50 Best Cheltenham Apartments on Holiday Lettings - Estates

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125 Vacation rentals

(31) Excellent 

40

Vacation farmhouse in Cheltenham

Cheltenham / Cheltenham

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
*** Awarded Quality in Tourism 4 Star Gold *** Detached Cotswold stone farmhouse situated in an area of outstanding natural beauty. Situated above Woodmancote near Bishops Cleeve, the farmhouse enjoys incredible panoramic views across Cheltenham, Tewkesbury and towards  …see more

from $313 / night

$1999 - $2500 / week

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from $313 / night

20

Vacation cottage with golf nearby in Cleeve Hill

Cheltenham / Cleeve Hill

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Amazing location, ideal for a relaxing break in the Cotswolds. Family house (not a holiday chalet) in the middle of Cleeve Common, with gardens and fantastic views over historic, Regency Cheltenham Spa. Sleeps 7 people easily in 3 double bedrooms and one singl  …see more

from $200 / night

$938 - $2315 / week

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from $200 / night

(4) Excellent 

20

Vacation cottage with golf nearby in Charlton Kings

Cheltenham / Charlton Kings

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
You’ll find King’s Cottage on the edge of Cheltenham in Charlton Kings. You are just minutes away from the Cotswolds and its delightful villages and exquisite countryside. Of course Cheltenham itself has so much to offer too, a vibrant regency town with fabu  …see more

from $125 / night

$688 - $788 / week

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from $125 / night

(14) Excellent 

23

Cheltenham Vacation apartment rental

Cheltenham / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Car not necessary
  • Air conditioning
Apartment 3 is a one bedroom, Five Star, Gold Award apartment in the very heart of Cheltenham. Private parking space provided immediately outside.Ideal for any of the Cheltenham Festivals or for seeing the Cotswolds. Book directly with the owner at official website u  …see more

from $178 / night

$982 / week

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from $178 / night

8

Vacation home in Guiting Power

Cheltenham / Guiting Power

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
The Coach House is a detached property in the grounds of the Grade II listed 16th century Old Rectory. Hawling is an unspoilt village eight miles from Cheltenham, situated at the highest point of the Cotswolds.The nearest shop and pub at Guiting Power is  …see more

from $228 / night

$1590 - $2162 / week

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from $228 / night

(47) Excellent 

23

Vacation home rental

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
Living room with wood-burning stove, French doors to garden and tiled floor/dining room with kitchen area. First floor: Double bedroom with 5ft 6in bed. Further double bedroom with additional single bed (for alternative sleeping only). Bathroom with over-bath shower and  …see more

from $157 / night

$625 - $1500 / week

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from $157 / night

(5) Very Good 

34

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Nearest beach 95 mi
  • Car not necessary
This lovely 2 bedroomed ground floor apartment with private and secure parking for 2 vehicles is situated in the sought after Montpellier area of Cheltenham. It offers two spacious double bedrooms, one with ensuite facilities with a double shower. The second bathroom  …see more

from $119 / night

$688 - $1625 / week

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from $119 / night

(3) Excellent 

18

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
We can accommodate up to a maximum of 5 people plus a baby. Travel cot available. The 4* Courtyard Apartment at Vine Court offers 2 bedrooms (1 double and 1 single plus a double sofa bed in the sitting room) , a large country kitchen/diner with dishwasher, range cook  …see more

from $200 / night

$719 - $938 / week

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from $200 / night

(18) Very Good 

12

Vacation apartment rental

Cheltenham / Cheltenham

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 mi
  • Child friendly
  • Car not necessary
The Garden Apartment has its own entrance and small terrace with garden table and chairs. The accommodation consists of a double bedroom with bathroom en-suite together with a double futon in the living room for two additional people. A £10 extra linen charge is a  …see more

from $82 / night

$569 / week

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from $82 / night

(1) Excellent 

30

Charlton Kings Vacation studio rental

Cheltenham / Charlton Kings

Studio 2 1 night min

  • Studio
  • Sleeps 2
  • 1 night min
  • Ask about pets
This Brand New property was built as a granny flat / nannie's flat in the grounds to our house. We have young family with four children but the Annexe is entirely self contained including its own entrance. We are in walking distance to Cheltenham Town centr  …see more

from $75 / night

$300 / week

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from $75 / night

13

Vacation cottage rental

Cheltenham / Charlton Kings

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
Derrybrook Cottage stands in the grounds of Seven Springs Cottages. It is one of six self-catering cottages offering excellent facilities for couples and friends wishing to enjoy all that the Cotswolds and Cheltenham have to offer. It has a twin bedroom with beds that c  …see more

from $63 / night

$363 - $688 / week

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from $63 / night

(5) Excellent 

19

Vacation apartment in Montpellier suburb

Cheltenham / Montpellier suburb

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
A beautiful Regency two bedroom apartment in the heart of the Montpellier, Cheltenham. Tastefully furnished and decorated, the limestone quarry tiled living room leads onto a peaceful paved garden. If it's chilly then cosy up on the large comfortable sofas with t  …see more

from $232 / night

$1625 / week

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from $232 / night

(3) Excellent 

4

Vacation barn in Cheltenham

Cheltenham / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
The Coach House is situated on the A38 halfway between Gloucester and Tewkesbury, and about 5 miles west of Cheltenham. It provides an ideal base for exploring the Cotswolds, The Forest of Dean, or even the Wye Valley and beyond to the Welsh hills.The barn has  …see more

from $100 / night

$438 / week

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from $100 / night

(5) Very Good 

19

Vacation cottage with golf nearby in Charlton Kings

Cheltenham / Charlton Kings

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Nethercote Cottage stands in the grounds of Seven Springs Cottages. It is one of six self-catering cottages offering excellent facilities for couples wishing to enjoy all that the Cotswolds and Cheltenham have to offer. It has a double bedroom, newly fitted bathroom a  …see more

from $63 / night

$363 - $813 / week

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from $63 / night

12

Cheltenham Vacation apartment rental

Cotswolds / Cheltenham

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
Ideally located in Cheltenham town centre, our 2 bedroom modern top floor (third floor) flat is near to Cheltenham's popular shops, restaurants and bars. Montpellier is a 5 minute walk. Overlooking Leckhampton in the distance, the balcony provides a pleasant space  …see more

from $63 / night

$425 / week

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from $63 / night

(6) Very Good 

16

Vacation cottage in Charlton Kings

Cheltenham / Charlton Kings

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Sherbourne Cottage stands in the grounds of Seven Springs Cottages. It is one of six self-catering cottages offering excellent facilities for families and groups wishing to enjoy all that the Cotswolds and Cheltenham have to offer. It has one double and one twin bedroom  …see more

from $113 / night

$625 - $813 / week

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from $113 / night

(3) Excellent 

24

Vacation home rental

Cotswolds / Cheltenham

5 14 Min stay varies

  • 5 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
This beautiful large modern family home is in the perfect location for the Cheltenham Festival with views over the whole town from its lofty spot near Leckhampton Hill. Surrounded by a large and private hillside woodland with tree covered walks, this stunning contempora  …see more

from $975 / night

$6250 - $9375 / week

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from $975 / night

(3) Good 

14

Cheltenham Vacation apartment rental

Cheltenham / Cheltenham

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
This contemporary second floor apartment with two double bedrooms is situated in a side street just off the main Promenade in the centre of town, and includes a parking space in a gated, secure private car park. It is within easy walking distance of the High Street,  …see more

from $169 / night

$907 - $1063 / week

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from $169 / night

(10) Excellent 

12

Vacation chalet rental

Cheltenham / Charlton Kings

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Wellinghill Lodge is a newly constructed chalet situated down a quiet lane overlooking fields leading to the Cotswold Way, yet just minutes in a car from the centre of Cheltenham. Look out the window and see the hens strutting freely in the field. Enjoy fresh eggs for b  …see more

from $119 / night

$500 / week

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from $119 / night

(3) Very Good 

16

Home rental in Cheltenham

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Car not necessary
Originally built in the 1850's The Coach House was once a two story stone workshop with views overlooking Leckhampton Hill. It was extended, modernised and refurbished in 2011, becoming a 1 bedroomed detached house. With it's own private entrance and patio,  …see more

from $100 / night

$563 / week

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from $100 / night

(3) Excellent 

9

Vacation cottage with golf nearby in Cheltenham

Cheltenham / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Hazleford Cottage stands in the grounds of Seven Springs Cottages. It is one of six self-catering cottages offering excellent facilities for couples wishing to enjoy all that the Cotswolds and Cheltenham have to offer. It has a double bedroom, newly fitted bathroom and  …see more

from $63 / night

$363 - $688 / week

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from $63 / night

(3) Excellent 

10

Montpellier suburb Vacation apartment rental

Cheltenham / Montpellier suburb

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
This beautiful one-bedroom serviced apartment in Cheltenham is located in the fashionable district of Lansdown. Drift upstairs via the fabulous spiral staircase to the spacious bedroom, and enjoy the light and airy living room's balcony which boasts views of the co  …see more

from $173 / night

$1000 / week

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from $173 / night

(1) Excellent 

18

Southam Vacation barn rental

Cheltenham / Southam

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
Furlong Barn is a beautiful property in a stunning, secluded position, enjoying uninterrupted views across Warwickshire farmland from all aspects. This comes with the added advantage of being on the edge of the pretty village of Long Itchington, with its pond and villag  …see more

from $340 / night

$2374 - $4373 / week

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from $340 / night

15

Apartment rental in Prestbury

Cheltenham / Prestbury

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Suitable for children age 5+
  • Private garden
Contemporary Garden Apartment, in the Cotswold village of prestbury: * Modern Kitchen * Spacious Living Area * Luxury Roll Top Bath & Power Shower * 2/3 Bedrooms + Laptop/office area * Walking distance to Pubs & Racecourse * Sleeps 4  …see more

from $107 / night

$619 - $1144 / week

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from $107 / night

(8) Excellent 

21

Home rental in Prestbury

Cheltenham / Prestbury

6 16 Min stay varies

  • 6 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
A stunning contemporary house in a quiet residential area. All year heated (26-30degC - YES heated ALL YEAR - even in the depths of winter!) outdoor constant depth (1.4m) pool with childsafe electric cover (open/close at the touch of a button), full 7 seater hot tub (w  …see more

from $813 / night

$5625 - $8750 / week

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from $813 / night

13

Vacation apartment in Leckhampton

Cheltenham / Leckhampton

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about pets
The famous Cotswold Way is located on the doorstep of this lovely one bedroom self contained annexe flat situated within the grounds of a 19th century town house on Leckhampton Hill and built in local Cotswold Stone. This property is well appointed, having been refurbis  …see more

from $94 / night

$657 / week

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from $94 / night

19

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
This is a spacious airy 1 bedroom apartment located on the 2nd floor. This apartment is fully furnished throughout with an open kitchen and lounge area a bathroom with a shower unit. The apartment is in a great central location in Cheltenham within walking distance to  …see more

from $144 / night

$1007 / week

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from $144 / night

(5) Very Good 

20

Vacation apartment in Prestbury

Cheltenham / Prestbury

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Individual en suite rooms or the whole apartment available. Bonus: easy access to racecourse, town and the Cotswold villages. 130.00 for 1 night, 200.00 for 2 nights. This modern style Penthouse Apartment is located in a beautiful, prime location of Cheltenham.There ar  …see more

from $188 / night

$688 - $1388 / week

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from $188 / night

(5) Very Good 

10

Vacation apartment in Montpellier suburb

Cheltenham / Montpellier suburb

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 94 mi
  • Child friendly
  • Car not necessary
Located in the heart of the popular Montpellier area of Cheltenham, with its' abundance of designer shops, restaurants and pavement cafes, Lansdown Place is a beautiful two bedroom / two bathroom apartment in a great location. The beds can be configured as two King  …see more

from $250 / night

$1225 / week

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from $250 / night

(1) Excellent 

9

Apartment rental in Montpellier suburb with golf nearby

Cheltenham / Montpellier suburb

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Suitable for children age 5+
  • Car not necessary
We are offering a 2 bedroom apartment adjoining our Longworth villa. The apartment includes a lounge/dining area. A contemporary kitchen including electric hob/cooker washing machine. Bathroom with basin, w.c. and P shape bath/shower. Double bedroom with double bed ward  …see more

from $187 / night

$732 - $1082 / week

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from $187 / night

8

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
St James Walk apartment is a spacious 1 bedroom property in the heart of Cheltenham town centre, with easy access to Fitness First and the The Brewery leisure complex, which includes some of Cheltenham's finest bars and restaurants, also just a stones throw away ar  …see more

from $107 / night

$744 / week

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from $107 / night

9

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
This property is located in the heart of Cheltenham Town Centre with all amenities on your doorstep. The 2nd floor houses a Large Kitchen area, Newly fitted with Electric Oven and Hob, Washer dryer, Fridge and Freezer, Large Living/dining room with a feature firep  …see more

from $225 / night

$1575 / week

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from $225 / night

(6) Excellent 

28

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
This delightful farm house is approximately 4 miles above the charming ancient Saxon town of Winchcombe and is situated on a 220 acre sheep grazing farm which comprises a small community of four homes. The house was first built in 1949 and extensively rebuilt by the cur  …see more

from $88 / night

$613 / week

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from $88 / night

22

Cheltenham Vacation home rental

Cotswolds / Cheltenham

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
The farmhouse provides excellent accommodation for 8 guests in 4 kingsize/twin bedrooms with the option of further 2 guests on the sofa bed in the separate snug. An additional 'put-you-up' bed is available as is a cot. Downstairs the open-plan kitchen, dining  …see more

from $250 / night

$1500 - $3850 / week

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from $250 / night

(1) Very Good 

5

Apartment rental in Montpellier suburb

Cheltenham / Montpellier suburb

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
The living room has tall ceilings with pretty cornering, and two large Georgian sash windows flood light into this luxury service apartment. Adding character to this lovely, light room. The comfortable sofa bed and arm chair face an exquisite large marble fireplace.The  …see more

from $188 / night

$1088 - $3150 / week

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from $188 / night

6

Apartment rental in Montpellier suburb

Cheltenham / Montpellier suburb

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Recently new to our portfolio, Luxury Apartments are proud to offer this 1 bedroom apartment situated a few minutes from Montpellier. This third floor apartment has been refurbished throughout, giving it a modern but homely feel. Beautiful views can be seen from sash wi  …see more

from $175 / night

$1050 / week

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from $175 / night

(5) Excellent 

11

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Private garden
An immaculate, split level interesting two bedroom period apartment with a private garden this apartment offers luxury accommodation for the discerning. ,Comfortably furnished to a high standard with a well equipped kitchen and large luxury bathroom,, with a walk in  …see more

from $225 / night

$1375 / week

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from $225 / night

(1) Excellent 

5

Vacation home accommodation

Cheltenham / Leckhampton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
Down a quiet back water, you'll find a recently refurbished Coach House. With a modern sleek white kitchen, boasting wooden underfloor heating throughout into the living room. Going upstairs to a tastefully designed double bedroom, where you can relax leaving your  …see more

from $150 / night

$813 / week

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from $150 / night

8

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
The apartment is situated in the heart of Cheltenham, close to all amenities such as restaurants, bars, shops, cinema and the Everyman theatre to name a few. Newly redecorated throughout and fully equipt with everything required for a comfortable stay, such as towels, l  …see more

from $157 / night

$1094 / week

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from $157 / night

9

Vacation home rental

Cotswolds / Cheltenham

6 16 2 nights min

  • 6 bedrooms
  • Sleeps 16
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Fabulous views from this 7 bedroom listed property in Cheltenham. 7th bedroom is in an annex with private entrance and own ensuite and small kitchen area with a king size bed. 2 miles from town centre and 4 miles from Racecourse. Ideal for racing accommodation, family  …see more

from $1375 / night

$7188 - $15938 / week

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from $1375 / night

1