Guesthouse holiday rentals in Cheltenham

Find and book unique guesthouse rentals on Airbnb

Top-rated Guesthouses in Cheltenham

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Cheltenham

4.95 out of 5 average rating, 219 reviews

Boutique Cotswold bolt hole - Ford Manor Cottage

Entire cottage set in grounds of owner's home with own gravelled and gated parking area, in the heart of the Cotswolds and National Hunt racing. Luxury open plan living/bedroom (approx. 25 sq m) which is light and airy with 4 post bed , well equipped galley kitchen and wet room. Complete privacy. Ideal retreat for short or long stays. A great base for walking and exploring the Cotswolds, with the Cotswold Way on the doorstep, Sudeley Castle a few miles away and Daylesford a 15 minute drive.

1 – 8 Oct

$1,412 AUD total

Guest favourite

Guesthouse in Leigh

4.92 out of 5 average rating, 155 reviews

Cosy countryside retreat.

The Nest is a self contained detached annexe set in the peaceful Gloucestershire village of The Leigh. The property has been newly refurbished and is available for up to 2 people with access to a secluded garden space within our lovely orchard surroundings. The property has easy access and ample parking. Located within easy reach of Cheltenham, Tewkesbury, Gloucester, The Malverns, Cotswolds and M5, the accommodation is in a perfect position for exploring all that the area has to offer.

21 – 28 Oct

$1,210 AUD total

Guest favourite

Guesthouse in Twyning

4.78 out of 5 average rating, 235 reviews

The groomsroom

Ex - grooms room, in the grounds of a beautiful country mansion. Self contained bedsit/studio with parking. Stabling available at extra cost if you want to turn this into an equine holiday! 4 miles from Tewkesbury and on the outskirts of Twyning, a beautiful location for a country break. Seasonal breakfast ingredients provided, but we are afraid you'll have to cook them yourself! Tea and coffee making facilities also provided. Fresh milk and bread will be in the fridge when you arrive.

30 July – 6 Aug

$629 AUD total

Guest favourite

Guesthouse in Minchinhampton

4.98 out of 5 average rating, 262 reviews

The Cotswolds Couples' Getaway

In the centre of beautiful Minchinhampton, this detached cosy cottage is open plan in design and tastefully renovated throughout with plenty of modern conveniences. Set in our quiet pretty garden, and with on-site parking + Type 2 EV charger, a perfect getaway. The space is safe for a couple, equipped for living, and it is easy to remain quite isolated from the busy world. As hosts, we are right next door for queries and information. Please read our reviews to see why people book.

28 Oct – 4 Nov

$1,456 AUD total

Guest favourite

Guesthouse in Cranham

4.99 out of 5 average rating, 153 reviews

The Organic Cotswolds Cowshed

Welcome to the The Organic Cotswolds Cowshed. Set in the heart of The Cotswolds, one of the most beautiful areas in the UK, we are offering the most organic and toxic free environment that we can for our guests (Covid regulations allowing!) which may be important to you if you are allergic or intolerant to such things as added fragrance to laundry soap or the chemicals used in regular cleaning chemicals and sprays. We also try to be as environmentally minded as possible.

20 – 27 Nov

$1,391 AUD total

Guest favourite

Guesthouse in Gloucester

4.96 out of 5 average rating, 339 reviews

The Hut and Tub

Cosy Centrally Heated Shepherds Hut With luxury hot tub In Quiet Rural Area The perfect 'country getaway' for two people. This small shepherds hut is tucked away in the heart of a quiet Gloucestershire village situated in the corner of our garden but completely private and not overlooked with its own decking and luxury hot tub overlooking fields and farmland. The river Severn is less than a mile away which has a footpath all the way to Tewkesbury and nearby pubs.

31 Dec – 7 Jan

$1,684 AUD total

Guest favourite

Guesthouse in Standish

4.98 out of 5 average rating, 490 reviews

Luxury Shepherd's Hut in The Cotswolds

Sans Souci is a bespoke Shepherd's hut, lovingly hand built to an incredibly high spec. Completed in April 2021, it has a double bed, and double sofa bed. There is a well-equipped kitchen, a shower room with sink and compost toilet, and a log burning stove. There are far reaching views of the Cotswold hills, which can be taken in from the South-facing deck. Enjoy al fresco meals, cooking over the fire pit in the garden or walks galore in the local countryside.

28 Sept – 5 Oct

$1,393 AUD total

Guest favourite

Guesthouse in Withington

4.99 out of 5 average rating, 257 reviews

Stylish studio apartment with breakfast hamper.

Nestled in the Cotswold countryside, Pillars Loft offers a hideaway perfect for two, with stylish interiors, modern amenities and luxurious home comforts. Bordering the regency spa town of Cheltenham and the charming market town of Cirencester, Pillars is perfectly located for those looking to enjoy a spot of retail therapy, fine dining or festival scene that Cheltenham is renowned for while also catering for those looking for a peaceful rural retreat.

24 – 31 Mar

$1,394 AUD total

Guest favourite

Guesthouse in Cheltenham

4.97 out of 5 average rating, 234 reviews

Private Annexe - double bedroom with en-suite

A detached annexe in Cheltenham with double bedroom and en-suite bathroom, this newly refurbished self-contained property has a private entrance via side gate and free on road parking. There are tea and coffee making facilities, mini fridge, flat screen smart TV and free Wi-Fi. 5 mins walk from Cheltenham train station - on race days there is a free shuttle from the station to the racecourse. Prices vary depending on time of year.

2 – 9 Sept

$965 AUD total

Guest favourite

Guesthouse in Cheltenham

4.98 out of 5 average rating, 115 reviews

Leighterton, a beautiful Cotswold hideaway

Leighterton is a new bolthole in the heart of the Cotswold. The small, but perfectly formed, annex offers a beautifully designed, well-equipped space to stay. Surrounded by fields guests can enjoy walks, cycling and exploring neighboring villages. We are also perfectly located for guests of weddings at Cripps and Stone Barn. Located in a separate building next to the main house you have both security and privacy.

15 – 22 May

$1,340 AUD total

Guest favourite

Guesthouse in Worcestershire

4.95 out of 5 average rating, 183 reviews

Cleeve Cottage (The Studio)

A small detached studio/annex, in the picturesque village of Bushley, ideal location for anyone looking to have a short break in the countryside just 1.5 miles from the old market town of Tewkesbury and only 20 minutes from Cheltenham so perfect for a weekend at the races. Plenty of stunning rural locations to be explored nearby, with easy access to the beautiful Malvern hills, fantastic for cycling and hiking

20 – 27 Oct

$1,119 AUD total

Guest favourite

Guesthouse in Cheltenham

4.96 out of 5 average rating, 153 reviews

Mulberry is our self contained small town house

Located a short walk from the centre of Cheltenham, this small town house has its own entrance, a ground floor living space with discreetly concealed kitchen and a first floor double bedroom with an en suite luxury shower room. We have enhanced our cleaning routine and thoroughly disinfect all the property between visitors. We closely follow the AIRBNB and GOVERNMENT guidelines for the safety of us all.

26 Aug – 2 Sept

$1,427 AUD total