
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.

Cosy Cotswold Lodge with Hot Tub & Private Garden
April Cottage Lodge is a stylish & spacious 1 Bedroom, spotlessly clean, very well appointed holiday let in the North Cotswolds. We offer private accommodation with super views, good WiFi, off road parking & private garden with a hot tub, patio furniture & BBQ. A fantastic base to explore many famous Cotswold Villages, walk stretches of the Cotswold Way, towns & landmarks of Gloucestershire, Warwickshire, Oxfordshire & Worcestershire. Within walking distance of the local pub, shop & GWS Railway.

Golden Stone Country Retreat, Cotswolds
This quirky, stone-built barn conversion is set in the picturesque village of Ampney St. Mary, near Cirencester, in the heart of the stunning Cotswolds landscape. Generous open plan living in a detached apartment with double bed, lounge area, beautiful kitchen/dinning area and ensuite bathroom. Underfloor heating throughout so suitable for all seasons. Ideal for holidaymakers looking for a tranquil base from which to explore the AONB or individuals seeking a quiet, secluded space to work/study.

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.

Adorable One Bedroom Cotswold Studio
We hope to create a calm, friendly and accommodating environment for you to stay in our latest labour of love. Life is peaceful and quite here in our deceptively secluded spot in the hamlet of Watledge, on the Cotswold Way. We are within easy walking distance of the vibrant town of Nailsworth, as well as Amberley and Minchinhampton Common, with short drives to Cirencester, Cheltenham, Stroud, Tetbury, Bath, Badminton and Gatcombe. Come, relax and enjoy the Cotswolds.

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

The Small House with a Big Welcome

Modern Studio in Long Ashton

The Hut and Tub

Meadow Lodge quiet annexe in countryside

Charming barn in Cotswolds AONB near Burford

A Cosy Cotswold Woodland Cabin

The Annex at The Oaks
Guest house rentals with a patio

Little Rosewood is a Cosy Cotswold Retreat

Little Simplicity Detached Annexe House in Bristol

Central Stow: Private Studio with Garden & Parking

Self contained annex with own entrance & parking.

Nuthatch Chalet

The Yard: Rustic guest house in Malvern

Small Cotswold cottage / annex

The Hide; a Unique Annex with rural views
Guest house rentals with a washing machine and dryer

Immaculate riverside Cotswold cottage - sleeps 4-6

Little Bulpits

Scenic 2 Bed Lodge with hot tub and indoor pool

Gardener's Pavilion | Malvern

Blacklains Annex, Birdlip, Cotswold

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 | $165 SGD | $216 SGD | $148 SGD | $154 SGD | $148 SGD | $152 SGD | $165 SGD | $152 SGD | $151 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 |
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
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- Cotswolds AONB
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- Cheltenham Racecourse
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