Holiday rentals near Cheltenham Playhouse

We found 2,335 holiday rentals — enter your dates for availability

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September 2025

October 2025

If you'd like to stay close to Cheltenham Playhouse, take a look at holiday rentals to find the perfect one for your trip. Whether you're staying in a holiday rental with a group or just with your pet, you'll find the amenities that you need and want, which might include a pool and a washer and dryer. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Cheltenham Playhouse

Showing deals for:26 Dec - 2 Jan

Exceptional

(74 reviews)

HEATED OUTDOOR POOL(SEASONAL) /LUXURY HOT TUB -SLEEPS 18 + 8 FAMILIES ONLY

Dursley, DURSLEY

19% off

for 7 nights, 1 home

AU$4,661 per night

includes taxes & fees

Wonderful

(27 reviews)

A charming cottage on the Lower Mill private nature reserve in The Cotswolds

Cirencester, ENG

13% off

for 7 nights, 1 cottage

AU$490 per night

includes taxes & fees

Exceptional

(44 reviews)

Newly converted pigsty with amazing views. One small dog welcome.

Dursley, England

9% off

for 7 nights, 1 home

AU$434 per night

includes taxes & fees

Exceptional

(6 reviews)

Campden Place - 2 Bedroom Home in the Centre of Chipping Campden

Chipping Campden, England

9% off

for 7 nights, 1 apartment

AU$478 per night

includes taxes & fees

Exceptional

(34 reviews)

Spacious, light contemporary barn in a rural environment, Gloucestershire

Gloucester, ENG

9% off

for 7 nights, 1 home

AU$245 per night

includes taxes & fees

Cosy 1 bed unit converted piggery. Patio with chairs and Charcoal BBQ

Exceptional

(14 reviews)

Charming converted Piggery on peaceful Cotswold farm

Gloucester, England

14% off

for 7 nights, 1 home

AU$280 per night

includes taxes & fees

Exceptional

(83 reviews)

Quiet Detached Cottage with Stunning Sunsets, 180 Views from all rooms & patio

Stroud, Gloucestershire

5% off

for 7 nights, 1 cottage

AU$391 per night

includes taxes & fees

throw open the doors and soak up the view...

Exceptional

(41 reviews)

The Annexe, quintessentially English, but with a French/Moroccan flavour.

Chipping Campden, ENG

16% off

for 7 nights, 1 cottage

AU$284 per night

includes taxes & fees

Exceptional

(11 reviews)

Lovely Cotswolds farm house on an award winning vineyard with stunning views

Stroud, England

9% off

for 7 nights, 1 room

AU$849 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Cheltenham Playhouse

Secluded Cottage 5 Minute Walk To Broadway Centre

Sleeps 2 · 1 bedroom

Nethercote House a 6 bedroom traditional stone character property

Premier Host

Beautiful 6 bedroom detached property, a flat 5 minute stroll to centre of town

Sleeps 14 · 6 bedrooms · 3 bathrooms

Your very own detached Cottage with off street parking, cottage garden and Well.

Premier Host

Characterful 16th Century Cottage, off street parking, 2 Min Walk to Village!

Sleeps 5 · 2 bedrooms · 1 bathroom

Top rated rentals - Cheltenham Playhouse

Premier Host

Wonders of Bourton

Love all things and place, great location.Cabin captured us and felt like a quant holiday home that you would want to stay at.Thanks to the host Peter for having such a captivating place.

Gary B.

Stayed June 2025

Premier Host

The Hidden Gem

Phillip has a wonderful property that has old world charm mixed in with modern conveniences.with the Cotsworlds Way on the doorstep there is plenty of exploring to do right from your accommodation. Two very lovely pubs just up & down the road.If you are looking for a place to disconnect - make this place a priority.

Caron H.

Stayed Apr 2025

Premier Host

Amazing property and overall experience

I booked this property many months ago for a pre-Christmas weekend in the Cotswolds with my family. The communication throughout with the owner and then the property manager was excellent and the listing details were totally accurate. The only issues we had were the bed mattresses were a little hard and we couldn't find instructions for recycling, but overall it was an amazing experience and highly recommended.

Sue W.

Stayed Dec 2024

Welcome to 21b The Coach House. Private entrance is off a quiet lane

Premier Host

Absolutely perfect

The Coach House is a perfect place for a couple to retreat to after a wonderful day out on Cheltenham and surrounds.Close to restaurants, cafes, pubs and groceries only minutes away. Quaint, and beautifully appointed, the Coach House offers everything needed for a lovely stay. The best however are the little things that Beth the host has really thought about... organic milk for a cuppa, hot chocolate, a supply of chocolates ( which were wonderful on our hikes), bottled water, makeup wipes, clothes pods etc. Would highly recommend.

Helen F.

Stayed May 2024

Premier Host

Beautiful cottage, close to everything yet quiet

Perfectly positioned and equipped - particularly grateful for the wonderful loaf of bread and marmalade welcoming us on our arrival, graciously provided by our hosts!

Susan W.

Stayed Mar 2024

Premier Host

Fabulous stay

Excellent place to stay. Beautiful cosy accommodation in a beautiful setting with excellent hosts. A great place to stay with good routes to Gloucester. We will be back soon.

Victoria H.

Stayed Apr 2021

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