
Guest house holiday rentals in Cheltenham
Find and book unique guest house rentals on Airbnb
Quick stats about guest house rentals in Cheltenham

Total holiday rentals
Explore 20 holiday rentals in Cheltenham

Nightly prices starting at
Cheltenham holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 3,400 verified reviews to help you choose

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Cheltenham holiday rentals include wifi 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 guest house rentals in Cheltenham
Guests agree: these guest house 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.

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

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 shower room, 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.

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.

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).

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.

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!
Popular amenities for guest house rentals in Cheltenham
Family-friendly guest house rentals

Cub Cottage Nr Broadway Cotswolds Tennis Court

A Cotswold Cabin with Great Views and a Hot Tub

The Garden Studio Graywalls Stroud

Meadow Lodge quiet annexe in countryside

Charming, detached, quiet stable in Evesham town.

A Cosy Cotswold Woodland Cabin

The Annex at The Oaks

Ivy Studio
Guest house rentals with a patio

Little Rosewood is a Cosy Cotswold Retreat

Central Stow: Private Studio with Garden & Parking

Self contained annex with own entrance & parking.

Adorable One Bedroom Cotswold Studio

Nuthatch Chalet

Small Cotswold cottage / annex

The Hide; a Unique Annex with rural views

Charming guest house in stunning wooded valley
Guest house rentals with a washing machine and dryer

Golden Stone Country Retreat, Cotswolds

Immaculate riverside Cotswold cottage - sleeps 4-6

Scenic 2 Bed Lodge with hot tub and indoor pool

Gardener's Pavilion | Malvern

Cosy Cotswold Lodge with Hot Tub & Private Garden

Fox Barn, charming hide-away in Moreton-in-Marsh

Self-contained property in Rodborough

Anthracite Annex
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $170 SGD | $164 SGD | $216 SGD | $148 SGD | $154 SGD | $148 SGD | $152 SGD | $164 SGD | $152 SGD | $150 SGD | $148 SGD | $148 SGD |
| 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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- Rentals with a firepit Cheltenham
- Rentals with a patio Cheltenham
- Rentals with a hot tub Cheltenham
- Rentals with a fireplace Cheltenham
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- Guest house rentals Gloucestershire
- Guest house rentals England
- Guest house rentals United Kingdom
- Cotswolds AONB
- University of Oxford
- Blenheim Palace
- Utilita Arena Birmingham
- Lower Mill Estate
- Silverstone Circuit
- Highclere Castle
- Cheltenham Racecourse
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- West Midland Safari Park
- Cadbury World
- Bath Abbey
- University of Warwick
- Ludlow Castle
- Sudeley Castle
- Waddesdon Manor
- Puzzlewood
- No. 1 Royal Crescent
- National Exhibition Centre
- Coventry Cathedral
- Coventry Building Society Arena
- Eastnor Castle
- University of Birmingham
- The International Convention Centre





