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

Total holiday rentals
Explore 30 holiday rentals in Cheltenham

Nightly prices starting at
Cheltenham holiday rentals start at $126 AUD per night before taxes and fees

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

Pet-friendly accommodation
Find 10 rentals that welcome pets

Wi-Fi availability
30 of Cheltenham holiday 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 Guesthouses in Cheltenham
Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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
FamilyValueNearby

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.
ValueLocationCondition

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
LocationValueCheckout

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.
ValueLocationIndoor spaces

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.
ValueFamilyNearby

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.
LocationValueWalkability

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.
FamilyValueCondition

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).
LocationFamilyAmenities

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.
LocationFamilyDecor

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.
FamilyLocationLayout

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!
FamilyValueParks

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.
FamilyValueBarbecue
Popular amenities for Cheltenham guesthouses
Family-Friendly guesthouses

Luxury Shepherd's Hut in The Cotswolds
FamilyValueLayout

The Organic Cotswolds Cowshed
FamilyValueComfort

Cleeve Cottage (The Studio)
ValueLocationView

Luxury self-catering for two in the Cotswolds
LocationFamilyHiking

Artist's studio in Edge in stunning countryside.
ValueLocationSleep quality

The Annex at The Oaks
LocationFamilyLaundry

The Cider Press with Games Room
LocationValueCheck-in

Bright, airy Annex in village with stunning views
ValueLocationView
Guesthouses with a patio

Charming guest house in stunning wooded valley
FamilyValueLong stay

Adorable One Bedroom Cotswold Studio
LocationFamilyAccess

Little Rosewood is a Cosy Cotswold Retreat
LocationFamilyComfort

Nuthatch Chalet
FamilyLocationAccuracy

Self contained annex with own entrance & parking.
LocationValueComfort

The Hide; a Unique Annex with rural views
LocationValueBreakfast

The Annex between the Cotswold Hills
ValueFamilySleep quality

Small Cotswold cottage / annex
FamilyValueCheckout
Guest house rentals with a washing machine and dryer

The Little House
LocationValueNearby

Cotswold retreat: a stylish stay at Little Orchard
FamilyLocationKitchen

Cosy Cotswold Lodge with Hot Tub & Private Garden
ValueFamilyBarbecue

Redmarley D'Abitot country lovers' retreat
FamilyLocationBackyard

Gardener's Pavilion | Malvern
FamilyLocationLayout

Cotswold guest Annex & tennis court in 5* grounds
FamilyLocationBathroom

Little gem at foot of Malvern Hills
ValueFamilyWalkability

Self-contained property in Rodborough
FamilyLocationSleep quality
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $185 AUD | $180 AUD | $236 AUD | $191 AUD | $209 AUD | $197 AUD | $166 AUD | $180 AUD | $166 AUD | $164 AUD | $161 AUD | $161 AUD |
| 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
- Rentals with breakfast Cheltenham
- Serviced apartment rentals Cheltenham
- Bed and breakfasts Cheltenham
- Apartment rentals Cheltenham
- House rentals Cheltenham
- Private suite rentals Cheltenham
- Villa rentals Cheltenham
- Cottage rentals Cheltenham
- Townhouse rentals Cheltenham
- Rentals with a hot tub Cheltenham
- Condo rentals Cheltenham
- Rentals with lake access Cheltenham
- Pet-friendly rentals Cheltenham
- Cabin rentals Cheltenham
- Family-friendly rentals Cheltenham
- Guesthouse rentals Gloucestershire
- Guesthouse rentals England
- Guesthouse rentals United Kingdom
- Silverstone Circuit
- Cotswolds AONB
- Longleat Safari Park
- University of Oxford
- National Exhibition Centre
- Blenheim Palace
- Lower Mill Estate
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Highclere Castle
- Cheltenham Racecourse
- West Midland Safari Park
- University of Warwick
- Utilita Arena Birmingham
- Cadbury World
- Ludlow Castle
- Cotswold Wildlife Park
- Coventry Building Society Arena
- University of Birmingham
- Bath Abbey
- Puzzlewood
- Sudeley Castle
- Bicester Village
- Alexander Stadium
- Warwick Castle




