Guesthouse vacation rentals in Cheltenham

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Top-rated guesthouse rentals in Cheltenham

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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

4.99 out of 5 average rating, 149 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

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

5 out of 5 average rating, 243 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

4.91 out of 5 average rating, 233 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 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

4.97 out of 5 average rating, 210 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 favorite

A stone annex is shown, framed by a well-kept lawn and gravel pathway. The entrance features a wooden porch, leading to an open doorway. Lush greenery surrounds the property, with a white gate in the background, contributing to a serene outdoor environment.

Guesthouse

4.99 out of 5 average rating, 240 reviews

Small Cotswold cottage / annex

Self-contained single-storey annex set in its own grounds. Newly decorated with off-road parking; south-facing garden with terrace. Ideal base for exploring the Cotswolds and minutes away from Burford and Jeremy Clarkson's pub, the Farmer’s Dog. Perfectly positioned to visit Bourton-on-the-Water, Stow-on-the-Wold and Bibury. 6 miles from RAF Brize Norton. Using non-toxic household products where possible and putting sustainability at the forefront by using refillable bottles.

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

5 out of 5 average rating, 447 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

4.91 out of 5 average rating, 352 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 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.

Guesthouse

4.96 out of 5 average rating, 100 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 favorite

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.

Guesthouse

4.95 out of 5 average rating, 242 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 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

4.97 out of 5 average rating, 174 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

A quaint entrance reveals a wooden door with decorative glass, leading to a private courtyard. Two folding chairs are positioned at a small table beside a window, surrounded by charming stone paving and lush greenery in the background.

Guesthouse

4.88 out of 5 average rating, 521 reviews

Self-contained unit, parking & 3 mins walk to town

Period apartment with own private access, feature fireplace with wood-burning stove and black beams in ceiling. Modern kitchen and ensuite wet room. Fully equipped with all necessary kitchen equipment and toiletries. Use of private courtyard garden with table and chairs. Off street parking on drive. At end of quiet cul-de-sac next to beautiful park. Very peaceful with no traffic noise. Very comfy bed!

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

4.92 out of 5 average rating, 588 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.