50 Best Cheltenham Apartments on Holiday Lettings - Estates

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1,313 Vacation rentals

(51) 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 $386 / night

$2,120 - $3,662 / week

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from $386 / night

(8) 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 $84 / night

$424 - $707 / week

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from $84 / night

(6) Very Good 

16

Vacation cottage in Cheltenham

Cotswolds / Cheltenham

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 $116 / night

$643 - $835 / week

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from $116 / 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 $180 / night

$1,071 / week

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from $180 / night

(14) Very Good 

19

Vacation cottage with golf nearby in Cheltenham

Cotswolds / Cheltenham

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 $97 / night

$449 - $501 / week

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from $97 / 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 $148 / night

$964 - $1,054 / week

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from $148 / night

(22) 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 $219 / night

$1,092 - $2,120 / week

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avg. 1 hour 59 minutes

from $219 / night

(2) Excellent 

16

Cheltenham Vacation apartment rental

Cotswolds / Cheltenham

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Car not necessary
A lovely, cosy and peaceful apartment located a 5 minutes (0.8 miles) walk away from Cheltenham promenade with amazing restaurants and shops. It is also a two minute walk to Cheltenham college, cricket festival and within walking distance of the everyman theatre, Chelte …see more

from $77 / night

$449 / week

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Responds fast!
avg. 3 hours 13 minutes

from $77 / night

(3) Very Good 

13

Vacation cottage rental

Cotswolds / Cheltenham

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • 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 $84 / night

$450 - $501 / week

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from $84 / night

(29) Excellent 

34

Home rental in Montpellier suburb

Cheltenham / Montpellier suburb

5 9 1 night min

  • 5 bedrooms
  • sleeps 9
  • 1 night min
  • 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 $643 / night

$4,497 / week

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from $643 / night

42

Southam Vacation home rental

Cheltenham / Southam

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Child friendly
A newly modernised and fully refurbished 5/6 bedroom family home with stunning views over Cheltenham Racecourse. Ideally located for stunning walks and equally if you want to enjoy the buzz of Cheltenham town itself with all its restaurants, bars, exclusive shopping ar …see more

from $962 / night

$4,614 - $8,164 / week

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from $962 / night

(63) 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 $161 / night

$707 - $900 / week

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avg. 2 hours 23 minutes

from $161 / 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 $1,670 / night

$5,139 - $15,160 / week

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from $1,670 / 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 $65 / night

$386 / week

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Responds fast!
avg. 2 hours 19 minutes

from $65 / 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 $128 / night

$891 / week

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from $128 / 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 $231 / night

$1,412 - $3,062 / week

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from $231 / 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 $183 / night

$1,008 / week

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from $183 / 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 $97 / night

$431 / week

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Responds fast!
avg. 3 hours 44 minutes

from $97 / night

(1) Very Good 

23

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly
Lypiatt Terrace is one of the most recognisable terraces in Cheltenham. The spacious and comfortable 2 bedroom apartment is split over two floors and is within easy walking distance of fashionable Montpellier, the town centre and The Promenade with its boutique shops, …see more

from $128 / night

$891 / week

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from $128 / 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 $97 / night

$675 / week

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Responds fast!
avg. 2 hours 44 minutes

from $97 / 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

$450 / week

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Responds fast!
avg. 2 hours 20 minutes

from $103 / 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 $232 / night

$1,414 / week

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from $232 / night

13

Cheltenham Vacation apartment rental

Cotswolds / Cheltenham

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
Located in Cheltenham, 900 yards from Cheltenham Town Hall and 1,000 yards from University of Gloucestershire, Lansdown provides accommodation with amenities such as free WiFi and a flat-screen TV. The property is 0.7 miles from Cheltenham General Hospital. The apartmen …see more

from $93 / night

$514 / week

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Responds fast!
avg. 1 hour 6 minutes

from $93 / night

(10) 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 fabulous shoppin …see more

from $129 / night

$706 - $809 / week

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Responds fast!
avg. 1 hour 46 minutes

from $129 / night

(3) Very 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 $116 / night

$539 / week

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Responds fast!
avg. 3 hours 44 minutes

from $116 / night

22

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Car not necessary
Our first floor apartment is located in the centre of Cheltenham just off The Promenade in Montpellier with easy access to fashionable shops bars and restaurants theatre beautiful architecture and gardens. A ground floor imposing front door and internal staircase lead …see more

from $90 / night

$630 / week

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Responds fast!
avg. 2 hours 43 minutes

from $90 / night

(1) Excellent 

13

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
One of our bestsellers in Cheltenham! This furnished apartment can be found in a prime location in the centre of town, only 300 metres from Cheltenham Town Hall, 420 metres from Cheltenham General Hospital and 500 metres from the shops, pubs and restaurants of Cheltenh …see more

from $129 / night

$771 - $1,606 / week

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Responds fast!
avg. 2 hours 19 minutes

from $129 / 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 $1,028 / night

$5,139 - $12,847 / week

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Responds fast!
avg. 2 hours 10 minutes

from $1,028 / night

28

Apartment rental in Cheltenham

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 fashionable Montpellier, the town centre and The Promenade with its boutique shops, coffee shops, bars & restaurants. The accommodation offers well equipped kitchen, living/dining room with fla …see more

from $110 / night

$765 / week

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from $110 / night

30

Vacation cottage in Charlton Kings

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 $97 / night

$431 / week

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Responds fast!
avg. 3 hours 44 minutes

from $97 / night

16

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

4 6 2 nights min

  • 4 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
A newly refurbished, contemporary styled Apartment. With 4 bedrooms (2 doubles and 2 small doubles), a main bathroom and an en-suite - this Apartment caters easily for 6 persons. Located centrally in Cheltenham, a stones throw from the re-invigorated Brewery Quarter w …see more

from $142 / night

$964 - $1,863 / week

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Responds fast!
avg. 3 hours 7 minutes

from $142 / night

12

Cheltenham Vacation home rental

Cotswolds / Cheltenham

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • 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 $129 / night

$900 - $1,080 / week

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from $129 / 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 $97 / night

$541 / week

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Responds fast!
avg. 1 hour 23 minutes

from $97 / night

20

Vacation home in Charlton Kings

Cheltenham / Charlton Kings

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly
Originally the coach house to the main estate and in later life the gym for a private school, The Coach House Seven Springs is now a beautiful home that will make the ideal getaway to explore both Cheltenham and the Cotswolds. The contemporary finish has been designed t …see more

from $347 / night

$1,277 - $3,029 / week

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from $347 / night

(22) Excellent 

Certificate of Excellence

20

Cheltenham Vacation barn rental

Cotswolds / Cheltenham

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
  • Private garden
Fully accredited by Quality in Tourism (Visit England) as 5* and a Gold Award Winner FOR FULL PRICING SEE OUR WEBSITE SEARCH FOR SOUTHWOLDBARN.CO.UK Southwold Barn sleeps 8 people. On the ground floor, there is a large vaulted drawing room with original stonewor …see more

Certificate of Excellence

from $58 / night

$688 - $2,618 / week

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from $58 / night

(16) 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

$379 / week

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Responds fast!
avg. 3 hours 20 minutes

from $76 / night

26

Vacation home accommodation

Cheltenham / Cleeve Hill

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Child friendly
A beautiful large family home within easy reach of Cheltenham. The property has several balconies so you can enjoy the glorious views of the surrounding countryside. La Folie is situated in an area of outstanding natural beauty, is situated very close to Cheltenham …see more

from $1,348 / night

$6,929 - $17,553 / week

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from $1,348 / night

(1) Excellent 

13

Cheltenham Vacation apartment rental

Cheltenham / Cheltenham

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • 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 $359 / night

$1,799 / week

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from $359 / night

(22) 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 seat. 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 added should this b …see more

from $84 / night

$585 / week

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Responds fast!
avg. 19 minutes

from $84 / 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 $187 / night

$1,118 / week

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from $187 / night