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

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Cheltenham

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1,369 Holiday homes

(46) 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

£1,650 - £2,850 / week

Book View

Booked 100+ times!

from £300 / night

(15) 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 £160 / night

£795 - £1,600 / week

Book View

Responds fast!
avg. 3 hours 1 minutes

Booked 40+ times!

from £160 / 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.

from £90 / night

£490 - £590 / week

Book View

Responds fast!
avg. 3 hours 4 minutes

Booked 20+ times!

from £90 / night

(3) 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

Book View

Booked 10+ times!

from £99 / 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

Book View

Booked 6 times

from £75 / 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 £35 / night

£300 / week

Book View

Responds fast!
avg. 2 hours 37 minutes

Booked 6 times

from £35 / 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

Book View

Responds fast!
avg. 3 hours 4 minutes

Booked 8 times

from £65 / night

(57) 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 £125 / night

£550 - £700 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

Booked 100+ times!

from £125 / night

8

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

2 4 Min stay varies

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

from £99 / night

£600 - £880 / week

Book View

from £99 / 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

from £65 / night

£325 / week

Book View

Responds fast!
avg. 3 hours 4 minutes

Booked 30+ times!

from £65 / night

(5) Excellent 

19

Holiday barn in Cheltenham

Cotswolds / Cheltenham

1 2 3 nights min

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

from £122 / night

£485 - £613 / week

Book View

Booked 7 times

from £122 / night

(3) Very Good 

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

Book View

Responds fast!
avg. 1 hour 3 minutes

Booked 30+ times!

from £45 / 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

£650 - £830 / week

Book View

Responds fast!
avg. 3 hours 4 minutes

Booked 30+ times!

from £115 / 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

Book View

Responds fast!
avg. 2 hours 13 minutes

Booked 10+ times!

from £75 / 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

Book View

Booked 10+ times!

from £142 / night

23

Cheltenham holiday apartment rental

Cotswolds / Cheltenham

2 4 Min stay varies

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

from £100 / night

£920 - £1,200 / week

Book View

Responds fast!
avg. 20 minutes

from £100 / 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 could have used the garden.

from £180 / night

£1,100 / week

Book View

Booked 10+ times!

from £180 / 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 £432 / night

£3,700 / week

Book View

Booked 3 times

from £432 / 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

Book View

Responds fast!
avg. 16 minutes

from £120 / night

(5) Excellent 

Certificate of Excellence

16

Holiday home rental

Cotswolds / Cheltenham

3 5 Min stay varies

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

Certificate of Excellence

from £165 / night

£950 / week

Book View

Responds fast!
avg. 1 hour 39 minutes

Booked 10+ times!

from £165 / 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

Book View

Responds fast!
avg. 3 hours 4 minutes

Booked 20+ times!

from £60 / 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

Book View

Booked 9 times

from £180 / 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 £1,350 / night

£4,000 - £11,800 / week

Book View

from £1,350 / night

(20) 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

Book View

Booked 6 times

from £45 / night

(15) 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. 59 minutes

Booked 20+ times!

from £550 / 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 £150 / night

£870 / week

Book View

Booked 3 times

from £150 / 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

Book View

from £99 / 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 quiet holiday stay.” Lovely little unit on a farm. The owners are a lovely family and helped out with anything we needed. Car would be needed at this accommodation.

from £95 / night

£425 - £495 / week

Book View

Responds fast!
avg. 2 hours 25 minutes

from £95 / 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

Book View

Responds fast!
avg. 3 hours 39 minutes

Booked 20+ times!

from £120 / night

(18) Excellent 

29

Holiday townhouse in Pittville

Cheltenham / Pittville

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly

from £120 / night

£840 / week

Book View

Booked 30+ times!

from £120 / night

(13) 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

from £149 / night

£585 - £865 / week

Book View

Responds fast!
avg. 2 hours 17 minutes

Booked 20+ times!

from £149 / 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
“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

Book View

Responds fast!
avg. 8 minutes

Booked 20+ times!

from £65 / night

12

Holiday home in Cheltenham

Cheltenham / Cheltenham

3 4 7 nights min

  • 3 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden

from £100 / night

£575 / week

Book View

Responds fast!
avg. 2 hours 25 minutes

from £100 / night

(4) Excellent 

17

Holiday apartment in Cheltenham

Cotswolds / Cheltenham

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Car not necessary
  • Private garden

from £150 / night

£750 / week

Book View

Responds fast!
avg. 2 hours 55 minutes

Booked 10+ times!

from £150 / night

9

Holiday home rental

Cotswolds / Cheltenham

6 18 Min stay varies

  • 6 bedrooms
  • Sleeps 18
  • Min stay varies
  • Child friendly
  • Private garden

from £1,250 / night

£6,000 / week

Book View

Responds fast!
avg. 1 hour 12 minutes

Booked 3 times

from £1,250 / night

(4) Excellent 

6

Holiday barn in Cheltenham

Cheltenham / Cheltenham

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min

from £80 / night

£350 / week

Book View

Responds fast!
avg. 3 hours 33 minutes

Booked 10+ times!

from £80 / 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

from £75 / night

£420 / week

Book View

Responds fast!
avg. 1 hour 0 minutes

Booked 7 times

from £75 / night

(15) Excellent 

Certificate of Excellence

14

Holiday studio in Cheltenham

Cheltenham / Cheltenham

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Child friendly

Certificate of Excellence

from £59 / night

£295 / week

Book View

Responds fast!
avg. 3 hours 59 minutes

Booked 30+ times!

from £59 / night

(8) Excellent 

34

Cheltenham holiday apartment rental

Cheltenham / Cheltenham

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Private garden

from £140 / night

£900 - £1,040 / week

Book View

Responds fast!
avg. 1 hour 22 minutes

Booked 10+ times!

from £140 / night

13

Holiday home accommodation

Cheltenham / Cheltenham

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden

from £200 / night

£600 / week

Book View

Responds fast!
avg. 2 hours 25 minutes

from £200 / 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

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
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
Cottage Cleeve Common
A fabulous away from it all place, which is actually not far away at all!

We had a brilliant week with our children and grandchildren. The location is magical with the hills and common just outside the front door, enticing us all out to walk and scramble about. The garden is huge and fun to explore, with lovely furniture, but unfortunately we couldn't make use of it as the weather didn't allow it. The house is large and comfortable and we enjoyed spending time in it - we loved the Aga to cook on and dry off our rainy clothes. Comfy beds, lots of space, well equipped kitchen and living areas - all we could ask for and more. Thank you Lynda for such a wonderful holiday home.see more
Beehive Cottage
Great weekend away

Two adults and two children plus rather large dog stayed at beehive cottage. The cottage was in a really convenient place within walking distance to restaurant / pub which was lovely (dog friendly too). The cottage was well appointed although compact but easily accommodated us all. Large king size bedroom and a twin room. Kitchen and living room with everything you need. Toilet seat was broken which we reported and tap was missing from bath which meant the children needed to use shower rather than bath. Very close 15 minutes to Bourton on the Water and Winchcombe for a lovely walk. Also close to Montpellier Terrace /promenade which was great for restaurants and shopping.see more
Stylish Cheltenham ALL YEAR POOL(26-30C) & hot tub
Amazing house

We had a great stay. The house is beautiful and the pool and hot tub were an added bonus. Really enjoyed it and would 100% come back. … see more
King's Cottage, perfect for Cheltenham & Cotswolds
Lovely Cheltenham House

Great location. Attached to good pub with excellent food and drink. A bit squashed for 6 adults, but very comfortable and clean. … see more