
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.

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.
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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.
ValueFamilyBreakfast

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.
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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
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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.
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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.
FamilyValueLong stay

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.
ValueFamilyOutdoor spaces

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.
ValueFamilyTV

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).
LocationFamilyParking

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.
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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.
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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!
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Popular amenities for Cheltenham guesthouse rentals
Family-friendly guest house rentals

Cleeve Cottage (The Studio)
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Luxury Shepherd's Hut in The Cotswolds
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The Organic Cotswolds Cowshed
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Artist's studio in Edge in stunning countryside.
LocationFamilyNearby

The Garden Studio Graywalls Stroud
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Bright, airy Annex in village with stunning views
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Larks Nest - your gateway to the Cotswolds
FamilyLocationView

Charming, detached, converted stable in Evesham.
FamilyLocationNearby
Guest house rentals with a patio

Renovated cottage with views of Bredon Hill
LocationFamilyHiking

Charming guest house in stunning wooded valley
FamilyLocationWalkability

Adorable One Bedroom Cotswold Studio
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The Annex between the Cotswold Hills
FamilyLocationGetting around

Little Rosewood is a Cosy Cotswold Retreat
FamilyValueAccuracy

The Lodge, A Cosy Cotswold Retreat
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Self contained annex with own entrance & parking.
ValueLocationSleep quality

Dog Friendly Cosy cottage in the Cotswolds
ValueFamilyCondition
Guest house rentals with a washer and dryer

The Little House
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Self-contained property in Rodborough
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Cotswold guest Annex & tennis court in 5* grounds
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Greencourt Loft, Cotswold Way, Middleyard, Stroud
ValueFamilyTV

Gardener's Pavilion | Malvern
LocationFamilyGrill

Cosy Cotswold Lodge with Hot Tub & Private Garden
FamilyValueBackyard

Redmarley D'Abitot country lovers' retreat
LocationFamilyLaundry

Little gem at foot of Malvern Hills
ValueLocationWifi
When 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 |
Destinations to explore
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- Silverstone Circuit
- Cotswolds AONB
- Longleat Safari Park
- University of Oxford
- Blenheim Palace
- National Exhibition Centre
- Lower Mill Estate
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Highclere Castle
- West Midland Safari Park
- Cheltenham Racecourse
- Utilita Arena Birmingham
- Cadbury World
- Ludlow Castle
- Cotswold Wildlife Park
- Coventry Building Society Arena
- University of Birmingham
- Bath Abbey
- Puzzlewood
- Sudeley Castle
- Bicester Village
- University of Warwick
- Alexander Stadium
- No. 1 Royal Crescent




