Guesthouse vacation rentals in Cheltenham

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Top-rated guesthouse rentals in Cheltenham

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

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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 in Gloucestershire
4.99 out of 5 average rating, 151 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
Guesthouse in Stroud
4.97 out of 5 average rating, 102 reviews

Amberley Coach House, nr Stroud

Cosy self-contained room with comfy kingsize bed, double sofabed and en-suite shower on the upper floor of a separate building across the garden from the house. Beautiful Cotswolds village setting high on a hill between the towns of Nailsworth (2 miles) and Stroud (3 miles). Wifi. No kitchen facilities but there's a kettle and big coolbox. Moments from gorgeous National Trust common land. Three pubs, a hotel and a shop/café in the church within 5-20 minutes' walk. Step-free access via garden.

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, 239 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
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.
Guesthouse in Minchinhampton
4.99 out of 5 average rating, 367 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 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, 212 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 in Westwell
4.99 out of 5 average rating, 245 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 in Withington
5 out of 5 average rating, 451 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 Henleaze
4.91 out of 5 average rating, 358 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 in Henleaze
4.96 out of 5 average rating, 102 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 in Worcestershire
4.95 out of 5 average rating, 243 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 in Henleaze
4.97 out of 5 average rating, 176 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, 591 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 Cheltenham guesthouse rentals

When is the best time to visit Cheltenham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$23,206 GYDG$22,370 GYDG$30,732 GYDG$24,042 GYDG$25,087 GYDG$24,042 GYDG$22,579 GYDG$23,206 GYDG$23,415 GYDG$25,924 GYDG$26,133 GYDG$22,579 GYD
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Quick stats about guesthouse rentals in Cheltenham

  • Total vacation rentals

    Explore 20 vacation rentals in Cheltenham

  • Nightly prices starting at

    Cheltenham vacation rentals start at G$12,544 GYD 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

  • Wi-Fi availability

    20 of Cheltenham vacation rentals include wi-fi 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