Guesthouse vacation rentals in Cheltenham

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Top-rated guesthouse rentals in Cheltenham

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Guest favorite

Guesthouse in Cheltenham

4.95 out of 5 average rating, 219 reviews

Boutique Cotswold bolt hole - Ford Manor Cottage

Entire cottage set in grounds of owner's home with own gravelled and gated parking area, in the heart of the Cotswolds and National Hunt racing. Luxury open plan living/bedroom (approx. 25 sq m) which is light and airy with 4 post bed , well equipped galley kitchen and wet room. Complete privacy. Ideal retreat for short or long stays. A great base for walking and exploring the Cotswolds, with the Cotswold Way on the doorstep, Sudeley Castle a few miles away and Daylesford a 15 minute drive.

Jul 9 – 16

G$26,821 GYD per night

Guest favorite

Guesthouse in Leigh

4.92 out of 5 average rating, 155 reviews

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.

Oct 8 – 15

G$22,886 GYD per night

Guest favorite

Guesthouse in Twyning

4.78 out of 5 average rating, 235 reviews

The groomsroom

Ex - grooms room, in the grounds of a beautiful country mansion. Self contained bedsit/studio with parking. Stabling available at extra cost if you want to turn this into an equine holiday! 4 miles from Tewkesbury and on the outskirts of Twyning, a beautiful location for a country break. Seasonal breakfast ingredients provided, but we are afraid you'll have to cook them yourself! Tea and coffee making facilities also provided. Fresh milk and bread will be in the fridge when you arrive.

Dec 17 – 24

G$12,087 GYD per night

Guest favorite

Guesthouse in Minchinhampton

4.98 out of 5 average rating, 262 reviews

The Cotswolds Couples' Getaway

In the centre of beautiful Minchinhampton, this detached cosy cottage is open plan in design and tastefully renovated throughout with plenty of modern conveniences. Set in our quiet pretty garden, and with on-site parking + Type 2 EV charger, a perfect getaway. The space is safe for a couple, equipped for living, and it is easy to remain quite isolated from the busy world. As hosts, we are right next door for queries and information. Please read our reviews to see why people book.

Aug 13 – 20

G$27,498 GYD per night

Guest favorite

Guesthouse in Eckington

4.99 out of 5 average rating, 149 reviews

Newly restored cottage with views of Bredon Hill

Cedar Cottage is a brand new 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, an excellent village shop and a hairdresser's within walking distance. Perfectly situated for easy access to Cheltenham Festivals, Upton-upon-Severn and the Cotswolds. Secure bike storage offered.

Jun 20 – 27

G$22,556 GYD per night

Guest favorite

Guesthouse in Cranham

4.99 out of 5 average rating, 153 reviews

The Organic Cotswolds Cowshed

Welcome to the 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 (Covid regulations allowing!) 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 regular cleaning chemicals and sprays. We also try to be as environmentally minded as possible.

Sep 3 – 10

G$27,087 GYD per night

Guest favorite

Guesthouse in Gloucester

4.96 out of 5 average rating, 339 reviews

The Hut and Tub

Cosy Centrally Heated Shepherds Hut With luxury hot tub In Quiet Rural Area The perfect 'country getaway' for two people. This small shepherds hut is tucked away in the heart of a quiet Gloucestershire village situated in the corner of our garden but completely private and not overlooked with its own decking and luxury hot tub overlooking fields and farmland. The river Severn is less than a mile away which has a footpath all the way to Tewkesbury and nearby pubs.

Oct 7 – 14

G$30,049 GYD per night

Guest favorite

Guesthouse in Standish

4.98 out of 5 average rating, 489 reviews

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.

Mar 3 – 10

G$28,518 GYD per night

Guest favorite

Guesthouse in Withington

4.99 out of 5 average rating, 257 reviews

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.

Jan 22 – 29

G$26,854 GYD per night

Guest favorite

Guesthouse in Cheltenham

4.97 out of 5 average rating, 232 reviews

Private Annexe - double bedroom with en-suite

A detached annexe in Cheltenham with double bedroom and en-suite bathroom, this newly refurbished 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.

Sep 15 – 22

G$19,016 GYD per night

Guest favorite

Guesthouse in Cheltenham

4.98 out of 5 average rating, 114 reviews

Leighterton, a beautiful Cotswold hideaway

Leighterton is a new bolthole in the heart of the Cotswold. The small, but perfectly formed, annex offers a beautifully designed, well-equipped space to stay. Surrounded by fields guests can enjoy walks, cycling and exploring neighboring villages. We are also perfectly located for guests of weddings at Cripps and Stone Barn. Located in a separate building next to the main house you have both security and privacy.

Jun 18 – 25

G$25,526 GYD per night

Guest favorite

Guesthouse in Worcestershire

4.95 out of 5 average rating, 183 reviews

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

Oct 2 – 9

G$21,826 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Cheltenham guesthouse rentals

Kitchen

Wifi

Free parking on premises

Air conditioning

Family-friendly guest house rentals

Guest favorite

Guesthouse in Randwick

4.93 out of 5 average rating, 287 reviews

Bright, airy Annex in village with stunning views

Aug 25 – Sep 1

G$19,472 GYD per night

Guest favorite

Guesthouse in Ampney Crucis

4.94 out of 5 average rating, 619 reviews

B&B in Beautiful Cotswold Annex

Sep 25 – Oct 2

G$24,812 GYD per night

Guest favorite

Guesthouse in Cirencester

4.97 out of 5 average rating, 410 reviews

Cirencester- detached annexe with private terrace

Feb 8 – 15

G$31,145 GYD per night

Guest favorite

Guesthouse in France Lynch

4.96 out of 5 average rating, 273 reviews

The Old Greenhouse. France Lynch, Stroud

Nov 25 – Dec 2

G$20,487 GYD per night

Guest favorite

Guesthouse in Cirencester

4.95 out of 5 average rating, 228 reviews

Cotswold Studio, Cirencester

Nov 28 – Dec 5

G$28,697 GYD per night

Guest favorite

Guesthouse in Severn Stoke

4.97 out of 5 average rating, 332 reviews

Detached Annex in idyllic Countryside

Jun 15 – 22

G$18,330 GYD per night

Guest favorite

Guesthouse in Broadway

4.91 out of 5 average rating, 171 reviews

Lola's Cottage

Apr 5 – 12

G$37,224 GYD per night

Guest favorite

Guesthouse in Bridstow

4.95 out of 5 average rating, 617 reviews

The Annex at The Oaks

Nov 6 – 13

G$27,672 GYD per night

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Guest house rentals with a patio

Guest favorite

Guesthouse in Leigh

4.9 out of 5 average rating, 105 reviews

Stunning rural retreat perfect for couples & dogs

Sep 28 – Oct 5

G$24,604 GYD per night

Guest favorite

Guesthouse in Amberley

5.0 out of 5 average rating, 123 reviews

Adorable One Bedroom Cotswold Studio

Jan 28 – Feb 4

G$28,491 GYD per night

Guest favorite

Guesthouse in Sedgeberrow

4.93 out of 5 average rating, 107 reviews

The Annex between the Cotswold Hills

Apr 11 – 18

G$22,738 GYD per night

Guest favorite

Guesthouse in Wiltshire

4.98 out of 5 average rating, 126 reviews

Gorgeous 1 Bed Cotswold rural studio. With Parking

Oct 28 – Nov 4

G$21,497 GYD per night

Guest favorite

Guesthouse in Horsley

4.9 out of 5 average rating, 106 reviews

Charming guest house in stunning wooded valley

Mar 29 – Apr 5

G$22,666 GYD per night

Guest favorite

Guesthouse in Oxfordshire

4.95 out of 5 average rating, 120 reviews

Adorable 1 bedroom guest house with hot tub

Oct 8 – 15

G$27,567 GYD per night

Guest favorite

Guesthouse in Gloucestershire

4.93 out of 5 average rating, 44 reviews

Two Double Bedrooms Guest House with EV Charging

Sep 25 – Oct 2

G$34,808 GYD per night

Guest favorite

Guesthouse in Twigworth

5.0 out of 5 average rating, 14 reviews

The Annex at Stonehaven

Aug 9 – 16

G$21,645 GYD per night

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Guest house rentals with a washer and dryer

Guest favorite

Guesthouse in Gloucester

4.96 out of 5 average rating, 213 reviews

Blacklains Annexe, Birdlip, Cotswold

Dec 26 – Jan 2

G$69,237 GYD per night

Guest favorite

Guesthouse in Cheltenham

4.98 out of 5 average rating, 193 reviews

Cosy Cotswold Lodge with Private Garden & Hot Tub

Aug 5 – 12

G$41,890 GYD per night

Guest favorite

Guesthouse in Kempsford

4.99 out of 5 average rating, 287 reviews

Meadow Lodge quiet annexe in countryside

Jun 21 – 26

G$25,789 GYD per night

Guest favorite

Guesthouse in Bledington

4.99 out of 5 average rating, 141 reviews

Cotswolds Getaway in a luxury oak cabin.

Oct 8 – 15

G$38,259 GYD per night

Guest favorite

Guesthouse in Worcestershire

4.88 out of 5 average rating, 302 reviews

Spacious, beautiful garden flat in the Malverns

Oct 11 – 18

G$22,852 GYD per night

Guest favorite

Guesthouse in Berrow

4.95 out of 5 average rating, 165 reviews

Little gem at foot of Malvern Hills

Feb 17 – 24

G$37,224 GYD per night

Guest favorite

Guesthouse in Thornbury

4.95 out of 5 average rating, 113 reviews

Lavender Annex

Jun 13 – 20

G$16,574 GYD per night

Guest favorite

Guesthouse in Whitfield

4.96 out of 5 average rating, 105 reviews

Scenic 2 Bed Lodge with hot tub and indoor pool

Apr 19 – 26

G$48,453 GYD per night

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Quick stats about guesthouse rentals in Cheltenham

Total rentals
20 properties
Local attractions
Cheltenham Racecourse, Pittville Park, and Montpellier Gardens
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
20 properties include access to wifi
Total number of reviews
2K reviews
Nightly prices starting at
G$12,538 GYD before taxes and fees

Guesthouse vacation rentals in Cheltenham

Top-rated guesthouse rentals in Cheltenham

Vacation rentals for every style

Apartments

Houses

Cottages

Popular amenities for Cheltenham guesthouse rentals

Family-friendly guest house rentals

Guesthouse in Randwick

Guesthouse in Ampney Crucis

Guesthouse in Cirencester

Guesthouse in France Lynch

Guesthouse in Cirencester

Guesthouse in Severn Stoke

Guesthouse in Broadway

Guesthouse in Bridstow

Guest house rentals with a patio

Guesthouse in Leigh

Guesthouse in Amberley

Guesthouse in Sedgeberrow

Guesthouse in Wiltshire

Guesthouse in Horsley

Guesthouse in Oxfordshire

Guesthouse in Gloucestershire

Guesthouse in Twigworth

Guest house rentals with a washer and dryer

Guesthouse in Gloucester

Guesthouse in Cheltenham

Guesthouse in Kempsford

Guesthouse in Bledington

Guesthouse in Worcestershire

Guesthouse in Berrow

Guesthouse in Thornbury

Guesthouse in Whitfield

Quick stats about guesthouse rentals in Cheltenham

Total rentals

Local attractions

Popular amenities

Wifi availability

Total number of reviews

Nightly prices starting at

Destinations to explore