Guesthouse vacation rentals in Cheltenham

5.0 out of 5 average rating, 109 reviews

A welcoming living area is furnished with two beige sofas and a cozy ottoman. A wooden coffee table sits centrally on a light carpet. Natural light filters through the window, complemented by soft curtains, enhancing the calm ambiance.

Guesthouse

The Jays countryside annexe

A village in the heart of the Cotswolds, great for walkers, close to Bibury, Broadway, Stow on the Wold. Burford's Cotwold Wildlife Park & Guiting Power's 'Farm Park', both near. Cirencester, 3 miles away, is an historic market town boasting several large supermarkets, Leisure Centre, ample Pubs and Restaurants. Outdoor pursuits at Cotswold Water Park, Golf Courses, Badminton Trials. 7 miles from Fairford, ideally placed for the International Air Tattoo. Culture in Regency Cheltenham.

4.98 out of 5 average rating, 559 reviews

The exterior of a unique stone dovecote is displayed, featuring a rounded structure topped with a conical roof. A single door is visible at the base, framed by flowers and greenery. Sunlight casts soft shadows on the textured stone walls, enhancing its rustic charm.

Guesthouse in Bibury

Bibury Hidden Dovecote (Grade II Listed)

We are delighted to reopen the dovecote after some essential improvements. We can now offer availability from this spring. A completely unique experience. This converted dovecote has a stunning bathroom, copper bath, wet room shower and beautiful double bedroom with terrace. Situated in a quiet but central location in Bibury with parking and breakfast. Perfect for a secret romantic break. Situated conveniently for Burford, Cirencester and Cheltenham, you can explore South Cotswolds.

An open studio space is showcased, featuring a double bed with two decorative pillows. A kitchenette is visible with essential appliances. A smart TV is mounted on the wall, and a small glass table with two chairs is positioned in the area. Natural light is entering through a sliding door.

4.83 out of 5 average rating, 159 reviews

Lovely self-contained annexe with private entrance

A lovely, fully furnished, self-contained, compact but perfectly formed annexe, perfect for 1 or 2 guests in a quiet Cheltenham suburb. Ideal for work related stay, visiting the Cotswolds, viewing properties etc. 15 min walk to/from train station and 1 min from main bus route. 30 minute walk to Montpellier / centre of town. Features a king bed, en-suite bathroom, fully equipped kitchenette, smart 32" TV, broadband internet, and workspace. Unrestricted parking on the drive or on-street

4.94 out of 5 average rating, 195 reviews

The exterior of The Annex is presented, featuring a fenced courtyard adorned with string lights that create a gentle glow. The entrance showcases large glass doors leading into the interior, framed by lush greenery in the background.

Guesthouse in Twigworth

The Annex at Stonehaven

The Annex offers dog friendly accommodation with plenty of outdoor space. It has a bedroom with en-suite shower, a large kitchen and open plan living room with double bed, dining and sofa areas. There is parking, a courtyard and garden. We are between Cheltenham, Gloucester and Tewkesbury. Mon-Fri your host grooms dogs in a room connected to the Annex. Dogs or driers might be heard during the day on weekdays and access needed to cleaning cupboard and tumble dryer in annex.

A bright living area features a comfortable couch adorned with decorative pillows, facing a television. Light from the patio doors illuminates the space, which includes a small table and chair set visible through the doors. Neutral tones are complemented by a textured rug on the floor.

4.94 out of 5 average rating, 108 reviews

Self contained annex adjoining a family home.

Come and enjoy a relaxing stay in our beautiful one bedroom self contained annex with separate living space, and off road parking, all of which is adjoining our family home. We are approx. 1.5 miles from the M5 and 10 minutes from Cheltenham town centre. Cheltenham boasts an array of shops and boutiques, coffee shops and bars, for you to enjoy during your stay. Cheltenham hosts many events such as racing, the science, literature and jazz festivals.

5.0 out of 5 average rating, 534 reviews

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

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.

Guesthouse in Gloucestershire

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.

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.

4.92 out of 5 average rating, 418 reviews

4.96 out of 5 average rating, 138 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).

4.9 out of 5 average rating, 360 reviews

A charming studio is enveloped by greenery, featuring a gravel courtyard with a stone planter at its center. The exterior showcases a red-tiled roof and wooden siding, while a small table and chairs are positioned nearby next to a barbecue, inviting outdoor relaxation.

Guesthouse in Painswick

Artist's studio in Edge in stunning countryside.

This is a well equipped studio in the Cotswolds. It's at the end of a singletrack no through road about 1/2 mile from the Cotswold way and at the junction of several footpaths. The nearest towns are Painswick,which is 1 mile away, and Stroud where there is a train station and supermarkets. The studio has a sleeping area with a king size double bed. It is separated by a bookcase from the main living area. where there is also a sofa.

Superhost

A pathway lined with lush greenery leads to a charming dwelling partially hidden by trees and bushes. The gravel drive is framed by manicured hedges, creating a serene entrance. Natural light filters through the foliage, highlighting the tranquil setting of the home.

4.87 out of 5 average rating, 133 reviews

Prestbury Village Annexe.

Nestled in the beautiful cotswold hills and minutes from Cheltenham town centre, this stunningly located Prestbury Village Annexe is 5 minutes walk to The Cheltenham Racecourse and 3 doors down from The Plough pub. Comfortable and cozy with all amenities, this double bed dwelling is perfect for those attending the numerous horse races, or for those that want a quiet, peaceful break. Opposite the 13th century church of St Mary.

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.

4.97 out of 5 average rating, 183 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.

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.

4.88 out of 5 average rating, 578 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!

Popular amenities for Cheltenham guesthouse rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Family-friendly guest house rentals

4.98 out of 5 average rating, 821 reviews

A charming wooden shepherd's hut is set on a spacious deck, surrounded by lush greenery. Flower beds in vibrant colors enhance the outdoor space, while a fire pit, constructed with stone, invites cozy gatherings. A wood-burning stove is visible near the entrance.

Guesthouse in Standish

Luxury Shepherd's Hut in The Cotswolds

Guesthouse in Worcestershire

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.

Cleeve Cottage (The Studio)

4.96 out of 5 average rating, 280 reviews

4.96 out of 5 average rating, 243 reviews

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

The Organic Cotswolds Cowshed

4.99 out of 5 average rating, 168 reviews

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 Stanton

Luxury self-catering for two in the Cotswolds

4.92 out of 5 average rating, 445 reviews

Guesthouse in Randwick

Bright, airy Annex in village with stunning views

Superhost

A modern wooden studio is enveloped by lush greenery and a low wooden fence. A shaded seating area is visible, alongside vibrant plants climbing the structure. The surrounding natural landscape enhances the sense of privacy and tranquility.

Guesthouse in Gloucestershire

The Garden Studio Graywalls Stroud

4.86 out of 5 average rating, 709 reviews

Guesthouse in Bourton-on-the-Water

An open-plan studio features a spacious bed with light bedding, flanked by stylish lamps. A modern kitchen with sleek cabinetry and appliances is visible, complemented by a breakfast bar. Warm wood beams accentuate the ceiling, adding charm to the cozy atmosphere.

Larks Nest - your gateway to the Cotswolds

4.98 out of 5 average rating, 313 reviews

Guesthouse in Cirencester

A private roof terrace is shown, featuring green outdoor furniture, including two chairs with cushions and a small table. Surrounding foliage adds a vibrant touch, while wooden decking creates a warm, inviting space for relaxation.

Pippa’s Cottage-walk to Cirencester and Gastro Pub

4.97 out of 5 average rating, 512 reviews

Guest house rentals with a patio

4.99 out of 5 average rating, 308 reviews

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

Renovated cottage with views of Bredon Hill

4.9 out of 5 average rating, 263 reviews

A wooden guest house is nestled among lush greenery, with large glass windows reflecting warm light. The surrounding countryside extends into rolling hills, hinting at scenic walking trails. Soft autumn hues from nearby trees add a touch of seasonal charm to the tranquil atmosphere.

Guesthouse in Horsley

Charming guest house in stunning wooded valley

4.98 out of 5 average rating, 276 reviews

A two-story building features a large glass front entrance, providing an inviting view of the interior. A small outdoor seating area with a table and chairs is visible, surrounded by neatly landscaped gardens and natural stone walls.

Guesthouse in Nailsworth

Adorable One Bedroom Cotswold Studio

Superhost

The exterior features a newly renovated entrance with a dark wooden door framed by large glass panels. Decorative planters filled with lush greenery sit on either side of the door, with a sunny blue sky overhead.

Guesthouse in Sedgeberrow

The Annex between the Cotswold Hills

4.87 out of 5 average rating, 266 reviews

Guesthouse in Stow-on-the-Wold

A double bed is featured with decorative pillows and a cozy gray throw. Light fills the room through a nearby window. Steps lead to a welcoming dining area visible in the background, enhancing the sense of space and connection within the cottage.

Little Rosewood is a Cosy Cotswold Retreat

4.95 out of 5 average rating, 227 reviews

Guesthouse in Chipping Campden

The Lodge, A Cosy Cotswold Retreat

4.88 out of 5 average rating, 112 reviews

4.9 out of 5 average rating, 205 reviews

The kitchenette features wooden cabinetry, a sink, and modern appliances, including a microwave and induction hob. Shelves hold dishes and utensils. A potted plant and wooden dining area are visible, creating an airy and clean environment. Stairs lead to the upper level.

Guesthouse in Nailsworth

Heron's Nest - Detached annexe in wooded valley

Guesthouse in Cleeve Prior

The cottage is seen from the front, featuring a characteristic brick façade and a pink door. A paved patio area is visible, surrounded by greenery and garden furniture. Large windows reflect natural light, indicating a bright and inviting atmosphere.

Dog Friendly Cosy cottage in the Cotswolds

4.99 out of 5 average rating, 142 reviews

Guest house rentals with a washer and dryer

4.95 out of 5 average rating, 264 reviews

Guesthouse in Toddington

Cotswold retreat: a stylish stay at Little Orchard

4.99 out of 5 average rating, 105 reviews

A cozy living area features a stylish log burner with a warm flame, complemented by a glass coffee table displaying stacked books. Light curtains gently drape over large windows, allowing natural light to fill the space, while a comfortable couch adorned with a checked throw invites relaxation.

Guesthouse in Naunton

The Little House

Guesthouse in Cirencester

A well-lit bedroom features a spacious bed draped in a white comforter, complemented by a vibrant blue and red throw. A small chair adds charm, and natural light filters through the window, illuminating the serene space.

Cotswold guest Annex & tennis court in 5* grounds

5.0 out of 5 average rating, 116 reviews

Guesthouse in Gloucestershire

A wide view of rolling green hills stretches across the landscape, framed by large trees and patches of wildflowers. A wooden fence defines the foreground, offering a connection to the peaceful surroundings under a partly cloudy sky.

Self-contained property in Rodborough

4.93 out of 5 average rating, 126 reviews

Guesthouse in Redmarley D'Abitot

Redmarley D'Abitot country lovers' retreat

4.95 out of 5 average rating, 161 reviews

Guesthouse in Great Malvern

A modern single-storey guest house is set against a backdrop of lush greenery. Smooth glass panels provide a view of an outdoor terrace, adorned with a café-style table and chairs. Vibrant flower beds, featuring purple, pink, and white blooms, frame the inviting structure.

Gardener's Pavilion | Malvern

4.99 out of 5 average rating, 157 reviews

4.97 out of 5 average rating, 307 reviews

The exterior of April Cottage Lodge features a charming stone façade, with a welcoming entrance door framed by a small porch. A lush green lawn surrounds the house, complemented by a potted plant and outdoor furniture nearby, creating an inviting outdoor space.

Guesthouse in Toddington

Cosy Cotswold Lodge with Hot Tub & Private Garden