Guesthouse vacation rentals in Cheltenham

Find and book unique guesthouse rentals on Airbnb

Top-rated guesthouse rentals in Cheltenham

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

0 of 0 items showing

1 of 3 pages

Top guest favorite

The open living area features a cozy seating arrangement with a large white couch adorned with patterned cushions. Green beams are visible on the ceiling. Natural light floods in through multiple windows, illuminating a dining space with a wooden table surrounded by chairs.

Guesthouse in Gloucestershire

4.99 out of 5 average rating, 146 reviews

Luxury self-catering for two in the Cotswolds

Situated on a farm between the picturesque villages of Broadway and Winchcombe this private annex is the ideal getaway or escape for visiting the Cotswolds. Spread over two floors the open ground floor contains a small fully equipped kitchen and comfortable seating area with large wood burner. There is a private outdoor area for your enjoyment. Upstairs has a super king size bed and ensuite bathroom. All bedlinen is 100% cotton with down duvet, pillows soft towels and lots of wardrobe space.

Top guest favorite

A spacious living room is illuminated by natural light from large glass doors that open to the garden. Comfortable sofas are arranged around a round coffee table, and a bookshelf is visible against the wall. Decorative curtains provide a pop of color.

Guesthouse in Twigworth

4.94 out of 5 average rating, 127 reviews

The Annex at Stonehaven

The Annex offers privacy, peace and serenity in a dog friendly rural location with plenty of relaxing outdoor space. The Annex has a bedroom with en-suite shower, a large kitchen, and living room with two sofa beds. There is parking, a courtyard and a fenced orchard at the back. We are between Cheltenham, Gloucester and Tewkesbury so perfect for exploring any of these towns. Mon-Fri your host grooms dogs in a room connected to the Annex. Dogs or driers might be heard during the day on weekdays.

Top guest favorite

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.

Guesthouse in Eckington

5 out of 5 average rating, 236 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

Guest favorite

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.

Guesthouse in Leigh

4.91 out of 5 average rating, 227 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.

Guest favorite

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.

Guesthouse in Cranham

4.97 out of 5 average rating, 207 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

Guest favorite

An inviting sleeping area is framed by whitewashed walls and wooden beams, featuring a spacious bed dressed in crisp white linens and topped with a soft grey throw. Bedside tables with warm, metallic lamps flank the bed, while an antique chest of drawers adds character to the space.

Guesthouse in Winchcombe

4.95 out of 5 average rating, 349 reviews

Charming ‘mini cottage’ bedroom and shower room

A pretty and private little Cotswold stone bakehouse converted to a bedroom and shower room with beautiful Cotswold views set in rolling farmland on edge of historic hamlet of Hailes. We are right on the Cotswold Way and an ideal stop off after the first leg or walk the myriad of footpaths around us straight from the door. Within easy access of Cheltenham racecourse and the lovely villages of the Cotswolds, the many country pubs or a visit to the amazing Giffords Circus.

Top guest favorite

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.

Guesthouse in Withington

5 out of 5 average rating, 434 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 favorite

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.

Guesthouse in Gloucestershire

4.91 out of 5 average rating, 346 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 favorite

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.

Guesthouse in Cheltenham

4.98 out of 5 average rating, 381 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 favorite

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.

Guesthouse in Cheltenham

4.97 out of 5 average rating, 172 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 favorite

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.

Guesthouse in Gloucestershire

4.92 out of 5 average rating, 581 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.

Top guest favorite

A well-lit two-story living area is shown, featuring a wooden staircase leading to a lofted bedroom. Large skylights above provide natural light. A built-in bookshelf and a television are visible on the lower level, alongside comfortable seating arranged for relaxation.

Guesthouse in Cleeve Hill

5 out of 5 average rating, 103 reviews

Chapel End

Set on Cleeve Hill, this converted chapel is a unique and peaceful getaway. Located on the Cotswold Way, it is ideal for walkers, is dog friendly and has fabulous views. Next door is the Rising Sun pub and it is a short walk to Cleeve Hill Golf Club. It is also perfect for horse-racing enthusiasts with the Cheltenham Racecourse close by.