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Guest house holiday rentals in Cheltenham

Find and book unique guest house rentals on Airbnb

Top-rated guest house rentals in Cheltenham

Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of Cedar Cottage features a charming red brick facade with a distinctive glazed oak door and a Juliet balcony above. Large glass doors invite natural light into the open-plan interior. A gravel path leads to a secure perimeter, enhancing the cottage's welcoming appeal.
Guest house in Eckington
5 out of 5 average rating, 250 reviews

Renovated cottage with views of Bredon Hill

Cedar Cottage is a recently renovated self contained cottage adjacent to our home with its own entrance and secure parking on site. It has everything you need to make your stay comfortable with high quality stylish furnishings including a king sized bed with Emma mattress. The village has 2 pubs and a village shop and is perfectly situated for easy access to Cheltenham Festivals, Upton-upon-Severn and the Cotswolds. Wonderful walks directly from the cottage. Bike storage & EV Charger available

Top guest favourite
A charming brick exterior showcases the annexe, surrounded by well-maintained greenery. The sloped roof and wooden door complement the rustic feel. Flowering plants in colorful pots are positioned near the entrance, and a gravel path leads to the entrance, inviting relaxation in a serene setting.
Guest house in Leigh
4.91 out of 5 average rating, 245 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.

Top guest favourite
A light-filled living area features a comfortable gray sofa and a wall-mounted television. Glass doors open to a private garden with a grassy area and outdoor seating, creating a seamless connection between indoor and outdoor spaces.
Guest house in Redmarley D'Abitot
4.96 out of 5 average rating, 134 reviews

Redmarley D'Abitot country lovers' retreat

This recently refurbished, ground level, self contained unit, is set in a rural location. The unit consists of a fully fitted, well equipped kitchen and living area, shower room and bedroom with a king size bed. Guests have their own designated parking space. Private entrance with keylock. The property also has a private, fully enclosed garden. Ideal for walkers or those just seeking a quiet getaway. Close to the market town of Ledbury. Ideal base for visiting the Malverns or Cotswolds.

Top guest favourite
The cottage exterior is surrounded by vibrant flowers and lush greenery. A gravel pathway leads to the inviting entrance, with colorful plants in pots enhancing the garden's charm. Natural stone walls reflect the Cotswold style under a clear, bright sky.
Guest house in Minchinhampton
4.99 out of 5 average rating, 374 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.

Top guest favourite
An outdoor garden area is featured, showcasing a stone patio with a large dining table surrounded by chairs. Potted plants and lush greenery create a natural setting, while the rustic wooden structures of the property provide a charming backdrop.
Guest house in Cranham
4.97 out of 5 average rating, 215 reviews

The Organic Cotswolds Cowshed

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 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 non-bio cleaning chemicals and sprays. I also have a shepherds hut on the property that sleeps two. See my other listing 1 DOG welcome. No other pets

Top guest favourite
A spacious bed dressed in luxurious linens is accented by two large pillows. Bedside tables with lamps provide soft lighting, while a patterned blind offers privacy. The wooden beams overhead add warmth to the stylish and inviting bedroom environment.
Guest house in Withington
5 out of 5 average rating, 459 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.

Top guest favourite
The exterior features a newly refurbished annexe with a clean, modern design. A stone pathway leads to a private entrance, surrounded by gravel and paving. A small area of artificial grass and a garden shed are visible, providing a welcoming outdoor space.
Guest house in Henleaze
4.92 out of 5 average rating, 366 reviews

Beautiful Self-Contained Annexe in Cheltenham

A lovely, newly refurbished annexe, perfect for 1 or 2 guests within good distance to the town center. A cosy, fully functioning, self-contained home from home featuring a double bed, kitchenette, en suite bathroom, 32" TV, heated floor and radiator with a private entrance. Located a 30 minute walk from the town centre and the Brewery Quarter, which is full of restaurants and bars, 2 cinemas, Mr Mulligans Adventure Golf and Hollywood Bowl.

Top guest favourite
A bright open-plan living area is showcased with large windows allowing natural light to fill the space. A modern dining table is set with plates, and two lounge chairs are positioned invitingly in the corner. Light wooden floors complement the minimalistic decor.
Guest house in Henleaze
4.95 out of 5 average rating, 109 reviews

Two Double Bedrooms Guest Annexe with EV Charging

A 2 Bedroom guest annexe within 100 yards of Cheltenham Race Course and within a 10 minute walk to the Town Centre. This property is tucked in the grounds of the main house and offers secure gated parking. The accommodation comprises open plan living space with fantastic views of Cleeve Hill and two double bedrooms. Use of laundry facilities and home gym if required (Subject to Availability). EV Charging available (separate charge).

Top guest favourite
A comfortable bedroom features a double bed with a patterned comforter and neatly arranged pillows. Natural light floods in through two windows with blinds. A small desk with a chair is positioned beside the bed, and a flat-screen TV is mounted on the wall.
Guest house in Henleaze
4.98 out of 5 average rating, 392 reviews

Private Annexe - double bedroom with en-suite

A detached annexe in Cheltenham with double bedroom and en-suite bathroom, this is a 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.

Top guest favourite
The exterior of a small wooden studio features a large window with a view of the surrounding countryside. A bench is positioned near a gravel path. The lawn is neatly maintained, leading to a wooden gate with a paddock visible in the background.
Guest house in Worcestershire
4.96 out of 5 average rating, 247 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

Top guest favourite
A cozy seating area features a neutral-colored sofa alongside a blue accent chair. A large mirror reflects light and adds depth to the space. A small side table holds a vase with yellow flowers, complemented by framed artwork on the wall.
Guest house in Henleaze
4.97 out of 5 average rating, 178 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.

Guest favourite
The lodge is viewed from a wooden gate, framed by trees. The structure features large glass windows, revealing a bright and open design. Rolling hills can be seen in the distance under a clear blue sky.
Guest house in Gloucestershire
4.92 out of 5 average rating, 602 reviews

Cotswold lodge with amazing views and famous walks

Enjoying spectacular views this 2 bedroom, dog friendly lodge sits on the top of Leckhampton Hill, enjoying easy access to the famous ‘Cotswold Way’ walk and is a 5 minute drive from the town centre of regency Cheltenham. The Lodge also includes a 3.5m outdoor kitchen looking over The Malvern Hills. The kitchen includes a large built in BBQ, a pizza oven and sink.

Popular amenities for guest house rentals in Cheltenham

When is the best time to visit Cheltenham?

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Avg. price$145 SGD$140 SGD$192 SGD$150 SGD$157 SGD$150 SGD$154 SGD$167 SGD$154 SGD$162 SGD$163 SGD$141 SGD
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Quick stats about guest house rentals in Cheltenham

  • Total holiday rentals

    Explore 20 holiday rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham holiday rentals start at $78 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,060 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Cheltenham holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Cheltenham rentals

  • 4.9 Average rating

    Cheltenham stays are highly rated by guests – averaging 4.9 out of 5!

  • Nearby attractions

    Cheltenham’s top spots include Cheltenham Racecourse, Pittville Park and Everyman Theatre

Destinations to explore