50 Best Cheltenham Apartments on Holiday Lettings - Estates

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Cheltenham
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12 properties
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8 properties
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7 properties
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6 properties

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1,387 Vacation rentals

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 $126 / night

$588 / week

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from $126 / night

(44) 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 $350 / night

$1,750 - $2,800 / week

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from $350 / 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 $1,750 / night

$8,050 - $15,890 / week

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avg. 1 hour 2 minutes

from $1,750 / night

(11) 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 $91 / night

$455 - $910 / week

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from $91 / 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 $168 / night

$700 - $7,420 / week

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from $168 / night

(2) 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 $139 / night

$971 / week

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Responds fast!
avg. 3 hours 35 minutes

from $139 / 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 $280 / night

$1,330 / week

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from $280 / night

13

Vacation cottage rental

Cheltenham / Charlton Kings

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 $84 / night

$392 - $490 / week

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from $84 / night

(3) Very Good 

19

Cottage rental in Charlton Kings

Cheltenham / Charlton Kings

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 $140 / night

$700 - $1,162 / week

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from $140 / 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 $77 / night

$539 / week

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Responds fast!
avg. 1 hour 42 minutes

from $77 / night

(13) 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 $224 / night

$1,113 - $2,240 / week

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Responds fast!
avg. 3 hours 44 minutes

from $224 / night

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 $105 / night

$469 / week

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from $105 / 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 $181 / night

$1,112 / week

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from $181 / night

(5) 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

$406 - $770 / week

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from $84 / night

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 $139 / night

$971 / week

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Responds fast!
avg. 3 hours 35 minutes

from $139 / night

(7) 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 $105 / night

$735 / week

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Responds fast!
avg. 2 hours 48 minutes

from $105 / night

(6) Very Good 

16

Vacation cottage in Charlton Kings

Cheltenham / Charlton Kings

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 $119 / night

$546 - $826 / week

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from $119 / night

(3) Excellent 

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 $163 / night

$646 - $819 / week

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from $163 / 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 $181 / night

$1,112 / week

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from $181 / night

(54) 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 $133 / night

$700 - $1,680 / week

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Responds fast!
avg. 3 hours 32 minutes

from $133 / 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 $251 / night

$1,529 / week

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from $251 / night

(39) Excellent 

24

Vacation apartment in Cheltenham

Cheltenham / Cheltenham

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 35 mi
  • Suitable for children age 5+
  • Car not necessary
Village Mews is a very,very large apartment spanning 2 floors. Accessed via ground floor stairs with exclusive front door.Comfortably furnished,your every comfort is catered. for a relaxing and pleasurable home from home,with no hidded extras. High speed broadband and …see more

from $140 / night

$980 - $2,379 / week

Inquire View

from $140 / night

(4) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from $112 / night

$487 / week

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Responds fast!
avg. 3 hours 1 minutes

from $112 / night

(2) 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 $126 / night

$770 / week

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Responds fast!
avg. 1 hour 37 minutes

from $126 / night

(2) Excellent 

15

Apartment rental in Prestbury

Cheltenham / Prestbury

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • 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 $119 / night

$693 - $2,100 / week

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from $119 / 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 $259 / night

$1,820 / week

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from $259 / night

15

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 $77 / night

$537 - $1,445 / week

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from $77 / night

(7) 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 $140 / night

$770 / week

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from $140 / 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 $105 / night

$735 / week

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Responds fast!
avg. 3 hours 36 minutes

from $105 / night

(12) 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 $133 / night

$770 - $1,960 / week

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from $133 / night

(1) Excellent 

16

Vacation home rental

Cheltenham / Andoversford

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Ask about children
  • Private garden
Our home is a semi detached three bedroom house on three floors. Ground floor: kitchen with dishwasher, washing machine, microwave, grill, oven, five hobs, fridge and fridge freezer. with access to the downstairs WC. Living room with seating for five, free-view and Wi …see more

from $210 / night

$1,554 / week

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Responds fast!
avg. 59 minutes

from $210 / 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 $168 / night

$1,176 / week

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from $168 / 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 $1,400 / night

$5,600 - $14,336 / week

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from $1,400 / 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 $105 / night

$522 / week

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Responds fast!
avg. 47 minutes

from $105 / 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 $630 / night

$4,410 / week

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from $630 / night

(13) 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 $765 / night

$5,560 - $13,900 / week

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Responds fast!
avg. 34 minutes

from $765 / 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 $126 / night

$1,015 - $1,190 / week

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Responds fast!
avg. 2 hours 24 minutes

from $126 / night

(2) Excellent 

30

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 $63 / night

$441 / week

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Responds fast!
avg. 1 hour 27 minutes

from $63 / night

(13) Excellent 

Certificate of Excellence

14

Vacation studio in Cheltenham

Cheltenham / Cheltenham

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Child friendly
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

$378 - $413 / week

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from $76 / 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 $252 / night

$980 / week

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Responds fast!
avg. 2 hours 51 minutes

from $252 / night