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Featured Holiday Homes in Chesters

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
The  Old Fire Station

The Old Fire Station

Scottish Borders
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.
The Old Fire Station
Gorgeous Arts & Craft period house with 8 ensuite bedrooms

Gorgeous Arts & Craft period house with 8 ensuite bedrooms

Galashiels
Located in Galashiels, this vacation home is on a river, within a 15-minute walk of Waverley Line and Old Gala House.
Gorgeous Arts & Craft period house with 8 ensuite bedrooms
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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.
Stunning Church Conversion located near to Kelso, Scottish Borders
Abbey House, charming traditional historic house. Spectacular views of the Abbey

Abbey House, charming traditional historic house. Spectacular views of the Abbey

Jedburgh
With a stay at this vacation home in Jedburgh, you'll be a 4-minute walk from Jedburgh Castle & Jail Museum and 6 minutes by foot from Mary Queen of Scots ...
Abbey House, charming traditional historic house. Spectacular views of the Abbey
Home from Home Converted Blacksmiths - Sleeps 7  and pet friendly (upto 2 dogs)

Home from Home 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.
Home from Home Converted Blacksmiths - Sleeps 7 and pet friendly (upto 2 dogs)
3 Bedroom 2 bathroom  luxurious lodge with hot tub stunning Northumberland

3 Bedroom 2 bathroom luxurious lodge with hot tub stunning Northumberland

Otterburn
Located in Newcastle-upon-Tyne, this vacation home is in a rural location, within a 15-minute drive of Northumberland National Park and Bellingham Golf ...
3 Bedroom 2 bathroom luxurious lodge with hot tub stunning Northumberland
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
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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
39 Holiday Homes
Lowest Price
AU$159
Highest Price
AU$444
Popular accommodation
The Five Turrets: Stay in Scotland in Style in a Historic Four-bed Holiday Home, The Old Fire Station, Gorgeous Arts & Craft period house with 8 ensuite bedrooms, Stunning Church Conversion located near to Kelso, Scottish Borders, Abbey House, charming traditional historic house. Spectacular views of the Abbey, Home from Home Converted Blacksmiths - Sleeps 7 and pet friendly (upto 2 dogs), 3 Bedroom 2 bathroom luxurious lodge with hot tub stunning Northumberland, Lovely home with garden located centrally in Kelso, Scottish Borders, World famous house in the beautiful 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
The price is AU$202 per night from 1 Dec to 2 Dec
AU$202
includes taxes & fees
1 Dec - 2 Dec
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
George and Abbotsford Hotel

George and Abbotsford Hotel

3.5 out of 5
High Street, Melrose, Scotland
Fully refundableReserve now, pay when you stay
The price is AU$159 per night from 23 Nov to 24 Nov
AU$159
includes taxes & fees
23 Nov - 24 Nov
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
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$444 per night from 4 Dec to 5 Dec
AU$444
includes taxes & fees
4 Dec - 5 Dec
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
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Ednam House Hotel

Ednam House Hotel

3 out of 5
Bridge St, Kelso, Scotland
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 26 Nov to 27 Nov
AU$186
includes taxes & fees
26 Nov - 27 Nov
A stay at Ednam House Hotel places you in the heart of Kelso, steps from Kelso Abbey and Borders Abbeys Way.
Ednam House Hotel
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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.

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^Subject to availability and chosen travel dates.