Chesters Vacations from $1,543

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The Latest Chesters vacation packages

Price found within the past 48 hours. Click for updated prices.
Westlands of Pitlochry

Westlands of Pitlochry

4 out of 5
Price was $2,238, price is now $1,543 per person
$1,543
per person
Sep 14 - Sep 18
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Edinburgh (EDI)
9.6/10 Exceptional! (821 reviews)
The staff/owners were so very welcoming and helpful always looking out for our needs. Even a completely unexpected ride in the rain to the train station! 😊 Breakfast was wonderful with plenty of choices! Room was clean, quiet and ever so relaxing! Would love to return.

Reviewed on Jun 21, 2026

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

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

4 out of 5
Price was $2,271, price is now $1,548 per person
$1,548
per person
Jul 26 - Jul 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Edinburgh (EDI)
9.6/10 Exceptional! (237 reviews)
Great location. Pricy but convenient. Very clean and spacious.

Reviewed on Jun 22, 2026

No1. Apartments St Andrews - South Street

No1. Apartments St Andrews - South Street

4 out of 5
Save 100% on your flight
Price was $2,947, price is now $2,030 per person
$2,030
per person
Jul 26 - Jul 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Edinburgh (EDI)
9.8/10 Exceptional! (49 reviews)
My second time staying. This time the sweet had a beautiful expanded and modern kitchen. However, virtually no dishes, pots or pans and no cutlery. Needless to say it was a beautiful kitchen, but not as much use except to keep things in the fridge. Manager should at least add some cutlery.

Reviewed on May 13, 2026

The Inn On The Mile

The Inn On The Mile

4 out of 5
Old Town Edinburgh
Save 100% on your flight
Price was $3,519, price is now $2,534 per person
$2,534
per person
Aug 27 - Sep 2
found 9 hours ago
Roundtrip flight included
Boston (BOS) to Edinburgh (EDI)
9/10 Wonderful! (725 reviews)
Great location directly on the Mile. No elevator so carrying bags up 3 flights was a challenge. Great access to many restaurants and pubs.

Reviewed on Jun 16, 2026

Rusacks St Andrews

Rusacks St Andrews

5 out of 5
Price was $3,277, price is now $2,394 per person
$2,394
per person
Sep 14 - Sep 18
found 5 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Edinburgh (EDI)
9.4/10 Exceptional! (455 reviews)
The staff was incredible.

Reviewed on Apr 28, 2026

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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

What to do in Chesters

Jedburgh, Scottish Borders: Bairnkine Farm Tour with Lucy

Jedburgh, Scottish Borders: Bairnkine Farm Tour with Lucy

$32
per adult
Jedburgh, Scottish Borders: Bairnkine Farm Tour with Lucy
See all activities in Chesters

Chesters Hotel Deals

Dryburgh Abbey Hotel

Dryburgh Abbey Hotel

3 out of 5
St Boswells Melrose Scotland
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $144 total per night from Jul 19 to Jul 20
$144 total
Jul 19 - Jul 20
Total with taxes and fees
8.8/10 Excellent! (894 reviews)
"Friendly staff clean rooms and gorgeous gardens. Nothing to much trouble for them. Very welcoming."

Reviewed on Jun 17, 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
$278 nightly
The price is $333 total per night from Jun 23 to Jun 24
$333 total
Jun 23 - Jun 24
Total with taxes and fees
9.4/10 Exceptional! (346 reviews)
"All staff were extremely helpfull"

Reviewed on Jun 18, 2026

SCHLOSS Roxburghe, part of Destination by Hyatt
George and Abbotsford Hotel

George and Abbotsford Hotel

3.5 out of 5
High Street Melrose Scotland
$107 nightly
The price is $128 total per night from Jul 18 to Jul 19
$128 total
Jul 18 - Jul 19
Total with taxes and fees
8/10 Very Good! (471 reviews)
"Only one thing the curtains would be better if black out curtains were installed to keep out light apart from that the hotel was fantastic 👌"

Reviewed on Jun 21, 2026

George and Abbotsford Hotel
See all 456 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 $1,543 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.