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

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.

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.

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

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.

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.

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).

Private Annexe - double bedroom with en-suite
A detached annexe in Cheltenham with double bedroom and en-suite bathroom, this is a self-contained property has a private entrance via side gate and free on road parking. There are tea and coffee making facilities, mini fridge, flat screen smart TV and free Wi-Fi. 5 mins walk from Cheltenham train station - on race days there is a free shuttle from the station to the racecourse. Prices vary depending on time of year.

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.

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!

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.

Chapel End
Set on Cleeve Hill, this converted chapel is a unique and peaceful getaway. Located on the Cotswold Way, it is ideal for walkers, is dog friendly and has fabulous views. Next door is the Rising Sun pub and it is a short walk to Cleeve Hill Golf Club. It is also perfect for horse-racing enthusiasts with the Cheltenham Racecourse close by.
Popular amenities for Cheltenham guesthouses
Family-Friendly guesthouses

Private Studio- Cirencester

Entire guesthouse set within Cotswold Water Park

The Small House with a Big Welcome

The Cider Press with Games Room

B&B in Beautiful Cotswold Annex

Charming, detached, converted stable in Evesham.

A Cosy Cotswold Woodland Cabin

Detached Annex in idyllic Countryside
Guesthouses with a patio

Little Rosewood is a Cosy Cotswold Retreat

Prestbury Village Annexe.

Adorable One Bedroom Cotswold Studio

Small Cotswold cottage / annex

Gorgeous 1 Bed Cotswold rural studio. With Parking

Stunning rural retreat perfect for couples & dogs

Charming guest house in stunning wooded valley

The School House, Cambridge, Gloucestershire
Guest house rentals with a washing machine and dryer

Golden Stone Country Retreat, Cotswolds

Gardener's Pavilion | Malvern

Cosy Cotswold Lodge with Private Garden & Hot Tub

Self-contained property in Rodborough

Anthracite Annex

Guest house close to station

Little gem at foot of Malvern Hills

Greencourt Loft, Cotswold Way, Middleyard, Stroud
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $196 NZD | $189 NZD | $260 NZD | $204 NZD | $212 NZD | $204 NZD | $209 NZD | $227 NZD | $209 NZD | $219 NZD | $221 NZD | $191 NZD |
| 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 |
Quick stats about guesthouse rentals in Cheltenham

Total holiday rentals
Explore 20 holiday rentals in Cheltenham

Nightly prices starting at
Cheltenham holiday rentals start at $106 NZD 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 holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
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