Book Holiday Homes in Chesters

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chesters

3 Large Bedroom Ground Floor

3 Large Bedroom Ground Floor

Galashiels
With a stay at this vacation home in Galashiels, you'll be within a 15-minute walk of Bank Street Gardens and Old Gala House.
3 Large Bedroom Ground Floor
The Five Turrets: Stay in Scotland in Style in a Historic Four-bed Holiday Home

The Five Turrets: Stay in Scotland in Style in a Historic Four-bed Holiday Home

4.5 out of 5
Selkirk
When you a stay at this vacation home in Selkirk, you'll be in the mountains, within a 5-minute walk of Market Square and Sir Walter Scott's Courtroom.
The Five Turrets: Stay in Scotland in Style in a Historic Four-bed Holiday Home
Gorgeous Arts & Craft period house with 8 ensuite bedrooms

Gorgeous Arts & Craft period house with 8 ensuite bedrooms

Galashiels
When you stay at this vacation home in Galashiels, you'll be on a river, within a 5-minute drive of Old Gala House and Bank Street Gardens.
Gorgeous Arts & Craft period house with 8 ensuite bedrooms
Save an average of 15% on thousands of hotels when you're signed in
The Old Smithy Converted Blacksmiths - Sleeps 7  and pet friendly (upto 2 dogs)

The Old Smithy Converted Blacksmiths - Sleeps 7 and pet friendly (upto 2 dogs)

Kelso
Located in Kelso, this vacation home is in a rural location, within a 5-minute drive of Kelso Racecourse and Kelso Old Parish Church.
The Old Smithy Converted Blacksmiths - Sleeps 7 and pet friendly (upto 2 dogs)
Host & Stay | Crackin' View

Host & Stay | Crackin' View

Hexham
Located in Hexham, this vacation home is in a rural location, within a 5-minute drive of Bellingham Golf Club and Northumberland National Park.
Host & Stay | Crackin' View
Modern and spacious three bedroom townhouse in Kelso, Scottish Borders

Modern and spacious three bedroom townhouse in Kelso, Scottish Borders

Kelso
With a stay at this vacation home in Kelso, you'll be a 5-minute walk from Kelso Abbey and 5 minutes by foot from Borders Abbeys Way.
Modern and spacious three bedroom townhouse in Kelso, Scottish Borders
Lovely home with garden located centrally in Kelso, Scottish Borders

Lovely home with garden located centrally in Kelso, Scottish Borders

Kelso
When you stay at this vacation home in Kelso, you'll be on a river, within a 10-minute walk of Kelso Old Parish Church and Borders Abbeys Way.
Lovely home with garden located centrally in Kelso, Scottish Borders
World famous house in the beautiful Scottish Borders

World famous house in the beautiful Scottish Borders

Melrose
With a stay at this vacation home in Melrose, you'll be on a river, just steps from Abbotsford The Home Of Sir Walter Scott and a 3-minute drive from Waverley ...
World famous house in the beautiful Scottish Borders
Stylish comfortable self catering cottage . In the heart of the Scottish Borders

Stylish comfortable self catering cottage . In the heart of the Scottish Borders

Jedburgh
Located in Jedburgh, this vacation home is on a river, within a 10-minute drive of Mary Queen of Scots House and Jedburgh Abbey.
Stylish comfortable self catering cottage . In the heart of the Scottish Borders
Don't see what you're looking for?
See all available properties in Chesters
View all properties
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.

Chesters Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chesters vacation homes are the perfect way for you to wing it.

Holiday houses in Chesters let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chesters in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chesters adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesters with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chesters vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chesters Holiday Homes essential information

Accommodation
58 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
3 Large Bedroom Ground Floor, The Five Turrets: Stay in Scotland in Style in a Historic Four-bed Holiday Home, Gorgeous Arts & Craft period house with 8 ensuite bedrooms, The Old Smithy Converted Blacksmiths - Sleeps 7 and pet friendly (upto 2 dogs), Host & Stay | Crackin' View, Modern and spacious three bedroom townhouse in Kelso, Scottish Borders, Lovely home with garden located centrally in Kelso, Scottish Borders, World famous house in the beautiful Scottish Borders, Stylish comfortable self catering cottage . In the heart of the Scottish Borders

Top trending hotels in Chesters

Dryburgh Abbey Hotel

Dryburgh Abbey Hotel

3 out of 5
St Boswells, Melrose, Scotland
Fully refundableReserve now, pay when you stay
Located in Melrose, Dryburgh Abbey Hotel is on a river, a 4-minute walk from Dryburgh Abbey and within a 5-minute drive of Scott's View.
Dryburgh Abbey Hotel
 Le Petit Chateau & William de Percy

Le Petit Chateau & William de Percy

4 out of 5
Jedburgh Road, Otterburn, Northumberland, Newcastle-upon-Tyne, England
Located in Newcastle-upon-Tyne, Le Petit Chateau & William de Percy is in a national park, within a 15-minute drive of Northumberland National Park and Kirkharle ...
Le Petit Chateau & William de Percy
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
Located in Kelso, SCHLOSS Roxburghe, part of Destination by Hyatt is on a river, within a 15-minute drive of Kelso Abbey and Kelso Racecourse.
SCHLOSS Roxburghe, part of Destination by Hyatt
Save an average of 15% on thousands of hotels when you're signed in
George and Abbotsford Hotel

George and Abbotsford Hotel

3.5 out of 5
High Street, Melrose, Scotland
Fully refundableReserve now, pay when you stay
With a stay at George and Abbotsford Hotel in Melrose, you'll be within a 5-minute walk of Saint Cuthbert's Way and Melrose Abbey.
George and Abbotsford Hotel
Don't see what you're looking for?
See all available properties in Chesters
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.