Chesters Vacations from $1,329

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The Latest Chesters vacation packages

Price found within the past 48 hours. Click for updated prices.
Parliament House Hotel

Parliament House Hotel

3 out of 5
Edinburgh City Centre
Price was $1,859, price is now $1,329 per person
$1,329
per person
May 13 - May 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Edinburgh (EDI)
9/10 Wonderful! (1,004 reviews)
Arrived early afternoon, gentleman at reception amazingly helpful as we were unsure as to length of stay due to flight disruptions. Our twin room was well appointed with very comfortable beds and everything we needed. Nice to have somewhere to sit other than the beds as well. Hotel is centrally located and quiet at night. Spotlessly clean and very reasonably priced given its location. We would definitely stay here again

Reviewed on Mar 19, 2026

No1. Apartments St Andrews - South Street

No1. Apartments St Andrews - South Street

4 out of 5
Save 100% on your flight
Price was $3,110, price is now $2,032 per person
$2,032
per person
May 3 - May 7
found 8 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Edinburgh (EDI)
9.8/10 Exceptional! (48 reviews)
Lovely place to stay over Christmas. Can’t believe that cleaners came to tidy in Christmas Day. Beautiful apartment. Bedrooms amazing

Reviewed on Jan 1, 2026

No1. Apartments & Bedrooms St Andrews - St Mary’s

No1. Apartments & Bedrooms St Andrews - St Mary’s

4 out of 5
Price was $2,366, price is now $1,624 per person
$1,624
per person
May 3 - May 7
found 8 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Edinburgh (EDI)
9.6/10 Exceptional! (231 reviews)
The whole house is very clean. Looks like it's newly renovated. It will be great if they can provide tissue paper in the living area It's strategically location, close to everything.. I would definitely stay here if l should visit St Andrews again

Reviewed on Feb 27, 2026

St Stephen Street Apartment

St Stephen Street Apartment

4 out of 5
Edinburgh City Centre
Price was $3,114, price is now $2,282 per person
$2,282
per person
Jun 11 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Edinburgh (EDI)
9/10 Wonderful! (2 reviews)
Historic 6-Bedrooms Castle Retreat

Historic 6-Bedrooms Castle Retreat

2 out of 5
Save 100% on your flight
Price was $8,200, price is now $6,164 per person
$6,164
per person
May 3 - May 7
found 8 hours ago
Roundtrip non-stop flight included
Chicago (ORD) to Edinburgh (EDI)
No reviews
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Discover the most popular places to visit in Chesters

Heart of Hawick

4.5/5(3 reviews)

Enjoy an outing to Heart of Hawick during your stay in 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

Chesters Hotel Deals

Dryburgh Abbey Hotel

Dryburgh Abbey Hotel

3 out of 5
St Boswells Melrose Scotland
Fully refundableReserve now, pay when you stay
$124 nightly
The price is $149 total per night from Mar 29 to Mar 30
$149 total
Mar 29 - Mar 30
Total with taxes and fees
8.6/10 Excellent! (859 reviews)
Comfy and welcoming.

Reviewed on Mar 13, 2026

Dryburgh Abbey Hotel
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
$270 nightly
The price is $324 total per night from Mar 30 to Mar 31
$324 total
Mar 30 - Mar 31
Total with taxes and fees
9.4/10 Exceptional! (301 reviews)
Wonderful Spa - but no availability for treatments for guests

Reviewed on Mar 16, 2026

SCHLOSS Roxburghe, part of Destination by Hyatt
Ednam House Hotel

Ednam House Hotel

3 out of 5
Bridge St Kelso Scotland
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $125 total per night from Apr 6 to Apr 7
$125 total
Apr 6 - Apr 7
Total with taxes and fees
8.4/10 Very Good! (506 reviews)
Lovely

Reviewed on Mar 9, 2026

Ednam House Hotel
See all 452 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 $1,329 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.