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

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1,495 Holiday homes

(51) 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
“Beautiful property with incredible stunning views” Bushcombe House Farm is a beautiful property in a peaceful location with incredible stunning views, obviously a lot of love and attention to detail has gone into this property and it has everything that you could wish for and truly is a most wonderful place to stay. The location is within easy reach of all shops and amenities and a short walk uphill to Cleeve Common. We thoroughly enjoyed our stay and didn't want to leave and we are hoping to return soon. Thank you Peter & Lyn.

from £300 / night

£1,550 - £2,000 / week

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from £300 / 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

from £115 / night

£750 - £820 / week

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from £115 / night

(14) Very Good 

19

Holiday cottage with golf nearby in Cheltenham

Cotswolds / Cheltenham

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly

from £75 / night

£350 - £390 / week

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from £75 / night

(2) 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

from £140 / night

£833 / week

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from £140 / night

(8) 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 £65 / night

£330 - £550 / week

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from £65 / night

(22) 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

from £170 / night

£850 - £1,650 / week

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Responds fast!
avg. 1 hour 50 minutes

from £170 / night

(6) Very Good 

16

Holiday cottage in Cheltenham

Cotswolds / Cheltenham

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly

from £90 / night

£500 - £650 / week

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from £90 / night

(3) Excellent 

16

Cheltenham holiday apartment rental

Cotswolds / Cheltenham

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Car not necessary

from £100 / night

£600 / week

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Responds fast!
avg. 3 hours 13 minutes

from £100 / night

(63) 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
“Idyllic!” Stayed at the Dovecot with my husband and 1 year old daughter. The property itself is beautiful - full of character and very well furnished. The location too is fantastic, right on a duck pond (safely fenced off for little ones) which my daughter loved. The property is a separate building on the owners farm (far away enough from the main building for privacy) - there are horses on the farm which in the evening came up close to the property (still fenced off though) which was lovely. We felt very well looked after by the owners - plenty of information on local attractions was provided, and best of all, a home made chocolate cake waiting for us when we arrived! Having forgotten our high chair, the owner lent us her own which was much appreciated. Location wise - we had a car, which was necessary for what we wanted to do - although I think there were probably plenty of walks in the area. We visited Tewkesbury which was VERY close), Cheltenham, Stow-on-the Wold and Bourton-on-the-Water all very easily from our base. Would definitely stay here again - and probably for a longer period of time.

Certificate of Excellence

from £100 / night

£550 - £700 / week

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Responds fast!
avg. 2 hours 23 minutes

from £100 / night

(4) 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

42

Southam holiday home rental

Cheltenham / Southam

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Child friendly

from £750 / night

£3,600 - £6,370 / week

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from £750 / 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 £1,300 / night

£4,000 - £11,800 / week

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from £1,300 / night

(3) Very Good 

13

Holiday cottage letting

Cotswolds / Cheltenham

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child friendly

from £65 / night

£350 - £390 / week

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from £65 / 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

from £500 / night

£3,500 / week

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from £500 / night

(6) Excellent 

11

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Private garden

from £180 / night

£1,100 - £1,200 / week

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from £180 / night

(10) Excellent 

20

Holiday cottage with golf nearby in Charlton Kings

Cheltenham / Charlton Kings

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly

from £100 / night

£550 - £630 / week

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Responds fast!
avg. 2 hours 22 minutes

from £100 / 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

from £142 / night

£785 / week

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from £142 / night

20

Holiday cottage in Shurdington

Cheltenham / Shurdington

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Child friendly
  • Pet friendly

from £62 / night

£433 - £898 / week

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from £62 / night

(3) Very Good 

28

Charlton Kings holiday apartment rental

Cheltenham / Charlton Kings

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Private garden

from £50 / night

£300 / week

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Responds fast!
avg. 2 hours 19 minutes

from £50 / night

(1) Very Good 

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

(5) Very Good 

6

Holiday barn in Cheltenham

Cheltenham / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

from £80 / night

£350 / week

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Responds fast!
avg. 2 hours 38 minutes

from £80 / 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 - £2,386 / week

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from £180 / night

13

Cheltenham holiday apartment rental

Cotswolds / Cheltenham

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
  • Pet friendly

from £60 / night

£300 / week

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Responds fast!
avg. 1 hour 2 minutes

from £60 / 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

from £75 / night

£335 / week

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Responds fast!
avg. 3 hours 51 minutes

from £75 / night

13

Cleeve Hill holiday home rental

Cheltenham / Cleeve Hill

2 2 7 nights min

  • 2 bedrooms
  • sleeps 2
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £50 / night

£345 - £1,114 / week

Enquire View

from £50 / night

(3) Very Good 

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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Responds fast!
avg. 3 hours 51 minutes

from £90 / night

(1) Excellent 

13

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies

from £100 / night

£600 - £1,250 / week

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Responds fast!
avg. 2 hours 19 minutes

from £100 / night

(8) Excellent 

28

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly
  • Private garden

from £75 / night

£525 / week

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Responds fast!
avg. 2 hours 44 minutes

from £75 / 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

(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

Certificate of Excellence

from £800 / night

£4,000 - £10,000 / week

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Responds fast!
avg. 1 hour 55 minutes

from £800 / night

16

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

4 6 2 nights min

  • 4 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly

from £110 / night

£750 - £1,450 / week

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Responds fast!
avg. 2 hours 54 minutes

from £110 / night

30

Holiday cottage in Charlton Kings

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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Responds fast!
avg. 3 hours 51 minutes

from £75 / night

22

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Car not necessary

from £70 / night

£490 / week

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Responds fast!
avg. 3 hours 1 minutes

from £70 / 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

from £145 / night

£870 / week

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from £145 / 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

20

Holiday home in Charlton Kings

Cheltenham / Charlton Kings

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Child friendly

from £270 / night

£995 - £2,360 / week

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from £270 / night

(5) Very Good 

9

Holiday b&b in Cheltenham

Cotswolds / Cheltenham

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £100 / night

£650 - £2,855 / week

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Responds fast!
avg. 3 hours 41 minutes

from £100 / night

(22) Excellent 

Certificate of Excellence

20

Cheltenham holiday barn rental

Cotswolds / Cheltenham

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
  • Private garden
“A wonderful location away from everything - perfect for family get togethers.” My husband and I and our two children stayed at Southwold Barn for a week in August. We invited along all the grandparents also. There was plenty of room for us all and the barn was extremely well catered for...even down to books and board games should you require any further entertainment. We ate in every evening and even made use of the BBQ too. The kitchen was very well stocked and there was everything that you could ever need. Great that we had the use of wifi and the TV's were great also. Emma (who lives next door) was extremely helpful whenever we had any queries and very understanding when we explained our two year old daughter had attempted to paint her nails but instead had painted the duvet! Emma also welcomed us with an amazing lemon drizzle cake. We visited a different place everyday. My favourites would be Adam Henson's Cotswold Farm, Circencester and Burton on the water. There are lovely pubs nearby Garniche and one in North Leach called the wheat sheaf. Great food here and some wonderful walks. We also visited Chedworth Roman Villa which is run by the National Trust. All in all a fabulous relaxing holiday. Did I mention that we loved Mack the peacock, Rosie the duck and her ducklings, the sheep, hens and the cockerel! A fantastic holiday you won't be disappointed!

Certificate of Excellence

from £45 / night

£536 - £2,040 / week

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from £45 / night

(22) 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
“UNRIVALLED” Our group has stayed in this apartment for the Cheltenham races over the last 7 years or so and to a man would never consider staying anywhere else in the Town.It is ideally located for the Town centre and racecourse and has many other local attractions. The apartment is beautifully decorated and spotlessly clean and the icing on the cake is the fact that the owners are just about the most hospitable and friendly people we have ever encountered on our travels to the extent that they even invite us up on our last day for a Champagne breakfast. Believe me when i say that this accomodation and its owners will guarantee you a fantastic break.

from £65 / night

£455 / week

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Responds fast!
avg. 19 minutes

from £65 / night

12

Cheltenham holiday home rental

Cotswolds / Cheltenham

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly

from £100 / night

£700 - £840 / week

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from £100 / 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

Coach House (Hawling)
Peace and quiet in the Cotswolds

The Coach House in Hawling was such a peaceful place to stay. Set in the grounds of the Old Rectory (yet with personal seclusion), the outlook was over fields and trees. Total silence and darkness for star gazing at night - the Milky Way was unobscured by light pollution. The cottage itself was full of charm and character, whilst decorated to a high quality. The welcome hamper was a nice touch. Easily accessible to the Slaughters, Winchcombe, Cheltenham, Stow and Bourton on the Water. Would definitely recommend.see more
Beehive Cottage
Very very nice, clean property and a perfect base to see the Cotswolds

We (4 adults) thoroughly enjoyed our stay in this property. Not the largest property for a holiday but we found there was enough room for our requirements. Would not hesitate to recommend this property to my friends … see more
St Luke's 1 Bed Apartment
Excellent

Very clean, homely and new property. Would highly recommend. Only stoped for 1 night but very comfortable. Nearby pubs and restaurants. … see more
Bushcombe House Farm Bushcombe Lane Woodmancote
Excellent

This is the second time we have stayed at Bushcombe Lane and it is perfect. The house is very comfortable and clean and the views are stunning! … see more
The Dovecote
Dovecote holiday

What a beautiful, clean, quiet location highly recommended definitely on our list to visit again, owner was super welcoming and helpful. … see more
Spacious and comfortable apartment within walking distance of the town centre
Amazing property

Amazing property, clean, tidy, lovely decor. Great location. Perfect for a weekend with friends. Would highly recommend. Hope to visit again when we’re next in Cheltenham. … see more

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