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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 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.
Guest house in Gloucestershire
4.99 out of 5 average rating, 158 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 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
4.99 out of 5 average rating, 291 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
Guest house in Toddington
4.95 out of 5 average rating, 235 reviews

Cotswold retreat: a stylish stay at Little Orchard

Little Orchard sits on a quiet lane, in the charming Cotswold village of Toddington, Glos. This light and airy apartment has an open plan living, dining and kitchen area, a separate king-sized bedroom with en-suite shower room. Situated above the garage to the side of the main property, with ample parking, the apartment has pleasant views and is only a few minutes walk from the ancient village church with many country walks from the door. You can enjoy the evening sun on the private patio.

Top guest favourite
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.
Guest house in Twigworth
4.95 out of 5 average rating, 168 reviews

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 shower room, 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.

Top guest favourite
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.
Guest house in Standish
4.98 out of 5 average rating, 795 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.

Guest favourite
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.
Guest house in Cheltenham
4.93 out of 5 average rating, 109 reviews

Prestbury Village Annex.

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.

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 Cheltenham
4.97 out of 5 average rating, 180 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.

Top guest favourite
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.
Guest house in Cheltenham
4.88 out of 5 average rating, 555 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 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, 657 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 favourite
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.
Guest house in Bourton-on-the-Water
4.98 out of 5 average rating, 296 reviews

Larks Nest - your gateway to the Cotswolds

Larks Nest is situated at the edge of the famous village Bourton-on-the-Water one of the most popular and beautiful villages in the Cotswolds with a good selection of shops, restaurants and pubs. The location is the ideal base to explore the Cotswolds with its many attractions.

Top guest favourite
A charming cottage exterior is displayed, featuring traditional Cotswold stone walls and wooden-framed windows. Lush greenery surrounds the entrance, with a variety of potted plants and flowers lining the pathway. A cobblestone path leads to a light green door, inviting guests into a tranquil setting.
Guest house in Charlton Kings
4.94 out of 5 average rating, 347 reviews

Beautiful Cotswold Cottage

Situated in the heart of the Cotswolds and being officially recognised as an Area of Natural Outstanding Beauty, this self-contained cottage offers wonderful countryside scenery whilst being only a 10 minute drive from Cheltenham town centre.

Top guest favourite
A welcoming entrance is framed by lush green vines and a blooming purple flower. A wooden door with a grid-patterned window provides access to The Little Grey House, with natural stone tiles contributing to the serene ambiance.
Guest house in Gloucestershire
4.99 out of 5 average rating, 174 reviews

Cheltenham's Little Grey House

The Little Grey House is a stylish hidden retreat for those wanting to visit Cheltenham, explore the Cotswolds many beautiful walks and villages or simply for a base during Cheltenham’s infamous Festivals and Racing Events.

Popular amenities for guest house rentals in Cheltenham

When is the best time to visit Cheltenham?

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Avg. price$169 SGD$163 SGD$215 SGD$147 SGD$153 SGD$147 SGD$151 SGD$163 SGD$151 SGD$149 SGD$147 SGD$147 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 $89 SGD per night before taxes and fees

  • Verified guest reviews

    Over 3,400 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