Holiday rentals near Littledean Jail

We found 1,261 holiday rentals — enter your dates for availability

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November 2025

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Choose the right private holiday rental that's close to Littledean Jail. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as a garden and pool. At the end of the day, you'll be sure to find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Littledean Jail

Showing deals for:30 Jan - 6 Feb

Exceptional

(10 reviews)

The Little House, Luxury Cotswolds Stunning Views

Cheltenham, England

9% off

for 7 nights, 1 home

AU$369 per night

includes taxes & fees

Exceptional

(17 reviews)

Luxury 2 bedroom cottage overlooking the River Wye

Ross-on-Wye, England

21% off

for 7 nights, 1 cottage

AU$208 per night

includes taxes & fees

Exceptional

(41 reviews)

Forest of Dean Romantic & Rustic Holiday Cottage

Lydney, ENG

7% off

for 7 nights, 1 cottage

AU$234 per night

includes taxes & fees

Exceptional

(7 reviews)

(105) Beautiful Stable Cottage in Landmark Grade II Listed Georgian House -

Stroud

28% off

for 7 nights, 1 cottage

AU$249 per night

includes taxes & fees

Exceptional

(45 reviews)

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

Dursley, England

9% off

for 7 nights, 1 home

AU$325 per night

includes taxes & fees

Exceptional

(12 reviews)

Stunning Cotswold Contemporary House set in the vineyards of Woodchester Valley

Stroud, England

18% off

for 7 nights, 1 home

AU$1,296 per night

includes taxes & fees

Exceptional

(131 reviews)

The Apple Store, Great Doward In The Wye Valley

Ross-on-Wye, herefordshire

9% off

for 7 nights, 1 cottage

AU$194 per night

includes taxes & fees

Exceptional

(15 reviews)

Delightful cottage set in the pretty village of Clearwell, Forest of Dean.

Coleford, ENG

8% off

for 7 nights, 1 cottage

AU$270 per night

includes taxes & fees

Exceptional

(5 reviews)

Pet friendly 'Home from Home in the Wye Valley Wales

Chepstow, Wales

9% off

for 7 nights, 1 cottage

AU$244 per night

includes taxes & fees

Exceptional

(176 reviews)

🌿 Peaceful & Cosy Cottage Stay in the Forest of Dean 🌳🐑

Lydney, Gloucestershire

9% off

for 7 nights, 1 cottage

AU$162 per night

includes taxes & fees

Exceptional

(74 reviews)

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

Dursley, DURSLEY

24% off

for 7 nights, 1 home

AU$3,413 per night

includes taxes & fees

Exceptional

(11 reviews)

A rural house on the edge of the Forest of Dean with 3 pubs within a short walk.

Lydney, Gloucestershire

9% off

for 7 nights, 1 home

AU$191 per night

includes taxes & fees

Exceptional

(93 reviews)

Charming, historic mill close to the Cotswold Way in North Nibley<br>

Dursley, England

13% off

for 7 nights, 1 home

AU$810 per night

includes taxes & fees

Exceptional

(51 reviews)

Old Tump House - Cottage With Views Of Forest Of Dean

Blakeney, England

9% off

for 7 nights, 1 cottage

AU$312 per night

includes taxes & fees

Exceptional

(85 reviews)

Beautiful rural retreat; 360 degree views; family-friendly

Hereford, England

20% off

for 7 nights, 1 cottage

AU$209 per night

includes taxes & fees

Exceptional

(12 reviews)

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

Stroud, England

8% off

for 7 nights, 1 room

AU$507 per night

includes taxes & fees

Exceptional

(144 reviews)

Truly STUNNING VIEWS at " beautiful Cotswold cottage" in AONB, Cotswolds England

Stroud, Gloucestershire

9% off

for 7 nights, 1 cottage

AU$382 per night

includes taxes & fees

Exceptional

(55 reviews)

Luxury Self Catering Cottage in Historic Village Setting in the Forest of Dean

Coleford

23% off

for 7 nights, 1 cottage

AU$336 per night

includes taxes & fees

Exceptional

(61 reviews)

Spacious Eco, Pet Friendly Apartments, Forest of Dean, Wye Valley

Lydney, ENG

9% off

for 7 nights, 1 apartment

AU$147 per night

includes taxes & fees

Exceptional

(73 reviews)

A terraced mews cottage close to the banks of the River Wye with beautiful views

Ross-on-Wye, ENG

14% off

for 7 nights, 1 cottage

AU$213 per night

includes taxes & fees

Exceptional

(27 reviews)

The Queens Apt stylish + Free Parking. Hop Skip & Jump to Restaurants

Cheltenham, ENG

9% off

for 7 nights, 1 apartment

AU$613 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Littledean Jail

Spacious Eco, Pet Friendly Apartments, Forest of Dean, Wye Valley

Sleeps 4 · 2 bedrooms · 1 bathroom

Premier Host

Luxury 6 Bed House, Hot Tub, Games Room and in Walking Distance to Village Pub

Sleeps 17 · 6 bedrooms · 3+ bathrooms

Premier Host

Country Cottage With Truly Amazing Views Over The River Wye valley. Pet friendly

Sleeps 4 · 2 bedrooms · 1 bathroom

Premier Host

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

Sleeps 26 · 9 bedrooms · 7 bathrooms

Living room with wall mounted smart tv connected to sky

Amazing location large spacious 3 storey Georgian listed building sleeps 15

Sleeps 15 · 5 bedrooms · 3 bathrooms

Top rated rentals - Littledean Jail

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

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

Swallows Rest beautiful spacious barn conversion

Premier Host

Beautiful location

This property was everything we needed and so much more. If we didn't live so far away (Australia) we would be back. It's the best!

Carol Poole

Stayed Oct 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

A lovely gem

A fabulous place, exceeded our expectations spacious and comfortable. Breakfast cereals and other goodies were an unexpected bonus we really appreciated. Loved our stay

Pam A.

Stayed Oct 2023

Beautiful little cottage

My husband and I loved this gorgeous little cottage. Lovely little welcome basket! Everything was clean and tidy. We would definitely stay again 😊

Maz C.

Stayed Mar 2023

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