Holiday Cottages Winchcombe

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British Travel Award Winners!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards.

Holiday Cottages Winchcombe

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Your Winchcombe, Gloucestershire search returned 23 cottages

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Map View
A street with shops and buildings made of stone and brick at Postmaster's Lodging in Winchcombe
33
Winchcombe, Cotswolds, GL54
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

Postmasters Lodging is set over three floors in Winchcombe, Cotswolds. Open-plan living area. Cheltenham 8 miles; Broadway 9 miles. (Ref. 976759)

  • Wi-fi
  • Dishwasher
  • Baby-friendly


for 7 nights £642

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A row of houses with stone and brick walls blue doors and windows and small planters on the sidewalk at Lower Pack Horse Cottage in Winchcombe
42
Winchcombe, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Lower Pack Horse Cottage is a harmonious Grade-II listed cottage in the town of Winchcombe in Gloucestershire, boasting a woodburning stove and a Smart TV. Cheltenham 7.7 miles; Broadway 10 miles; Gloucester 16.8 miles. (Ref. 1131021)

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


for 7 nights £662

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An exterior view of a house with a wooden door covered by a wooden canopy a stone pathway green grass a small tree and a wooden shed at Old Sorting Office in Winchcombe
13
Winchcombe, Cotswolds, GL54
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

This historic ground floor apartment is located in Winchcombe, Gloucestershire. Romantic. Spacious rooms. Open-plan living. Cheltenham 8 miles; Broadway 9 miles. (Ref. 977985)

  • Wi-fi
  • Ground floor bedroom
  • Baby-friendly


for 7 nights £441

Last booked 2 days ago
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A stone house exterior with potted plants on a paved patio and metal chairs with a table at The Old Cider House in Prestbury near Cheltenham
18
Prestbury near Cheltenham, Cotswolds, GL52
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Beautiful Cotswold stone character property set on 150-acre equestrian centre. En-suite shower room. WiFi. Country walks and equestrian activities on site. 10 minutes to Cheltenham, 7 minutes to Cheltenham racecourse. (Ref. 948400)

  • Wi-fi
  • Off-road parking


for 7 nights £462

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A street view of a row of old stone houses with chimneys and flower boxes at Fern Cottage in Winchcombe
26
Winchcombe, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

This is a mid-terrace cottage situated in the town of Winchcombe, Gloucestershire in the Cotswolds. Enclosed patio and garden. One well-behaved dog welcome. Traditional features. Cheltenham 8.5 miles; Bourton-on-the-Water 11miles. Gloucester 15.6 miles. (Ref. 1012253)

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


for 7 nights £675

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A stone house with a sloped roof next to a lawn and gravel driveway at Tumbledown in Buckland
37
Buckland, Cotswolds, WR12
  • Sleeps6
  • Bedrooms3
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

An outstanding cottage! Beautiful village location, bar across the lane, Broadway 2 miles away. An exceptional cottage choice. (Ref. 988672)

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


for 7 nights £958

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The Garden Retreat - 1159770 - photo 1
32
Winchcombe, Cotswolds, GL54
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

8 Gloucester Street is a charming house in Winchcombe, Gloucestershire, situated in the Cotswolds, boasting a woodburning stove and an enclosed garden. Cheltenham 7.8 miles; Broadway 8.4 miles; Gloucester 14.7 miles. (Ref. 1159770)

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


for 7 nights £478

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Stone cottages with doors and windows on a street at Thimble Cottage in Winchcombe
35
Winchcombe, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A charming terraced cottage situated in the centre of Winchcombe. Pet-friendly. Woodburning stove. Private garden. WiFi. Cheltenham 8.2 miles; Gloucester 15.3 miles. (Ref. 1050024)

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


for 7 nights £609

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A garden with a dining table and chairs on gravel outside a brick house at The Old School House in Dumbleton
34
Dumbleton, Cotswolds, WR11
  • Sleeps8
  • Bedrooms4
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A stunning, four-bedroom home resting in Dumbleton near Alderton, Gloucestershire. Character features. In AONB. Pretty gardens. Open fire. Large. Broadway 6.3 miles; Evesham 7.3 miles; Tewkesbury 8.6 miles. (Ref. 1127215)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Washing machine
  • Baby-friendly


for 7 nights £1309

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The Old Cider Press - 996452 - photo 1
35
Broadway, Cotswolds, WR12
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.4★

    Good

  • Sykes rating

Beautiful thatched cottage which has recently had the bathroom and kitchen refurbished in January 2025. is within a row of three, nestled in the pretty Cotswolds village of Stanton. (Ref. 996452)

  • Wi-fi
  • Ground floor bedroom
  • Washing machine
  • Baby-friendly


for 7 nights £669

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A row of white houses with blue and black doors and shuttered windows at Primrose Cottage in Winchcombe
37
Winchcombe, Cotswolds, GL54
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.5★

    Outstanding

  • Sykes rating

A centrally positioned three-storey cottage resting in Winchcombe, Gloucestershire. Pet-friendly. Within Cotswolds AONB. Private patio. Character features. Cheltenham 8.1 miles; Broadway 8.3 miles; Gloucester 15.1 miles. (Ref. 1092551)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights £591

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A single-story house with a tiled roof next to a driveway and palm trees at Hillside in Bishops Cleeve
28
Bishops Cleeve, Gloucestershire, GL52
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

Hillside is a homely, detached bungalow situated in a quiet residential area of Bishops Cleeve, Gloucestershire, featuring convenient ground-floor living. Cheltenham 5.9 miles; Tewkesbury 9 miles. (Ref. 1175869)

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


for 7 nights £459

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A circular living space with a sofa table kitchenette and bed at Island Yurt in Beckford near Tewkesbury
22
Beckford near Tewkesbury, Worcestershire, GL20
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.3★

    Good

  • Sykes rating

Unusual romantic Gloucestershire yurt by fishing lake. Hot tub, sauna, film projector, veranda. Ideal base for a couple to relax together. Beckford 0.5 miles. (Ref. 903586)

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


for 7 nights £621

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A round yurt structure with windows near a hot tub and outdoor chairs by a lake at Lakeview Yurt in Beckford near Tewkesbury
22
Beckford near Tewkesbury, Cotswolds, GL20
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.6★

    Outstanding

  • Sykes rating

A 20 foot yurt in Gloucestershire. Underfloor heating, roll top bath. Veranda with private hot tub and sauna overlooking the lake just a short stroll from Beckford village. (Ref. 11980)

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


for 7 nights £497

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A yurt with green fabric walls and a door open to a bedroom with a bed surrounded by trees at The Lakeside Yurt in Beckford
19
Beckford, Worcestershire, GL20
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.2★

    Good

  • Sykes rating

A unique Gloucestershire holiday home! A 16 foot round modern yurt, on the edge of the village of Beckford. Roll-top bath. Use of hot tub. Cheltenham 9 miles. (Ref. 6017)

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


for 7 nights £422

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A stone house with a lawn front garden and a gravel driveway at Suncroft in Southam near Prestbury
39
Southam near Prestbury, Cotswolds, GL52
  • Sleeps7
  • Bedrooms4
  • PetsYes

    3.7★

    Good

  • Sykes rating

Suncroft is a characterful, four-bedroom holiday home residing in Southam near Prestbury, Gloucestershire. In an AONB. Woodburning stove. Close to amenities. Cheltenham 3.7 miles; Tewksbury 8.8 miles; Gloucester 10.8 miles; Cirencester 18.2 miles. (Ref. 1132891)

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


for 7 nights £1072

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A building exterior with windows and grass at Flat 2 Battledown Grange in Cheltenham
27
Cheltenham, Gloucestershire, GL52
  • Sleeps4
  • Bedrooms2
  • PetsNo

  • Sykes rating

Flat 2 Battledown Grange is a lovely, ground-floor holiday apartment resting in the charming town of Cheltenham in Gloucestershire near a shop and pub. Tewkesbury 9.7 miles; Cirencester 15.2 miles; Stratford-upon-Avon 30.4 miles. (Ref. 1175215)

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


for 7 nights £492

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A studio with a bed sofa and dining table at Swallow Studio in Andoversford near Cheltenham
19
Andoversford near Cheltenham, Cotswolds, GL54
  • Sleeps2
  • Bedrooms1
  • PetsYes

  • Sykes rating

Swallow Studio is a single-storey, Grade II listed shared unit resting on a working farm in Andoversford, Gloucestershire, with countryside views and open-plan living. Cheltneham 6.6 miles; Bourton-on-the-Water 9.7 miles; Gloucester 13.9 miles. (Ref. 1189950)

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

  • 20% off - Fri 19th Dec 2025 to 5th Jan 2026


for 7 nights £483

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An outdoor area with a hot tub chairs a wood burning stove near a round tent structure by a river at Secret Island Yurt Beckford near Tewkesbury
15
Beckford near Tewkesbury, Worcestershire, GL20
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.4★

    Good

  • Sykes rating

Charming yurt in quaint Gloucestershire village of Beckford. Open plan accommodation. Roll-top bath. Sauna. Private hot tub overlooking the lake. Cheltenham 9 miles. (Ref. 921614)

  • Off-road parking
  • Hot Tub
  • Dishwasher


for 7 nights £654

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A bedroom with a bed, dining table, and sofa at Woodcock Studio in Andoversford near Cheltenham
15
Andoversford near Cheltenham, Cotswolds, GL54
  • Sleeps2
  • Bedrooms1
  • PetsYes

  • Sykes rating

Woodcock Studio is a single-storey, Grade II unit situated on a working farm in Andoversford, Gloucestershire, boasting open-plan living and Smart TV. Cheltenham 6.6 miles; Bourton-on-the-Water 9.7 miles; Gloucester 13.9 miles. (Ref. 1189949)

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

  • 20% off - Fri 19th Dec 2025 to 5th Jan 2026


for 7 nights £483

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Map View

Enjoy easy access to the delights of Gloucestershire, including the beautiful Cotswolds AONB from this collection of Winchcombe cottages.

Why Winchcombe?

The pretty town of Winchcombe rests within the district of Tewkesbury, and on the fringes of the Cotswolds AONB - making it a superb base for holidaymakers of all kinds. Its streets are laced with delightful stone cottages, as well as an assortment of charming cafés, restaurants and shops to enjoy from your Winchcombe accommodation, as well as the fascinating, 15th century Sudeley Castle, wrapped in exquisite gardens. Our Cotswolds Travel Guide is ideal for getting all your ideas and inspiration for a break to remember.

Places to visit near Winchcombe

Explore the stunning northern Cotswolds and beyond from your self-catering Winchcombe cottage. The area is rife with stunning trails for walkers and cyclists to make use of, passing idyllic natural beauty. The rolling fields and far-reaching landscapes are peppered with fascinating towns and villages exuding traditional charm and attractions appealing to all. In the area surrounding Winchcombe cottages you will find attractions such as Broadway Tower, Snowshill Manor and Garden, The Model Village, the Cotswolds Farm Park and more. The most popular places to visit by these Winchcombe self-catering cottages include Bourton-on-the-Water, Cheltenham, Chipping Campden, Evesham, Moreton-in-Marsh, Tewkesbury and Stow-on-the-Wold.

Types of Holidays

Discover a choice of Cotswolds holiday types certain to offer you a perfect place to stay. Don't leave a man or dog behind with pet-friendly Cotswolds cottages, while these family holidays in the Cotswolds are ideal for bringing everyone together for a special occasion. Push the boat out by staying at a luxury Cotswolds cottage or choose a cottage with a hot tub in the Cotswolds for that added special touch.