Cottages in Cheltenham

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Cottages in Cheltenham

Your Cheltenham, Gloucestershire search returned 72 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
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
  • Pet FriendlyYes

    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)

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


for 7 nights From $1265

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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
  • Pet FriendlyNo

    4.9★

    Outstanding

  • 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 From $1011

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A wooden building with potted plants and gravel driveway at Wellinghill Lodge in Cheltenham
27
Cheltenham, Cotswolds, GL52
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyYes

    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)

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


for 7 nights From $511

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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
  • Pet FriendlyNo

    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


for 7 nights From $573

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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
  • Pet FriendlyNo

    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 From $637

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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
  • Pet FriendlyNo

    4.9★

    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


for 7 nights From $839

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A wooden cabin with outdoor seating area at Cotswold Nights Ashton Under Hill
20
Ashton Under Hill, Worcestershire, WR11
  • Sleeps6
  • Bedrooms2
  • Pet FriendlyYes

  • Sykes rating

Cotswold Nights is a wonderful countryside retreat in Ashton under Hill, featuring two bedrooms, open-plan living, and a Lazy Spa hot tub for an indulgent escape. (Ref. 1193972)

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


for 7 nights From $1204

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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
  • Pet FriendlyYes

    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)

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


for 7 nights From $540

Last booked yesterday
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A log cabin with a hot tub and picnic bench at Cotswold Nights Away Evesham
16
Ashton Under Hill, Worcestershire, WR11
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

  • Sykes rating

Cotswold Nights Away is a charming cabin in Ashton Under Hill, featuring a private hot tub, open-plan living, two bathrooms, and flexible three-bedroom accommodation. (Ref. 1193979)

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


for 7 nights From $1901

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An outdoor area with a cabin, hot tub, and wooden furniture at Cotswold Nights Away in Evesham
14
Ashton Under Hill, Worcestershire, WR11
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

  • Sykes rating

Cotswold Nights Away is a stylish cabin in Ashton Under Hill, offering a private hot tub, open-plan living space, two bathrooms, and three versatile bedrooms. (Ref. 1194198)

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


for 7 nights From $1901

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

    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
  • Dishwasher
  • Washing machine


for 7 nights From $700

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An exterior view of a house surrounded by trees and a fence at Wellinghill Cottage at Wellinghill House Charlton Kings
33
Cheltenham, Cotswolds, GL52
  • Sleeps4
  • Bedrooms2
  • Pet FriendlyNo

    5.0★

    Perfect

  • Sykes rating

Wellinghill Cottage is a superb barn conversion in Charlton Kings, Gloucestershire, with alpacas onsite and a woodburning stove. Cheltenham 3.1 miles; Gloucester 13.5 miles; Cirencester 14.3 miles. (Ref. 1183374)

  • Wi-fi
  • Dishwasher
  • Washing machine


for 7 nights From $681

Last booked yesterday
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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
  • Pet FriendlyYes

    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)

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


for 7 nights From $456

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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
  • Pet FriendlyNo

    4.9★

    Outstanding

  • 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


for 7 nights From $4328

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An outdoor area with a hot tub and sun loungers at Cotswold Nights Away 1 in Evesham
12
Evesham, Worcestershire, WR11
  • Sleeps6
  • Bedrooms3
  • Pet FriendlyYes

  • Sykes rating

Cotswold Nights Away 1, a pleasing, pet-friendly holiday lodge located in Evesham, Worcestershire, has a open-plan layout, nearby amenities, and a hot tub. Stratford-upon-Avon 14 miles; Worcester 16 miles; Cheltenham 17 miles. (Ref. 1191051)

  • Pets go free
  • Wi-fi
  • Hot Tub


for 7 nights From $1901

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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
  • Pet FriendlyYes

    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)

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


for 7 nights From $975

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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
  • Pet FriendlyYes

    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)

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


for 7 nights From $1238

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A stone house with large windows and doors surrounded by grass and trees at Hetty's Stables in Aylworth nr Naunton
30
Aylworth nr Naunton, Cotswolds, GL54
  • Sleeps7
  • Bedrooms3
  • Pet FriendlyNo

    4.9★

    Outstanding

  • Sykes rating

Peacefully located in the hamlet of Aylworth, close to Naunton, rests Hetty’s Stables which is a stunning barn conversion in the grounds of Aylworth Cottage. Underfloor heating. Woodburning stove. WiFi. Off-road parking. En-suite bedrooms. Naunton 1.5 mil (Ref. 1091364)

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


for 7 nights From $1227

Last booked yesterday
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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
  • Pet FriendlyYes

    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)

  • Pets go free
  • Wi-fi
  • Dishwasher
  • Washing machine
  • Baby-friendly
  • Sky TV


for 7 nights From $532

Last booked 3 days ago
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An outdoor area with a stone building and gravel pathway at Farm View Annex in Painswick
New property
38
Painswick, Cotswolds, GL6
  • Sleeps2
  • Bedrooms1
  • Pet FriendlyNo

    4.8★

    Outstanding

  • Sykes rating

Farm View Annex is a charming holiday annex in Painswick, Gloucestershire, offering off‑road parking in a peaceful Cotswold setting. Stroud 4.3 miles; Gloucester 7.5 miles; Cheltenham 9.7 miles. (Ref. 1196003)

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


for 7 nights From $615

Last booked yesterday
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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, Evesham, Gloucester, Moreton-in-Marsh, Tewkesbury, 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.