
Guest house holiday rentals in Cheltenham
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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

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.

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.

Luxury Shepherd's Hut in The Cotswolds
Sans Souci is a bespoke Shepherd's hut, lovingly hand built to an incredibly high spec. Completed in April 2021, it has a double bed and double sofa bed. There is a well-equipped kitchen, a shower room with sink and compost toilet, and a log burning stove. There are far reaching views of the Cotswold hills, which can be taken in from the South-facing deck. Enjoy al fresco meals, cooking over the fire pit in the garden or walks galore in the local countryside.

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.

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.

Larks Nest - your gateway to the Cotswolds
Larks Nest is situated at the edge of the famous village Bourton-on-the-Water one of the most popular and beautiful villages in the Cotswolds with a good selection of shops, restaurants and pubs. The location is the ideal base to explore the Cotswolds with its many attractions.

Beautiful Cotswold Cottage
Situated in the heart of the Cotswolds and being officially recognised as an Area of Natural Outstanding Beauty, this self-contained cottage offers wonderful countryside scenery whilst being only a 10 minute drive from Cheltenham town centre.

Cheltenham's Little Grey House
The Little Grey House is a stylish hidden retreat for those wanting to visit Cheltenham, explore the Cotswolds many beautiful walks and villages or simply for a base during Cheltenham’s infamous Festivals and Racing Events.
Popular amenities for guest house rentals in Cheltenham
Family-friendly guest house rentals

Cub Cottage Nr Broadway Cotswolds Tennis Court

Private Studio- Cirencester

The Jays countryside annexe

The Garden Studio Graywalls Stroud

Meadow Lodge quiet annexe in countryside

Adorable converted stable, close to Evesham town.

A Cosy Cotswold Woodland Cabin

The Annex at The Oaks
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.

Nuthatch Chalet

Small Cotswold cottage / annex

The Hide; a Unique Annex with rural views

Charming guest house in stunning wooded valley

The Annex between the Cotswold Hills
Guest house rentals with a washing machine and dryer

Golden Stone Country Retreat, Cotswolds

Immaculate riverside Cotswold cottage - sleeps 4-6

Gardener's Pavilion | Malvern

Cosy Cotswold Lodge with Hot Tub & Private Garden

Blacklains Annex, Birdlip, Cotswold

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

Anthracite Annex

Greencourt Loft, Cotswold Way, Middleyard, Stroud
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $169 SGD | $164 SGD | $215 SGD | $147 SGD | $153 SGD | $147 SGD | $151 SGD | $164 SGD | $151 SGD | $150 SGD | $147 SGD | $147 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 |
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 $89 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
Destinations to explore
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