Cottages in Cheltenham

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Cottages in Cheltenham

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Your Cheltenham, Gloucestershire search returned 59 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

7 nights from $849

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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

7 nights from $863

Last booked 2 days ago
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A side entrance to a brick house with a black metal gate with a Beechnt Cottage sign and a garden with green grass and trees in the background at Beechnut Cottage in Tewkesbury
26
Tewkesbury, Gloucestershire, GL20
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A stylish ground-floor cottage resting in Aston on Carrant, Tewkesbury. Open-plan living. Ideal for couples. Tewkesbury 4 miles. Malvern Hills Area of Outstanding Natural Beauty 20.8 miles. (Ref. 952307)

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

7 nights from $495

Last booked 2 days ago
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A wooden building with potted plants and gravel driveway at Wellinghill Lodge in Cheltenham
27
Cheltenham, Cotswolds, GL52
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

A stunning, detached lodge situated in Cheltenham, Cotswolds. WiFi. Pet-friendly. Open-plan living. Tewkesbury 5.9 miles; Cirencester 14.7 miles. (Ref. 1010167)

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

7 nights from $516

Last booked 2 days ago
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A wooden footbridge over a pond leading to a stone building with a tiled roof at Jackdaw's Roost in Cheltenham
25
Cheltenham, Gloucestershire, GL19
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

This quaint adult only country cottage is situated in The Leigh, Gloucestershire. Woodburner. Pet-friendly. Period features. Tewkesbury 9.5 miles; Cirencester 14.7 miles. (Ref. 991352)

  • Off-road parking
  • Ground floor bedroom
  • Washing machine

7 nights from $550

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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

7 nights from $621

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A stone house with a tiled roof and black windows next to a wooden structure with a tiled roof in a garden at The Alms House East in Forthampton near Tewkesbury
34
Forthampton near Tewkesbury, Gloucestershire, GL19
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.9★

    Outstanding

  • Sykes rating

Alms House West is a delightful holiday home located on the outskirts of the village of Forthampton in Gloucestershire with a toasty woodburning stove. Ledbury 12.1 miles; Gloucester 12.3 miles; Cheltenham 12.6 miles; Malvern 12.4 miles. (Ref. 1159773)

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

7 nights from $790

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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

7 nights from $586

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A stone house with a large window extension and a gravel driveway at The Nook in Jack's Green near Painswick
26
Jack's Green near Painswick, Cotswolds, GL6
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A wonderful cottage resting in Jack's Green, Gloucestershire. Woodburning stoves. Freestanding bath. AGA. Countryside views. Stroud 4.7 miles; Gloucester 9.4 miles; Cheltenham 10.1 miles. (Ref. 1103863)

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

7 nights from $934

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Stone exterior of a barn with a green stable door open a wooden shutter and climbing ivy at Five Mile House Barn in Duntisbourne Abbots near Cirencester
31
Duntisbourne Abbots near Cirencester, Cotswolds, GL7
  • Sleeps6
  • Bedrooms3
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A characterful, Grade II listed dwelling, resting on the outskirts of Cirencester. Woodburning stove. Pets welcome. Stroud 12.8 miles; Gloucester 14.9 miles. (Ref. 1014891)

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

7 nights from $808

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A stone house with a garage and gravel driveway with flower pots at Farm View Lodge in Painswick
25
Painswick, Cotswolds, GL6
  • Sleeps4
  • Bedrooms2
  • PetsNo

    4.8★

    Outstanding

  • Sykes rating

A wonderful cottage sitting on a working farm in Painswick, Gloucestershire. Wonderful views. Partial ground-floor living. Amenities within walking distance. Stroud 4.1 miles; Gloucester 7.7 miles; Cheltenham 9.9 miles. (Ref. 1069818)

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

7 nights from $850

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An outdoor area with a round table and four chairs with cushions on grass outside a stone building with windows and a door at The Compton Cottage in Northleach
31
Northleach, Cotswolds, GL54
  • Sleeps4
  • Bedrooms2
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

Outstanding Cottage in the rolling Cotswolds' countryside. A beautifully crafted cottage for 4 people, good pubs nearby and Cheltenham a short drive away. Perfect retreat! (Ref. 1100672)

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

7 nights from $1136

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A stone cottage with a gravel driveway and garden in front at Spring Cottage in Stroud
32
Stroud, Cotswolds, GL6
  • Sleeps2
  • Bedrooms1
  • PetsYes

    5.0★

    Perfect

  • Sykes rating

A beautiful property set just outside the town of Stroud, Gloucestershire. Reverse level accommodation. Tasteful furnishings. Barbecue. Gloucester 14.3 miles; Cirencester 14.4 miles. (Ref. 1132436)

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

7 nights from $798

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A brick exterior of a house with two doors and windows with climbing plants and a white bench outside at River Cottage in Tewkesbury
21
Tewkesbury, Gloucestershire, GL20
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A 14th century, Grade II listed property situated within the town of Tewkesbury. Along the River Avon. Enclosed rear garden. Pub within a 2-minute walk. Cheltenham 9 miles; Gloucester 11 miles. (Ref. 988216)

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

7 nights from $539

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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

7 nights from $886

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A dining table set with plates and cutlery and a bouquet of flowers next to a living area with a leather sofa a wooden chair a TV and large window at The Coach House in Cheltenham
23
Cheltenham, Gloucestershire, GL51
  • Sleeps2
  • Bedrooms1
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

An idyllic first-floor apartment nestled in the heart of Cheltenham, Gloucestershire. Romantic. Central location. Close to local amenities. Close to Cotswolds AONB. Private patio. Tewkesbury 8.2 miles; Cirencester 16 miles; Stratford-upon-Avon 31.8 miles. (Ref. 1121786)

  • Wi-fi
  • Washing machine

7 nights from $573

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A small stone cottage with climbing plants and gravel in front at Hazel Manor Wing in Painswick
43
Painswick, Cotswolds, GL6
  • Sleeps4
  • Bedrooms2
  • PetsYes

    4.7★

    Outstanding

  • Sykes rating

A very smart and spacious country retreat! Set in the grounds of a large Cotswolds' manor - you are in a beautiful location and some good pubs near too. (Ref. 988694)

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

7 nights from $950

Last booked 2 days ago
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A stone farmhouse with a wooden pergola and outdoor seating surrounded by flowers and greenery at Hammonds Farmhouse in Stroud
85
Stroud, Cotswolds, GL6
  • Sleeps16
  • Bedrooms8
  • PetsNo

    5.0★

    Perfect

  • Sykes rating

Hammonds Farmhouse, a stunning home resting in the outskirts of the town of Stroud in Gloucestershire. In AONB. Woodburning stove. Countryside views. Stonehouse 4.9 miles; Gloucester 9.9 miles; Cheltenham 12.5 miles. (Ref. 1134526)

  • Wi-fi
  • Off-road parking
  • Electric vehicle charging
  • Ground floor bedroom
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Games room

7 nights from $4110

Last booked 2 days ago
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A gravel driveway leading to a large brick house surrounded by trees and grass at The Coach House Apartment in Bredon
29
Bredon, Worcestershire, GL20
  • Sleeps2
  • Bedrooms1
  • PetsNo

    4.9★

    Outstanding

  • Sykes rating

A stunning first-floor apartment situated in the rural village of Bredon in Worcestershire. Romantic retreat. Smart TV. Off-road parking. Tewkesbury 3.6 miles; Pershore 7.1 miles; Malvern 17 miles. (Ref. 1061403)

  • Wi-fi
  • Off-road parking
  • Baby-friendly

7 nights from $527

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Exterior of a corrugated metal cabin with red windows and doors on a grassy lawn at Crows Cabin in Gloucester
19
Gloucester, Gloucestershire, GL19
  • Sleeps2
  • Bedrooms1
  • PetsYes

    4.8★

    Outstanding

  • Sykes rating

A delightful cabin retreat resting on the outskirts of the city of Gloucester. Pet-friendly. Off-road parking. Cheltenham 7 miles. (Ref. 1001980)

  • Off-road parking
  • Ground floor bedroom

7 nights from $366

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Map View

This range of Cheltenham accommodation rests within one of the UK's best-preserved spa towns, promising a holiday experience to remember.

Why Cottages in Cheltenham?

This town, on the western fringes of the Cotswolds AONB, boasts elegant streets lined with Regency architecture, with one of the finest examples being the Pitville Pump Room. Other popular attractions include Cheltenham's Museum and Art Gallery know, The Holst Birthplace Musuem as well as the stylish Montpellier district of the town, a region full of beautiful buildings, boutique shops and restaurants. To discover the best things to do near your Cheltenham cottage, browse through our Cheltenham Travel Guide.

Places to visit near Cheltenham

Cottages in Cheltenham rest at the western gateway to the Cotswolds, making them ideally placed to explore this beautiful Area of Outstanding Natural Beauty. Avid ramblers will be in their element throughout the beauty of the Cotswolds, with many paths and trails coming surrounded by luscious greenery. You will also stumble across a choice of historic and characterful market towns, as well as an assortment of quaint little villages. During your Cheltenham cottage holiday, you may consider visiting popular spots such as Bourton-on-the-Water, Chipping Campden, Gloucester, Moreton-in-Marsh, Stow-on-the-Wold and Stroud.

Types of Cotswolds Holidays

If you're looking to explore the beauty of the Cotswolds on your next trip, find different holiday types to find a perfect break for you. Book a Cotswolds family holiday if you're looking to celebrate that special occasion, or treat yourselves to that extra touch with a choice of luxury Cotswolds cottages. For a unique holiday experience, try a glamping pod in Gloucestershire or Glamping pod in the Cotswolds. You can also choose from these dog-friendly cottages in the Cotswolds.

The wide variety of properties and experience of Sykes will ensure that your adventure is one to remember.