50 Best Cheltenham Apartments on Holiday Lettings - Estates

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Cheltenham
16 properties
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14 properties
Montpellier suburb
8 properties
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5 properties

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128 Vacation rentals

(10) Excellent 

12

Vacation chalet rental

Cheltenham / Charlton Kings

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $123 / night

$516 / week

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from $123 / night

(12) Excellent 

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 $207 / night

$968 - $2390 / week

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from $207 / night

(33) 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 $323 / night

$2063 - $2580 / week

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from $323 / 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 $184 / night

$1013 / week

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from $184 / 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 $207 / night

$1220 - $1761 / week

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from $207 / night

(12) Excellent 

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
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 $710 / night

$5160 - $9030 / week

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Responds fast!
avg. 1 hour 4 minutes

from $710 / night

(4) 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 $65 / night

$375 - $710 / week

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Responds fast!
avg. 3 hours 36 minutes

from $65 / 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 $710 / night

$5345 - $14927 / week

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from $710 / 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 $117 / night

$542 - $633 / week

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from $117 / 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 $97 / night

$678 / week

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Responds fast!
avg. 2 hours 45 minutes

from $97 / 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 $239 / night

$1677 / week

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from $239 / night

14

Vacation home rental

Cheltenham / Pittville

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Albemarle Gate is located on the northern outskirts of the town centre overlooking Pittville Pitch and Putt course. Offering 2 bathrooms plus a downstairs cloakroom, this light and ariy house offers great value for groups working in the area, family reunions, short t …see more

from $194 / night

$903 - $1026 / week

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from $194 / 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 $77 / night

$381 / week

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from $77 / night

8

Vacation studio in Prestbury

Cheltenham / Prestbury

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Car not necessary
A ground floor studio annexe with its own private entrance attached to our modern 3 storey house, situated in a quiet area between Cheltenham racecourse and Pittville Park within a small gated development with secure off road parking. The studio consists of a large sit …see more

from $84 / night

$433 / week

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from $84 / night

(12) 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 $193 / night

$755 - $1419 / week

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from $193 / 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 $91 / night

$633 / week

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from $91 / night

19

Vacation barn in Cheltenham

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • 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 $150 / night

$595 - $839 / week

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from $150 / 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 $194 / night

$1290 - $2116 / week

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Responds fast!
avg. 1 hour 6 minutes

from $194 / 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 $65 / night

$375 - $710 / week

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Responds fast!
avg. 3 hours 36 minutes

from $65 / night

(6) Very Good 

20

Vacation apartment in Prestbury

Cheltenham / Prestbury

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • 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 $194 / night

$710 - $6837 / week

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from $194 / 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 $258 / night

$1226 / week

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from $258 / 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 $194 / night

$1123 - $3251 / week

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from $194 / night

(2) Excellent 

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 $194 / night

$968 / week

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Responds fast!
avg. 12 minutes

from $194 / night

(1) Very Good 

20

Cheltenham Vacation apartment rental

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
In the Centre of Cheltenham's bars, shops and restaurants, our 2 bedroom modern top floor (third floor) flat is in an ideal location. Overlooking Leckhampton in the distance, the balcony provides a pleasant space for relaxing. There are 2 double bedrooms, a bathroom w …see more

from $65 / night

$480 - $1161 / week

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Responds fast!
avg. 2 hours 52 minutes

from $65 / night

(1) Excellent 

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 $162 / night

$1129 / week

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from $162 / 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 $97 / night

$484 - $542 / week

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Responds fast!
avg. 53 minutes

from $97 / 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 $168 / night

$1032 / week

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from $168 / night

(9) 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 $65 / night

$375 - $839 / week

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Responds fast!
avg. 3 hours 36 minutes

from $65 / night

(1) Excellent 

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 comfort …see more

from $110 / night

$639 - $1181 / week

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from $110 / night

31

Vacation home rental

Cotswolds / Cheltenham

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Car not necessary
  • Ask about pets
The House boasts high ceilings and Art Deco furnishings and a seven minute walk from the town centre. There is a sizeable garden with a twelve foot trampoline. The Kitchen is well equip and the rooms are spacious. The dining room table seats six comfortably and the draw …see more

from $258 / night

$1806 / week

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from $258 / night

24

Vacation private room in Charlton Kings

Cheltenham / Charlton Kings

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden
The House is an elegant, high ceiling Regency period property, furnished with Art Deco and antique furnishings. There is a well equipt kitchen and luxurious bathroom with a shower. The house is only a seven minute walk from the centre of town and has shop, takeaway and …see more

from $71 / night

$497 / week

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from $71 / 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 $1419 / night

$7418 - $16448 / week

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from $1419 / night

16

Cleeve Hill Vacation home rental

Cheltenham / Cleeve Hill

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Suitable for children age 5+
  • Pet friendly
  • Private garden
The village of Woodmancote enjoys an enviable location with the Regency Spa town of Cheltenham on its doorstep and a wealth of walking from your front door, with well waymarked paths that will take you across this countryside. With easy access for touring the larger Cot …see more

from $69 / night

$482 - $1332 / week

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from $69 / night

15

Vacation home rental

Cheltenham / Pittville

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
This end of terrace house is situated in a quiet backwater of the town centre and is ideally situated for events at the Racecourse, University and Literature Festival. Street parking is available witha permit supplied by the owner or pay and display car park at the rear …see more

from $194 / night

$903 / week

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from $194 / night

(17) 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 $155 / night

$1084 / week

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from $155 / 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 $117 / night

$710 - $774 / week

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Responds fast!
avg. 2 hours 37 minutes

from $117 / night

(7) Very Good 

Certificate of Excellence

34

Vacation apartment in Cheltenham

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $123 / night

$710 - $1677 / week

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from $123 / night

(2) Excellent 

28

Charlton Kings Vacation apartment rental

Cheltenham / Charlton Kings

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • 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

$452 / week

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Responds fast!
avg. 23 minutes

from $65 / night

22

Vacation apartment rental

Cheltenham / Charlton Kings

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden
The property is an old Castle Grade 11 Listed property and Chapel. It is magnificent Kings and Queens residence dating 1639. Breathtaking grounds, Lovely Bridge and Gardens. Grandeur entrance to the building and flat from the main entrance. Luxury feel. Delightful ga …see more

from $581 / night

$4064 / week

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from $581 / night

(2) 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 centre(10m …see more

from $78 / night

$310 / week

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Responds fast!
avg. 44 minutes

from $78 / night