
Guesthouse vacation rentals in Cheltenham
Find and book unique guesthouse rentals on Airbnb
Quick stats about guesthouse rentals in Cheltenham

Total vacation rentals
Explore 30 vacation rentals in Cheltenham

Nightly prices starting at
Cheltenham vacation rentals start at ﺩ.ﺇ 331 per night before taxes and fees

Verified guest reviews
Over 3,540 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wi-Fi availability
30 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
Top-rated guesthouse rentals in Cheltenham
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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.
4.96 out of 5 average rating, 271 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
4.84 out of 5 average rating, 164 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
4.96 out of 5 average rating, 246 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.
4.94 out of 5 average rating, 113 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.
5.0 out of 5 average rating, 542 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.
4.92 out of 5 average rating, 420 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).
4.96 out of 5 average rating, 140 reviews
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.
4.9 out of 5 average rating, 361 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.
4.87 out of 5 average rating, 136 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.
4.97 out of 5 average rating, 187 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!
4.88 out of 5 average rating, 582 reviews
Luxury Cotswold Lodge |Stunning View of Cheltenham
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.
4.91 out of 5 average rating, 694 reviewsPopular amenities for Cheltenham guesthouse rentals
Family-friendly guest house rentals

Luxury Shepherd's Hut in The Cotswolds
4.98 out of 5 average rating, 826 reviews
Cleeve Cottage (The Studio)
4.96 out of 5 average rating, 281 reviews
Luxury self-catering for two in the Cotswolds
4.99 out of 5 average rating, 170 reviews
Bright, airy Annex in village with stunning views
4.92 out of 5 average rating, 451 reviews
The Garden Studio Graywalls Stroud
4.86 out of 5 average rating, 713 reviews
Charming, detached, converted stable in Evesham.
4.97 out of 5 average rating, 210 reviews
Larks Nest - your gateway to the Cotswolds
4.98 out of 5 average rating, 314 reviews
Pippa’s Cottage-walk to Cirencester and Gastro Pub
4.97 out of 5 average rating, 515 reviewsGuest house rentals with a patio

Renovated cottage with views of Bredon Hill
4.99 out of 5 average rating, 313 reviews
Adorable One Bedroom Cotswold Studio
4.98 out of 5 average rating, 277 reviews
Charming guest house in stunning wooded valley
4.9 out of 5 average rating, 266 reviews
The Annex between the Cotswold Hills
4.87 out of 5 average rating, 274 reviews
Self contained annex with own entrance & parking.
4.97 out of 5 average rating, 526 reviews
Little Rosewood is a Cosy Cotswold Retreat
4.95 out of 5 average rating, 229 reviews
Dog Friendly Cosy cottage in the Cotswolds
4.99 out of 5 average rating, 144 reviews
Heron's Nest - Detached annexe in wooded valley
4.9 out of 5 average rating, 208 reviewsGuest house rentals with a washer and dryer

The Little House
4.99 out of 5 average rating, 108 reviews
Cotswold guest Annex & tennis court in 5* grounds
5.0 out of 5 average rating, 120 reviews
The Annex at Stonehaven
4.94 out of 5 average rating, 200 reviews
Cosy Cotswold Lodge with Hot Tub & Private Garden
4.97 out of 5 average rating, 307 reviews
Redmarley D'Abitot country lovers' retreat
4.95 out of 5 average rating, 163 reviews
Little gem at foot of Malvern Hills
4.95 out of 5 average rating, 239 reviews
Anthracite Annexe
4.97 out of 5 average rating, 154 reviews
Greencourt Loft, Cotswold Way, Middleyard, Stroud
4.95 out of 5 average rating, 363 reviewsWhen is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 485 | ﺩ.ﺇ 470 | ﺩ.ﺇ 617 | ﺩ.ﺇ 499 | ﺩ.ﺇ 547 | ﺩ.ﺇ 514 | ﺩ.ﺇ 433 | ﺩ.ﺇ 470 | ﺩ.ﺇ 433 | ﺩ.ﺇ 430 | ﺩ.ﺇ 422 | ﺩ.ﺇ 422 |
| Avg. temp | 5°C | 5°C | 7°C | 9°C | 12°C | 15°C | 18°C | 17°C | 15°C | 11°C | 7°C | 5°C |
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