is now $1,016 per person
$1,016
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Edinburgh (EDI)
9.8/10 Exceptional! (39 reviews)
The apt was well situated for comfort and easy access to all of St Andrew’s. With 2 locations in town they have a lot of options for single and group travel. I really liked the premium feel to the apartments and was well taken care of in communication with their staff when I had questions during and the option to leave my. Ava before my trip home was very welcome. Thank you!

Reviewed on Apr 26, 2025

JOIVY Observatory House

JOIVY Observatory House

4 out of 5
Old Town Edinburgh
Save 100% on your flight
Price was $3,164, price is now $2,285 per person
$2,285
per person
Dec 3 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Edinburgh (EDI)
No reviews
JOIVY Iconic Cockburn Street 4 Bedroom Apartment: Heart of Old Town

JOIVY Iconic Cockburn Street 4 Bedroom Apartment: Heart of Old Town

3 out of 5
Old Town Edinburgh
Save 100% on your flight
Price was $2,965, price is now $2,174 per person
$2,174
per person
Dec 3 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Edinburgh (EDI)
No reviews
Stewart by Heeton Concept

Stewart by Heeton Concept

4 out of 5
Edinburgh City Centre
Price was $1,456, price is now $1,111 per person
$1,111
per person
Dec 4 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Edinburgh (EDI)
9/10 Wonderful! (841 reviews)
The room was nice and clean. But, the bathroom was poorly ventilated, so it had a stuffy/musty smell. Otherwise, a very enjoyable stay and a nice affordable property!

Reviewed on Oct 23, 2025

The Scotsman Hotel

The Scotsman Hotel

4 out of 5
Old Town Edinburgh
Price was $2,414, price is now $1,845 per person
$1,845
per person
Nov 27 - Dec 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Edinburgh (EDI)
9.2/10 Wonderful! (1,013 reviews)
Great hotel. Pricy but the rooms were spacious and very nice. Lots of construction going on in the area but in an old town that obviously happens. We did not hear anything construction noise from our room.

Reviewed on Oct 21, 2025

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Discover the most popular places to visit in Chesters

Heart of Hawick

4.5/5(3 reviews)

You can learn about the history of Hawick when you stop by Heart of Hawick. While in this relaxing area, you can savor the top-notch restaurants.

Heart of Hawick

Hermitage Castle

Hermitage Castle is just one of the places to see in Hawick, so why not enjoy the other things to explore during your travels? Discover the area's countryside and restaurants.

Hermitage Castle

Borders Textile Towerhouse

You can spend an afternoon exploring the galleries in Borders Textile Towerhouse during your trip to Hawick. While in this relaxing area, you can savor the top-notch restaurants.

Borders Textile Towerhouse

What to do in Chesters

Abbotsford: House, Chapel and Garden Ticket

Abbotsford: House, Chapel and Garden Ticket

$21
per adult
Abbotsford: House, Chapel and Garden Ticket
Lucy speaking to guests about paddock grazing

Bairnkine Farm Tour with the Farmer

$35
per adult
Bairnkine Farm Tour with the Farmer
See all activities in Chesters

Chesters Hotel Deals

SCHLOSS Roxburghe, part of Destination by Hyatt

SCHLOSS Roxburghe, part of Destination by Hyatt

5 out of 5
Heiton, Kelso, Scotland
Fully refundableReserve now, pay when you stay
$271 nightly
The price is $325 total per night from Nov 3 to Nov 4
$325 total
Nov 3 - Nov 4
Total with taxes and fees
9.4/10 Exceptional! (232 reviews)
We had such a lovely weekend here as a family! From the moment we arrived, the staff were so friendly and welcoming. The spa was beautiful and so relaxing, and the treatments were amazing. Our room was spacious, super comfortable. The food was delicious — fresh, full of flavour, and delicious. If ...

Reviewed on Oct 19, 2025

SCHLOSS Roxburghe, part of Destination by Hyatt
Dryburgh Abbey Hotel

Dryburgh Abbey Hotel

3 out of 5
St Boswells, Melrose, Scotland
Fully refundableReserve now, pay when you stay
$117 nightly
The price is $141 total per night from Nov 9 to Nov 10
$141 total
Nov 9 - Nov 10
Total with taxes and fees
8.6/10 Excellent! (832 reviews)
Beautiful property excellent location stunning food and friendly staff

Reviewed on Oct 5, 2025

Dryburgh Abbey Hotel
Ednam House Hotel

Ednam House Hotel

3 out of 5
Bridge St, Kelso, Scotland
$143 nightly
The price is $172 total per night from Oct 28 to Oct 29
$172 total
Oct 28 - Oct 29
Total with taxes and fees
8.4/10 Very Good! (475 reviews)
All good

Reviewed on Oct 10, 2025

Ednam House Hotel
See all 453 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.

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 $1,016 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

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.