Book Holiday Homes in Chesters

Start date: Check-in selected.
To Date
End date: Check-out

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

MONTEVIOT STABLES WEST - woodland trails and inspirational gardens, 4 bedroom

MONTEVIOT STABLES WEST - woodland trails and inspirational gardens, 4 bedroom

Jedburgh
Located in Jedburgh, this vacation home is in a rural location, within a 15-minute walk of Monteviot House and Woodside Garden Centre.
Opens in a new windowMONTEVIOT STABLES WEST - woodland trails and inspirational gardens, 4 bedroom
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
The Five Turrets Ettrick Terrace, Selkirk, Scotland
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.
Opens in a new windowThe Five Turrets: Stay in Scotland in Style in a Historic Four-bed Holiday Home
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 ...
Opens in a new windowWorld famous house in the beautiful Scottish Borders
Save an average of 15% on thousands of hotels when you're signed in
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.
Opens in a new windowGorgeous Arts & Craft period house with 8 ensuite bedrooms
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.
Opens in a new windowLovely home with garden located centrally in Kelso, Scottish Borders
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.
Opens in a new windowThe Old Smithy Converted Blacksmiths - Sleeps 7 and pet friendly (upto 2 dogs)
Stunning Church Conversion located near to Kelso, Scottish Borders

Stunning Church Conversion located near to Kelso, Scottish Borders

Kelso
Located in Kelso, this vacation home is in a rural location, within a 15-minute walk of Kelso Old Parish Church and Kelso Abbey.
Opens in a new windowStunning Church Conversion located near to Kelso, Scottish Borders
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.
Opens in a new windowModern and spacious three bedroom townhouse in Kelso, Scottish Borders
Hillcrest - 8 Person Luxury House and Hot Tub

Hillcrest - 8 Person Luxury House and Hot Tub

3.5 out of 5
Hawick
With a stay at this vacation home in Hawick, you'll be within a 10-minute drive of The Borders Distillery and Heart of Hawick.
Opens in a new windowHillcrest - 8 Person Luxury House and Hot Tub
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
47 Holiday Homes
Lowest Price
AU$208
Highest Price
AU$504
Popular accommodation
MONTEVIOT STABLES WEST - woodland trails and inspirational gardens, 4 bedroom, The Five Turrets: Stay in Scotland in Style in a Historic Four-bed Holiday Home, World famous house in the beautiful Scottish Borders, Gorgeous Arts & Craft period house with 8 ensuite bedrooms, Lovely home with garden located centrally in Kelso, Scottish Borders, The Old Smithy Converted Blacksmiths - Sleeps 7 and pet friendly (upto 2 dogs), Stunning Church Conversion located near to Kelso, Scottish Borders, Modern and spacious three bedroom townhouse in Kelso, Scottish Borders, Hillcrest - 8 Person Luxury House and Hot Tub

Top trending hotels in Chesters

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
The price is AU$504 per night from 27 Oct to 28 Oct
AU$504
27 Oct - 28 Oct
includes taxes & fees
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.
Opens in a new windowSCHLOSS 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
The price is AU$208 per night from 16 Nov to 17 Nov
AU$208
16 Nov - 17 Nov
includes taxes & fees
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.
Opens in a new windowDryburgh Abbey Hotel
Ednam House Hotel

Ednam House Hotel

3 out of 5
Bridge St, Kelso, Scotland
Fully refundableReserve now, pay when you stay
A stay at Ednam House Hotel places you in the heart of Kelso, steps from Kelso Abbey and Borders Abbeys Way.
Opens in a new windowEdnam House Hotel
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.
Opens in a new windowGeorge 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.