
Guesthouse vacation rentals in Cheltenham
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Top-rated guesthouse rentals in Cheltenham
Guests agree: these guesthouse rentals 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

The Annex at Stonehaven
The Annex offers dog friendly accommodation with plenty of relaxing 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 a fenced orchard at the back. We are between Cheltenham, Gloucester and Tewkesbury so perfect for exploring these towns. Mon-Fri your host grooms dogs in a room connected to the Annex. Dogs or driers might be heard during the day on weekdays.

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 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

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.

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.
Popular amenities for Cheltenham guesthouse rentals
Family-friendly guest house rentals

Seedwood Barn

Private Studio- Cirencester

Cosy old stone loggia, in village - close to pub

The Small House with a Big Welcome

B&B in Beautiful Cotswold Annex

A Cosy Cotswold Woodland Cabin

Detached Annex in idyllic Countryside

Hollys Cottage
Guest house rentals with a patio

Little Rosewood is a Cosy Cotswold Retreat

Garden Annex Dormston

Adorable One Bedroom Cotswold Studio

Hathaways, RSC, Views, Parking, Walk to Town.

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
Guest house rentals with a washer and dryer

Golden Stone Country Retreat, Cotswolds

Cosy Cotswold Lodge with Hot Tub & Private Garden

Gardener's Pavilion | Malvern

Blacklains Annexe, Birdlip, Cotswold

Self-contained property in Rodborough

Anthracite Annexe

Greencourt Loft, Cotswold Way, Middleyard, Stroud

Little gem at foot of Malvern Hills
When is the best time to visit Cheltenham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$23,165 GYD | G$22,330 GYD | G$30,678 GYD | G$23,999 GYD | G$25,043 GYD | G$23,999 GYD | G$24,626 GYD | G$26,712 GYD | G$24,626 GYD | G$25,878 GYD | G$26,086 GYD | G$22,539 GYD |
| 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 vacation rentals
Explore 20 vacation rentals in Cheltenham

Nightly prices starting at
Cheltenham vacation rentals start at G$12,521 GYD 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 vacation 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
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- Cotswolds AONB
- Oxford University
- Blenheim Palace
- Silverstone Circuit
- Lower Mill Estate
- Cheltenham Racecourse
- West Midland Safari Park
- Cadbury World
- Sudeley Castle
- Ludlow Castle
- Waddesdon Manor
- Bath Abbey
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- Puzzlewood
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- Painswick Golf Club
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