50 Best Cheltenham Apartments on Holiday Lettings - Estates

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105 Vacation rentals

(32) 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 $318 / night

$2031 - $2540 / week

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from $318 / night

10

Apartment rental in Montpellier suburb

Cheltenham / Montpellier suburb

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
Croft House is a beautiful, one-bedroom luxury serviced apartment situated in one of the most spectacular Grade II Regency villas in Cheltenham. Spread across the first floor of this striking building, the apartment offers access to two balconies from the open plan loun …see more

from $205 / night

$1210 - $1748 / week

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from $205 / 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 Size …see more

from $204 / night

$1156 - $1207 / week

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from $204 / night

(6) 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

$667 / week

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Responds fast!
avg. 2 hours 44 minutes

from $96 / night

(4) 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 $102 / night

$445 / week

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Responds fast!
avg. 3 hours 21 minutes

from $102 / night

(16) Excellent 

29

Vacation townhouse in Pittville

Cheltenham / Pittville

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
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 $154 / night

$1076 / week

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from $154 / night

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

from $191 / night

$953 / week

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from $191 / night

(6) 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 $231 / night

$1409 / 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 $182 / night

$1005 / week

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from $182 / night

(29) Excellent 

34

Home rental in Montpellier suburb

Cheltenham / Montpellier suburb

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Suitable for children age 5+
  • Ask about pets
  • 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 $699 / night

$5262 - $14696 / week

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from $699 / 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 $64 / night

$372 - $705 / week

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Responds fast!
avg. 2 hours 57 minutes

from $64 / night

(6) Very Good 

Certificate of Excellence

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

Certificate of Excellence

from $121 / night

$699 - $1651 / week

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from $121 / 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 $64 / night

$372 - $705 / week

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Responds fast!
avg. 2 hours 57 minutes

from $64 / night

(3) Very Good 

16

Home rental in Cheltenham

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $87 / night

$477 - $489 / week

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Responds fast!
avg. 49 minutes

from $87 / night

22

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
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 beuriful,architecture and gardens. A ground floor imposing front door and internal staircase lead t …see more

from $90 / night

$628 / week

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from $90 / night

(51) 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 $160 / night

$640 - $1536 / week

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Responds fast!
avg. 3 hours 33 minutes

from $160 / 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 $180 / night

$1076 / week

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from $180 / night

(12) Excellent 

Certificate of Excellence

14

Vacation studio in Cheltenham

Cheltenham / Cheltenham

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Ask about children
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 $75 / night

$375 / week

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from $75 / 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 the re …see more

from $235 / night

$1651 / week

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from $235 / 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 has been renovated to provide excellent accommodation for up to 12 guests. We are dog friendly and welcome your 4-legged family member. The living accommodation is arranged in an open-plan manner - providing a perfect large sociable space for family gath …see more

from $254 / night

$1524 - $3912 / week

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from $254 / night

(12) Very Good 

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 $191 / night

$749 - $1409 / week

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from $191 / 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 communa …see more

from $167 / night

$1024 / week

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from $167 / 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 $166 / night

$907 - $3201 / week

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from $166 / night

23

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 $160 / night

$1120 / week

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from $160 / night

(4) 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 large French double ( or 2 singles) daybed in the sitting room) , a large country kitchen/diner …see more

from $205 / night

$749 - $960 / week

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Responds fast!
avg. 2 hours 31 minutes

from $205 / 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 cares …see more

from $145 / night

$801 - $826 / week

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from $145 / night

(7) 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 $64 / night

$372 - $832 / week

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Responds fast!
avg. 2 hours 57 minutes

from $64 / night

(2) Excellent 

18

Home accommodation in Cheltenham

Cotswolds / Cheltenham

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
A beautiful two bedroom, three storey home with a garden in a quiet area within a five minute walk to the town centre or the spectacular Pittville Park. If you have a car, you're in the middle of the Cotswolds where you can explore beautiful ltiny towns with thatched c …see more

from $167 / night

$1024 / week

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from $167 / 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 $172 / night

$921 - $1080 / week

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Responds fast!
avg. 2 hours 19 minutes

from $172 / night

(1) Excellent 

9

Cheltenham Vacation apartment rental

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
Comfortable one bedroomed flat, plenty of space for travel cot. Very well placed for everything. 5 minutes to centre and all bus services. Approximately one mile from station. Near parks, hospital and all amenities. Rental includes linen and all services. Par …see more

from $102 / night

$699 - $762 / week

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Responds fast!
avg. 2 hours 39 minutes

from $102 / night

(9) 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 $832 / night

$5760 - $8960 / week

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Responds fast!
avg. 2 hours 13 minutes

from $832 / 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 $1270 / night

$5080 - $12589 / week

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from $1270 / night

(3) Very Good 

19

Cottage rental in Charlton Kings

Cheltenham / Charlton Kings

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • 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 $141 / night

$807 - $1088 / week

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Responds fast!
avg. 2 hours 57 minutes

from $141 / night

(6) Excellent 

34

Cheltenham Vacation apartment rental

Cheltenham / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Private garden
Our apartment is comfortable with all you need to make your stay enjoyable, plus a few extras. The two bedroomed garden apartment is part of a period property, well equipped and stylish. Close to the action of Montpellier and the Suffolks, you can enjoy your stay, whet …see more

from $192 / night

$1280 - $2100 / week

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Responds fast!
avg. 1 hour 1 minutes

from $192 / 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 $96 / night

$672 / week

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Responds fast!
avg. 3 hours 26 minutes

from $96 / 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 $1409 / night

$7360 - $16320 / week

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from $1409 / 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 $180 / night

$1255 / week

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from $180 / night

21

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 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 area …see more

from $845 / night

$2560 - $9754 / week

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from $845 / night

4

Staverton Vacation private room rental

Cheltenham / Staverton

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Private garden
The property is in the new build area in beautiful Cheltenham Spa. It has spacious rooms with modern furniture and ensuit. The room is light and the bed is comfortable. The property has large kitchen with dinning area. Walking distance to Montpellier, town centre and an …see more

from $48 / night

$308 / week

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from $48 / night

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

$538 - $628 / week

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from $116 / night

1