
Guesthouse holiday rentals in Cheltenham
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Top-rated Guesthouses in Cheltenham
Guests agree: These guesthouses 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 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

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).

Artist's studio in Edge in stunning countryside.
This is a well equipped studio in the Cotswolds. It's at the end of a singletrack no through road about 1/2 mile from the Cotswold way and at the junction of several footpaths. The nearest towns are Painswick,which is 1 mile away, and Stroud where there is a train station and supermarkets. The studio has a sleeping area with a king size double bed. It is separated by a bookcase from the main living area. where there is also a sofa.

Cleeve Cottage (The Studio)
A small detached studio/annex, in the picturesque village of Bushley, ideal location for anyone looking to have a short break in the countryside just 1.5 miles from the old market town of Tewkesbury and only 20 minutes from Cheltenham so perfect for a weekend at the races. Plenty of stunning rural locations to be explored nearby, with easy access to the beautiful Malvern hills, fantastic for cycling and hiking

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 guesthouses
Family-Friendly guesthouses

Doe Bank, Great Washbourne

Private Studio- Cirencester

Cosy old stone loggia, in village - close to pub

Charming Cotswold Stable Conversion.

Cotswold village location- Detached guest house

RandwickStudio

The Cider Press with Games Room

Charming, detached, converted stable in Evesham.
Guesthouses with a patio

Prestbury Village Annexe.

Self contained annex adjoining a family home.

The Little House

Adorable One Bedroom Cotswold Studio

Cotswolds Cool - The Hayloft

Gorgeous 1 Bed Cotswold rural studio. With Parking

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

Scenic 2 Bed Lodge with hot tub and indoor pool

Cosy Cotswold Lodge with Hot Tub & Private Garden

Gardener's Pavilion | Malvern

Blacklains Annexe, Birdlip, Cotswold

Self-contained property in Rodborough

Anthracite Annexe

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 | $193 NZD | $186 NZD | $255 NZD | $200 NZD | $209 NZD | $200 NZD | $205 NZD | $222 NZD | $205 NZD | $215 NZD | $217 NZD | $188 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 $104 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
Destinations to explore
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- Cotswolds AONB
- University of Oxford
- Blenheim Palace
- Wye Valley Area of Outstanding Natural Beauty (AONB)
- Silverstone Circuit
- Lower Mill Estate
- Cheltenham Racecourse
- West Midland Safari Park
- Cadbury World
- Sudeley Castle
- Ludlow Castle
- Waddesdon Manor
- Bath Abbey
- No. 1 Royal Crescent
- Coventry Cathedral
- Puzzlewood
- Shakespeare's Birthplace
- Bowood House and Gardens
- Hereford Cathedral
- Royal Shakespeare Theatre
- Dyrham Park
- Lacock Abbey
- Manor House Golf Club
- Painswick Golf Club




