Apartments in Cheltenham and Self catering accommodation - Holiday Lettings - Holiday Rentals Cheltenham

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Cheltenham

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1,394 Holiday homes

(14) Excellent 

25

Holiday 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
“SPECTECULAR” first al all, the help we got till we arrived at the house was amazing. lynda and john are the most helpful people out there. nice and relaxed people. the house is big, spacey, comfy and clean. the view is pure breathtaking highly r
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from £160 / night

£795 - £1,600 / week

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Responds fast!
avg. 3 hours 19 minutes

from £160 / night

(2) Excellent 

27

Cheltenham holiday apartment rental

Cotswolds / Cheltenham

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly

from £99 / night

£693 / week

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from £99 / night

(1) Excellent 

5

Holiday home accommodation

Cheltenham / Leckhampton

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly

from £120 / night

£650 / week

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from £120 / night

(4) Excellent 

19

Holiday barn in Cheltenham

Cotswolds / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
“ABSOLUTELY PERFECT, More than we had hoped for!” We had a brilliant stay at Park Bothy, the cabin was incredible clean new homely well equipped and situated in the most beautiful location!! We had the most perfect weekend away, it truly was amazing, I
…see more

from £116 / night

£461 - £585 / week

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from £116 / night

(44) Excellent 

40

Holiday farmhouse in Cheltenham

Cheltenham / Cheltenham

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
“Brilliant house, beautiful location” The house is set is an absolutely stunning location. The views form the garden are beautiful. The house is very well equipped. Plenty of crockery etc (and lots of kids cups, plates etc). The open plan kitchen/diner
…see more

from £300 / night

£1,650 - £2,850 / week

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from £300 / night

(11) Very Good 

19

Holiday cottage with golf nearby in Cheltenham

Cotswolds / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
“Cosy, convenient intro to Cheltenham and the Cotswolds” Situated just off main road to Cheltenham (10 minute drive) so was convenient for me to get to know the town and also to walk footpaths straight from the cottage including the Gloucestershire Way
…see more

from £65 / night

£325 / week

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Responds fast!
avg. 2 hours 33 minutes

from £65 / night

23

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly

from £99 / night

£693 / week

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from £99 / night

(4) Excellent 

Certificate of Excellence

6

Holiday barn in Cheltenham

Cheltenham / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

Certificate of Excellence

from £80 / night

£350 / week

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Responds fast!
avg. 3 hours 7 minutes

from £80 / night

(2) Excellent 

30

Charlton Kings holiday studio rental

Cheltenham / Charlton Kings

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Ask about pets

from £45 / night

£315 / week

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Responds fast!
avg. 1 hour 14 minutes

from £45 / night

(20) Very Good 

12

Holiday apartment rental

Cheltenham / Cheltenham

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Nearest beach 90 km
  • Child friendly
  • Car not necessary
“Fantastic appartment, great location” We had an awesome stay, much of which was down to the owners who could not of been more accommodating. The appartment has everything you could need and more. Local shops/ cafe/ pub etc. and a 5 min walk to Chelte
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from £65 / night

£455 / week

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Responds fast!
avg. 51 minutes

from £65 / night

(20) Excellent 

20

Cheltenham holiday barn rental

Cotswolds / Cheltenham

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Private garden
“Great accommodation for wedding guests” I booked this for 5 adults and 2 children 15 months and 3 years, including my mum who is in her 80's. for 3 nights as guests at our family wedding at Upcote Barn Withigton What a lovely welcome from Emma, and l
…see more

from £220 / night

£985 / week

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from £220 / night

(5) Excellent 

19

Holiday apartment in Montpellier suburb

Cheltenham / Montpellier suburb

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

from £180 / night

£1,100 - £1,400 / week

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from £180 / night

(6) Excellent 

11

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Private garden
“Very comfy. Easy walk into town.” The apartment was very clean and warm, it’s got a lovely lounge with a comfy sofa. It’s a really nice home from home. It had everything we needed to make a great stay. I just wish my stay was in the summer so I cou
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from £180 / night

£1,100 / week

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from £180 / night

(14) Excellent 

23

Cheltenham holiday apartment rental

Cheltenham / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Car not necessary
  • Air conditioning
“A luxury apartment in the heart of Cheltenham” I had a lovely stay in this gorgeous apartment, right where I wanted to be on the Promenade. The accommodation was immaculate, with everything from furnishings to cutlery top notch quality, and the owner
…see more

from £142 / night

£785 / week

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from £142 / night

29

Holiday cottage rental

Cheltenham / Charlton Kings

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Pet friendly

from £75 / night

£335 / week

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from £75 / night

12

Cleeve Hill holiday 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

from £50 / night

£345 - £1,114 / week

Enquire View

from £50 / night

13

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Car not necessary

from £120 / night

£840 / week

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Responds fast!
avg. 10 minutes

from £120 / night

13

Holiday cottage letting

Cotswolds / Cheltenham

1 2 2 nights min

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

from £65 / night

£350 / week

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Responds fast!
avg. 2 hours 33 minutes

from £65 / night

(56) Excellent 

Certificate of Excellence

23

Holiday home rental

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Ask about pets
  • Private garden
“Super little cottage” Positives: Characterful property Lots of Attention to detail Free wi-fi Ideal location Well equipped holiday rental Very clean Tasty Victoria sponge cake awaited us on arrival Helen (owner) extremely help
…see more

Certificate of Excellence

from £125 / night

£550 - £700 / week

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Responds fast!
avg. 2 hours 56 minutes

from £125 / night

(6) Very Good 

16

Holiday cottage in Cheltenham

Cotswolds / Cheltenham

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
“Excellent!” Excellent little cottage for a quick get away and yet close to town. The host was very helpful and kind.
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from £90 / night

£490 - £590 / week

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Responds fast!
avg. 2 hours 33 minutes

from £90 / night

(5) Very Good 

10

Holiday apartment in Montpellier suburb

Cheltenham / Montpellier suburb

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 94 km
  • Child friendly
  • Car not necessary

from £200 / night

£950 / week

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from £200 / 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

from £160 / night

£945 - £1,365 / week

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from £160 / 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 km
  • Car not necessary
  • Private garden
“Excellent stay” Fabulous stay, little hidden gem in cheltenham. Beth (the owner) is lovely and very helpful. Definitely would recommend, and I also plan on going back to stay again. Location - is lovely, very near to shops and local amenities. Litt
…see more

from £75 / night

£420 / week

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Responds fast!
avg. 57 minutes

from £75 / night

13

Cheltenham holiday apartment rental

Cheltenham / Cheltenham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Car not necessary

from £295 / night

£1,400 / week

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from £295 / night

(5) Excellent 

9

Holiday cottage with golf nearby in Cheltenham

Cheltenham / Cheltenham

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly

from £60 / night

£300 - £550 / week

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Responds fast!
avg. 2 hours 33 minutes

from £60 / night

29

Holiday 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

from £90 / night

£420 / week

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from £90 / night

(7) Excellent 

28

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Child friendly
  • Private garden

from £75 / night

£525 / week

Book View

Responds fast!
avg. 2 hours 50 minutes

from £75 / night

(3) Very Good 

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

from £85 / night

£495 - £1,500 / week

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Responds fast!
avg. 2 hours 47 minutes

from £85 / night

(14) Excellent 

Certificate of Excellence

14

Holiday studio in Cheltenham

Cheltenham / Cheltenham

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly
“Highly recommended for anyone!” Our FIRST visit to "TWO Hills View" gave us the opportunity to do THREE car boots in the area and FOUR family-visits. On day FIVE we went to the church in Cheltenham. Day SIX was still sunny and warm. The SEVENTH day we
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Certificate of Excellence

from £59 / night

£295 / week

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from £59 / 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
“Exactly what we wanted” We needed three bedrooms to satisfy two teenagers so the Windrush fitted the bill. The cottage is situated in a beautiful location and because we wanted to visit numerous places in the area is in an ideal location. Very comfort
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from £115 / night

£650 - £830 / week

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Responds fast!
avg. 2 hours 33 minutes

from £115 / night

(5) Excellent 

16

Holiday home rental

Cotswolds / Cheltenham

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Private garden

from £165 / night

£950 / week

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Responds fast!
avg. 1 hour 43 minutes

from £165 / night

13

Holiday apartment in Leckhampton

Cheltenham / Leckhampton

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about pets

from £75 / night

£525 / week

Book View

Responds fast!
avg. 3 hours 8 minutes

from £75 / night

(6) Very Good 

20

Holiday apartment in Prestbury

Cheltenham / Prestbury

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly

from £120 / night

£500 - £1,060 / week

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Responds fast!
avg. 3 hours 13 minutes

from £120 / night

(1) Excellent 

45

Holiday home in Cheltenham

Cotswolds / Cheltenham

7 20 Min stay varies

  • 7 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly
  • Private garden

from £1,250 / night

£4,000 - £10,240 / week

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from £1,250 / night

8

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

from £105 / night

£600 - £880 / week

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from £105 / night

28

Apartment rental in Cheltenham

Cotswolds / Cheltenham

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly

from £85 / night

£595 / week

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from £85 / night

(29) Excellent 

34

Home rental in Montpellier suburb

Cheltenham / Montpellier suburb

5 9 Min stay varies

  • 5 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Private garden

from £750 / night

£4,500 / week

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from £750 / night

(6)  

15

Holiday apartment rental

Cheltenham / Cheltenham

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Child friendly
  • Car not necessary

from £75 / night

£400 - £475 / week

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Responds fast!
avg. 2 hours 24 minutes

from £75 / night

(10) Excellent 

12

Holiday chalet rental

Cheltenham / Charlton Kings

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
“Lovely place for a city/country retreat.” Great little backyard cottage. Close to town but far enough away to get away from it all. Cosy and warm. Owners were lovely!
…see more

from £95 / night

£425 - £475 / week

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Responds fast!
avg. 2 hours 32 minutes

from £95 / night

(14) 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

Certificate of Excellence

from £550 / night

£4,000 - £10,000 / week

Book View

Responds fast!
avg. 32 minutes

from £550 / night

Why Cheltenham?

The Regency town of Cheltenham is perfect for those looking for a sophisticated getaway that's not too far from the rolling hills of the countryside.

Select a holiday rental in Cheltenham, and start planning your trip to one of England's most famous spa towns.

About Cheltenham

Cheltenham's history spans back centuries, and has always been a popular tourist spot thanks to the mineral springs that flow here.

The town itself is on the edge of the Cotswolds and is an area of outstanding natural beauty. Many choose to hike and roam through the hills to check out the views. If you go, don't forget your camera as there are plenty of photo-op spots along the trails.

What to Do

There are galleries, theatres and museums throughout the town, so why not visit one? The Wilson is among the most popular.

Top Cheltenham Travel Tips

Cheltenham is known all over the world for being a hive of culture and excitement. Each year, thousands flock here for the horse racing, jazz, and food & drink festivals. See if you can time your holiday to coincide with one of these. It's well worth it for the atmosphere.

Cheltenham is a wonderful place where you can wander around to your heart's content. Book your holiday rental in Cheltenham and let the adventure begin.

Top Destination reviews

Nethercote Cottage
Wonderful experience

Beautiful cottage everything we needed great location near everything we wanted to see. Great friendly owner highly recommended. … see more
Perfect for festivals, races and Cotswolds access in the centre of Cheltenham
Perfect town break

We booked this for a family celebration get together, combined with the Literary Festival. The location was superb for the Festival, only 5 minutes walk and easy access into the town to get supplies and plenty of restaurants nearby. The house was immaculate throughout and decor is superb. Sue even arranged an on-street parking permit for the extra car. I can thoroughly recommend a stay here and we'd all like to stay there again next year for the Literary Festival if not before.see more
The Dovecote
Dovecote Stay

Thank you Helen for the wonderful stay at the Dovecote. Such a beautiful cottage with everything we needed. A perfect base for exploring the Cotswolds. We will definitely be recommending the Dovecote to all our family and friends. … see more
Bushcombe House Farm Bushcombe Lane Woodmancote
Snow stay!

Excellent cottage. So comfortable and cosy Everything you would need. Great position and so near to Cheltenham centre. Just needed a shovel when the snow came!!! Looked very pretty but we should have taken skis. Would visit again … see more
Prestbury Garden Apartment
Lovely

Lovely apartment in a quiet village. Lovely country pubs very close by. We loved our stay and would definitely return. Only thing was the cleaning wasn't perfect. Bits and bobs on carpets underneath sofa and beds and plates had food residue. Also some bits left in dishwasher so we had to wash up bits to make sure they were washed before using. And lack of large towels. There were 2 for four people? Despite all these little bits we wouldn't hesitate in returning as despite the cleaning it was a beautiful well designed flat with a lot of time spent over the little added features that made it feel special.see more
Park Bothy Barn, NEW BARN CONVERSION.
Absolute bliss

Had a fantastic break away from it all, loved the barn. I took my 2 well travelled dogs and they loved the garden which although isn’t totally fenced off was ideal for them. Great dogs walks within 10 mins. Lovely part of the world. Loved being able to park at the door. So cosy, so peaceful I barely went out. I will be returning. Like the idea of tv in the bedroom too which few places seem to have these days. Although you are next to another barn the way it is positioned you are very private. Highly recommend.see more