50 Best Cheltenham Apartments on Holiday Lettings - Estates

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Charlton Kings
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1,314 Vacation rentals

(17) Excellent 

25

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 single. (A …see more

from $211 / night

$1,052 - $2,041 / week

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avg. 1 hour 30 minutes

from $211 / night

(48) 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 $383 / night

$2,105 - $3,635 / week

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from $383 / night

(6) 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 $77 / night

$383 - $702 / week

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from $77 / night

(3) Very Good 

19

Cottage rental in Cheltenham

Cotswolds / Cheltenham

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
Windrush 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 a double bedroom and two twin bed …see more

from $147 / night

$957 - $1,059 / week

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from $147 / night

(11) Very Good 

19

Vacation cottage with golf nearby in Cheltenham

Cotswolds / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • 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 $83 / night

$415 / week

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Responds fast!
avg. 3 hours 44 minutes

from $83 / night

(1) Excellent 

45

Vacation home in Cheltenham

Cotswolds / Cheltenham

7 20 min stay varies

  • 7 bedrooms
  • sleeps 20
  • min stay varies
  • Child friendly
  • Private garden
8 bedrooms 5 bathrooms, 3 of which are ensuite 2 cloakrooms Beautiful orangery dining room seating 12 Stunning panaramic views & garden Fully equipped gourmet kitchen 3 Reception rooms Boot & Utility Room All Principle rooms access terrace / garden As the electric gat …see more

from $1,658 / night

$5,102 - $15,049 / week

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from $1,658 / night

(1) Excellent 

13

Vacation cottage rental

Cotswolds / Cheltenham

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • 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 $83 / night

$447 - $485 / week

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from $83 / night

12

Cheltenham Vacation home rental

Cotswolds / Cheltenham

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
Modern 2 double bedroom townhouse with parking in central Cheltenham. Conveniently located just a short stroll from Cheltenham town centre with easy access to shops, cafes and restaurants and only 2 miles from Cheltenham Racecourse. Cedar Court townhouse is located in …see more

from $128 / night

$894 - $1,073 / week

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from $128 / night

(5) Excellent 

19

Vacation barn in Cheltenham

Cotswolds / Cheltenham

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Park Bothy is so gorgeous! A cute Cotswolds' bolt hole, furnished to a very high standard AND with its own, private Hot Tub. The barn has been beautifully renovated to create a truly attractive holiday retreat. You have a private entrance, set off and away from the lane …see more

from $156 / night

$619 - $782 / week

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from $156 / night

(3) Very Good 

29

Vacation cottage rental

Cheltenham / Charlton Kings

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly
The elegant Regency Spa Town of Cheltenham is located on the western boundaries of the Cotswolds seven miles east of Gloucester and within easy reach of the M5. It is a bustling popular shopping destination with wonderful regency buildings and beautiful flower beds and …see more

from $96 / night

$428 / week

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from $96 / night

(59) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $141 / night

$702 - $893 / week

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avg. 1 hour 34 minutes

from $141 / night

(6) Excellent 

11

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • 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 $229 / night

$1,399 / week

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from $229 / night

(3) Very Good 

22

Charlton Kings Vacation studio rental

Cheltenham / Charlton Kings

Studio 2 2 nights min

  • Studio
  • sleeps 2
  • 2 nights 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 centre(10m …see more

from $58 / night

$402 / week

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avg. 1 hour 9 minutes

from $58 / night

23

Cheltenham Vacation apartment rental

Cotswolds / Cheltenham

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Car not necessary
This newly renovated flat is in a beautiful grade 2* listed building in a quiet and peaceful area, yet within 5 minutes walk of Montpellier, with its array of small shops, independent restaurants and bars. The apartment is perfectly located for the Cheltenham Literature …see more

from $179 / night

$1,174 - $1,531 / week

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Responds fast!
avg. 20 minutes

from $179 / night

(16) Excellent 

Certificate of Excellence

21

Home rental in Prestbury

Cheltenham / Prestbury

6 16 min stay varies

  • 6 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
***** Weekenders - 3 night rates slightly more than 2 nights, contact us ***** 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 …see more

Certificate of Excellence

from $702 / night

$5,101 - $12,753 / week

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Responds fast!
avg. 1 hour 1 minutes

from $702 / night

(5) Excellent 

19

Vacation apartment in Montpellier suburb

Cheltenham / Montpellier suburb

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child 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 the re …see more

from $230 / night

$1,404 - $1,787 / week

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from $230 / 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 $127 / night

$766 - $1,123 / week

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from $127 / night

(8) Excellent 

28

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
  • Private garden
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 $96 / night

$670 / week

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Responds fast!
avg. 2 hours 3 minutes

from $96 / night

(18) Excellent 

29

Vacation townhouse in Pittville

Cheltenham / Pittville

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
10 MINS WALK TO RACES...We would like to invite you to book some quality time at our stunning, refurbished, period property, enjoying all that Cheltenham and the Costwolds have to offer! Leave your car behind and walk to the centre of the town in 10mins, or in the oppos …see more

from $153 / night

$1,072 / week

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Responds fast!
avg. 2 hours 54 minutes

from $153 / night

(5) Very Good 

6

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 been v …see more

from $103 / night

$447 / week

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Responds fast!
avg. 3 hours 33 minutes

from $103 / 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 $181 / night

$1,001 / week

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from $181 / night

(5) Very Good 

9

Vacation b&b in Cheltenham

Cotswolds / Cheltenham

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
This beautifully presented family run Bed and Breakfast is located in the picturesque country side of Cheltenham with views looking across the lower Cotswolds to the Famous Cheltenham Race Course. Situated at the bottom of Cleeve Hill we have 4 large rooms that we let …see more

from $128 / night

$829 - $3,641 / week

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from $128 / night

(2) Good 

29

Vacation cottage in Charlton Kings

Cheltenham / Charlton Kings

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The elegant Regency Spa Town of Cheltenham is located on the western boundaries of the Cotswolds seven miles east of Gloucester and within easy reach of the M5. It is a bustling popular shopping destination with wonderful regency buildings and beautiful flower beds and …see more

from $115 / night

$536 / week

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from $115 / night

13

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Car not necessary
Fabulous modern, interior designers own apartment. 2 bedrooms, 2 double beds, stylish self catering in Cheltenham town centre. The apartment is 1.2 miles from the race course (20 minutes walk) and just a minute or two walk from town centre shops, restaurants, cafes, bar …see more

from $153 / night

$1,072 / week

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Responds fast!
avg. 16 minutes

from $153 / night

(13) Very Good 

8

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 $191 / night

$747 - $1,104 / week

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Responds fast!
avg. 2 hours 39 minutes

from $191 / night

(5) Excellent 

Certificate of Excellence

16

Vacation home rental

Cotswolds / Cheltenham

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Child friendly
  • Private garden
Contemporary-decorated period house very close to Montpellier Square, the Suffolks (Daffodil, Retreat, Beehive), to town centre, restaurants and nightlife. Perfectly situated for Cheltenham Racecourse and Festivals (68 days) - Literature, Jazz, Science, Music, Cricket . …see more

Certificate of Excellence

from $211 / night

$1,212 / week

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Responds fast!
avg. 1 hour 39 minutes

from $211 / night

(3) Excellent 

27

Cheltenham Vacation apartment rental

Cotswolds / Cheltenham

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly
Spacious and comfortable 2 bedroom apartment within easy walking distance of Montpellier Gardens, the town centre and The Promenade with its boutique shops, coffee shops, bars & restaurants. The accommodation offers well equipped kitchen/diner, living room with flat scr …see more

from $127 / night

$885 / week

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from $127 / night

(3) Very Good 

28

Charlton Kings Vacation apartment rental

Cheltenham / Charlton Kings

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Private garden
You'll love my place because it's new, well equipped, warm, quiet and comfortable. It's located within five minutes walking distance from the local shops, pubs and restaurants of Charlton Kings. It's a short drive into the beautiful Cotswold countryside. Five minutes dr …see more

from $64 / night

$383 / week

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Responds fast!
avg. 2 hours 37 minutes

from $64 / night

(1) Excellent 

17

Apartment rental in Cheltenham with golf nearby

Cotswolds / Cheltenham

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
The apartment is located within easy driving distance from the town centre, and is a stunning period apartment with private entrance adjoining this glorious Manor House. Set in a semi rural elevated position it enjoys fantastic views across Cheltenham and the surroundin …see more

from $179 / night

$1,021 / week

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from $179 / night

(29) Excellent 

34

Home rental in Montpellier suburb

Cheltenham / Montpellier suburb

5 9 min stay varies

  • 5 bedrooms
  • sleeps 9
  • min stay varies
  • Child friendly
  • Private garden
Experience the elegance of Regency living - with 21st century comforts in Cheltenham in this magnificently refurbished Regency terraced house in the heart of the cultural capital of England. Following a two year refurbishment this townhouse showcases the latest in sus …see more

from $552 / night

$4,723 / week

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from $552 / night

(15) Excellent 

Certificate of Excellence

14

Vacation studio in Cheltenham

Cheltenham / Cheltenham

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
IN THE HEART OF THE COTSWOLDS Self catering studio apartment with all mod cons., built and furbished in 2012 in the Cotswold village of Woodmancote. Immediate area has thatched cottages, old pubs serving meals, and many beautiful footpaths. Apartment is at the foot of …see more

Certificate of Excellence

from $76 / night

$377 / week

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Responds fast!
avg. 3 hours 51 minutes

from $76 / night

(3) Very Good 

16

Home rental in Cheltenham

Cotswolds / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 30 mi
  • Car not necessary
  • Private garden
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, this uniqu …see more

from $96 / night

$536 / week

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Responds fast!
avg. 1 hour 22 minutes

from $96 / night

(6) Very Good 

16

Vacation cottage in Cheltenham

Cotswolds / Cheltenham

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • 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 $134 / night

$702 - $766 / week

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from $134 / night

(6) Very Good 

20

Vacation apartment in Prestbury

Cheltenham / Prestbury

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • 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 $153 / night

$638 - $1,352 / week

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Responds fast!
avg. 3 hours 55 minutes

from $153 / night

(4) Excellent 

17

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • 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 large French double ( or 2 singles) daybed in the sitting room , a large country kitchen/diner …see more

from $204 / night

$1,021 / week

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Responds fast!
avg. 2 hours 16 minutes

from $204 / night

(1) Excellent 

13

Cheltenham Vacation apartment rental

Cheltenham / Cheltenham

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Car not necessary
This beautiful three bedroom apartment, is in a prime location right next to the promenade, and Montpelier with its' abundance of designer shops, restaurants and pavement cafes.It boasts great views of the town centre, from 3 stories high, boasting large sash windows ar …see more

from $377 / night

$1,786 / week

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from $377 / night

9

Vacation home rental

Cotswolds / Cheltenham

6 18 min stay varies

  • 6 bedrooms
  • sleeps 18
  • min stay varies
  • Child 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 $1,594 / night

$7,652 / week

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Responds fast!
avg. 1 hour 11 minutes

from $1,594 / 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 $192 / night

$1,110 / week

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from $192 / night

29

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
Part of this beautifully restored Grade II listed building the Montpellier Apartment offers you space and luxury in Cheltenham's most fashionable location overlooking Montpellier Gardens. Furnished with beautiful antiques and artworks, with all the 21st century comfort …see more

from $415 / night

$3,830 / week

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from $415 / night

29

Cottage rental in Charlton Kings

Cheltenham / Charlton Kings

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The elegant Regency Spa Town of Cheltenham is located on the western boundaries of the Cotswolds seven miles east of Gloucester and within easy reach of the M5. It is a bustling popular shopping destination with wonderful regency buildings and beautiful flower beds and …see more

from $96 / night

$428 / week

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from $96 / night