Weekend Breaks Chester

Your Chester, Cheshire search returned 103 cottages

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A property's star rating is the average of the star ratings received from guests that wish for their review to be published

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

The Stable Block is a detached, stable conversion situated in a quiet location on the outskirts of Chester, Cheshire. Pet-friendly. Smart TV. Enclosed patio. Ellesmere Port 6.9 miles; Liverpool 17.8 miles. (Ref. 1142728)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 3 nights From $601

Last booked yesterday
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  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A wonderful detached bungalow on the outskirts of Chester, Cheshire. Ground-floor living. Enclosed rear garden. Close to local amenities. Conservatory. Liverpool 20.6 miles; Manchester 40.6 miles. (Ref. 1118747)

  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 3 nights From $619

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    5.0

    Perfect

  • Sykes rating

This is a delightful semi-detached barn conversion situated close to the city of Chester in Cheshire. Hot tub. Underfloor heating. Pet-free. Chester 5 miles; Ellesmere Port 4.8 miles; Liverpool 17.8 miles. (Ref. 1051835)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher


for 3 nights From $730

  • Sleeps3
  • Bedrooms2
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

A characterful terraced property resting in the city centre of Chester. Short walk to all amenities. Views of the city walls. WiFi. Liverpool 27.5 miles; Llandudno 46.8 miles. (Ref. 1007949)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 3 nights From $460

  • Sleeps10
  • Bedrooms5
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

Mickle Trafford Manor is a stunning, detached manor house, full of traditional features and en-suite bedrooms resting in the gorgeous city of Chester. Liverpool 19.1 miles; Manchester 39 miles. (Ref. 1171265)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Hot Tub
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room


for 3 nights From $2519

  • Sleeps10
  • Bedrooms5
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

33 Lorne Street is a charming, five-storey, pet-friendly house resting in Chester, Cheshire, boasting private driveway parking and an enclosed garden. Liverpool 27.8 miles; Manchester 43.1 miles. (Ref. 1165071)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 3 nights From $1575

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A superb terraced cottage, boasting both contemporary and traditional charm, providing a great base for a family or two couples to explore Chester and beyond. Open-plan living. Two en-suite bedrooms. All-ground-floor. Chester 5 miles. (Ref. 974561)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher


for 3 nights From $679

  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

Rainbows End is a stylish, well-positioned home resting in Christleton, Cheshire. Close to amenities. Enclosed garden. Contemporary. Open-plan living. Chester 3.7 miles. (Ref. 1144696)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 3 nights From $553

Last booked yesterday
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  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

The Warren is a lovely property in Chester, Cheshire, with ground-floor living and is close to several attractions, including the world-famous Chester Zoo. Liverpool 20.1 miles; Manchester 40 miles. (Ref. 1173260)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From $623

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

This elegant terraced cottage rests close to the city of Chester in Cheshire, making a wonderful retreat for a couple seeking a rural escape. Hot tub. Open-plan living. Chester Zoo 4.3 miles; Chester 5.3 miles. (Ref. 974556)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Hot Tub
  • Dishwasher


for 3 nights From $598

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A tasteful apartment situated in an excellent part of Chester in the North West of England. Along the city walls overlooking the River Dee. Liverpool 17 miles; Manchester 36 miles. (Ref. 984751)

  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Sky TV


for 3 nights From $803

  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Studio is a delightful, contemporary lodge settled into eh outskirts of the village of Christleton, Cheshire, with an enclosed garden and open-plan living. Tarvin 3.1 miles; Chester 4.4 miles; Delamere 8.3 miles. (Ref. 1125541)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher


for 3 nights From $434

  • Sleeps6
  • Bedrooms3
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A neatly-presented three-bedroom holiday home resting in Saughall, Cheshire. Pet-free. Off-road parking. Close to amenities. Open-plan. Chester 4.5 miles. (Ref. 1105821)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Dishwasher
  • Washing machine


for 3 nights From $832

Last booked 2 days ago
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  • Sleeps5
  • Bedrooms3
  • Pet FriendlyNo

    4.6

    Outstanding

  • Sykes rating

8 Nicholas Court is an inviting, three-storey holiday home set in a quiet area of Chester city centre, Cheshire. Off-road parking. Close to amenities. Liverpool 20.8 miles; Manchester 40.7 miles. (Ref. 1144559)

  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • 10% off - Fri 24th Jul to 27th Jul 2026


for 3 nights From $635

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.5

    Outstanding

  • Sykes rating

A traditionally-styled, semi-detached dwelling, resting within Chester city centre. Woodburning stove. Pet-friendly. Private courtyard. Amenities within walking distance. Ellesmere Port 6.9 miles; Liverpool 21.7 miles. (Ref. 1017632)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Dishwasher
  • Washing machine


for 3 nights From $690

  • Sleeps3
  • Bedrooms1
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

A superb ground floor cottage in a peaceful location. Good touring base. Bespoke fittings with amazing attention to detail. Views of hills. Chester 4 miles. (Ref. 915519)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom


for 3 nights From $380

Last booked 2 days ago
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  • Sleeps4
  • Bedrooms3
  • Pet FriendlyNo

    4.8

    Outstanding

  • Sykes rating

A stunning, three-storey Georgian property in a superb riverside position. Open fire. River views. WiFi. Beautiful furnishings. Chester city centre 5 mins walk. (Ref. 922999)

  • Wi-fi


for 3 nights From $1014

  • Sleeps4
  • Bedrooms2
  • Pet FriendlyYes

    4.9

    Outstanding

  • Sykes rating

A superb apartment resting within the village of Bretton in Flintshire, North Wales. All-ground-floor. WiFi. Pet-friendly. Chester 4.8 miles. (Ref. 1008377)

  • Pets go free
  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine


for 3 nights From $460

  • Sleeps7
  • Bedrooms4
  • Pet FriendlyYes

    5.0

    Perfect

  • Sykes rating

Jasmine Cottage is a lovely, Grade-II listed property residing in Dodleston, Cheshire. Pet-friendly. Close to amenities. Electric fire. Near an AONB. Chester 5.5 miles. (Ref. 1140004)

  • Pets go free
  • Wi-fi
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly


for 3 nights From $1006

Last booked yesterday
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  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    4.9

    Outstanding

  • Sykes rating

A beautiful, detached bungalow resting on Timadon Farm in Ashton Hayes, Cheshire. Woodburning stove. Near Delamere Forest. Smart TVs. Off-road parking. Chester 9.4 miles. (Ref. 1096157)

  • Wi-fi
  • Off-road parking
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly


for 3 nights From $655

A short break in Chester is the best way to explore one of England’s most picturesque and historic cities. Whether you're strolling along the River Dee, exploring Chester Cathedral, or visiting the famous Chester Zoo, there’s something for everyone.

Weekend breaks in Chester offer the perfect destination for a memorable short getaway.

Why Chester Short Breaks?

A Chester short break is packed with must-see attractions, making it a fantastic destination for a weekend break. Start your visit with a walk along the Chester City Walls, the oldest and most complete in Britain, whilst heading around the wall. Don’t miss the iconic Eastgate Clock, which is one of the most photographed clocks in the UK.

A visit to Chester Cathedral is also a must, with its breathtaking Gothic architecture and beautiful gardens. There are also a number of events that take place at the cathedral throughout the year, from musical performances to literary events, time your Chester short break right and you might be able to see one.

Also during Chester weekend break, don’t forget to visit the Chester market, with the first permanent building being constructed in 1692 and a brand-new building being created in 2022, it is the perfect place to explore and enjoy a wide variety of worldwide cuisine. There are also a number of great bands and artists who play here throughout the weekend too, so it's a perfect place to dine and enjoy some live music.

For a more relaxed experience, take a scenic stroll along the River Dee or you can enjoy a boat cruise or maybe even rent a paddle or motorboat and navigate the waters in your own time. The wonderful Chester Zoo is a must-visit during a weekend break in Chester, with over 20,000 animals, stunning gardens and countless events; it promises a day of fun for the whole family.

Whether you're looking for history, culture or simply a charming city escape, one thing is for sure, a weekend break in Chester is the perfect choice!

Places to Visit during Chester Weekend Breaks

A Chester short break also allows you to visit other locations close by for something different.

Head along the Welsh coastline to towns such as Conwy and Llandudno, offering stunning views over the Irish sea and a wide range of beaches to explore. Both towns also have a great range of food and drink options, making it the perfect place to explore on your Chester short break.

Or head into the mountain ranges of Snowdonia, maybe even try to tackle the impressive summit of Snowdon while you’re here. There are so many fantastic walking trails around with views as far as the eye can see. Head to villages in the heart of the national park, such as Betws-y-Coed and Beddgelert, to really take in the surroundings of this part of the UK.

There is so much to enjoy during a short break in Chester, an unforgettable holiday awaits!

More Destinations to Visit during a weekend break in Chester:

Llangollen

Mold

Nantwich

Shrewsbury

Stoke-on-Trent

Wrexham

Types of Chester Holidays

Head away for a short break today with a Chester weekend break!

For other alternatives in Chester, take a look at cottages in Chester with a hot tub and dog-friendly cottages in Chester.

Why not take a look at a selection of last-minute deals in Cheshire? If you still haven’t found what you’re looking for there are plenty of other cottages in Chester as well as other short breaks in Cheshire to choose from.