
Holiday rentals with outdoor seating near Cheltenham Racecourse
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Top-rated rentals with outdoor seating near Cheltenham Racecourse
Guests agree: these stays are highly rated for location, cleanliness and more.

Luxury Thatched Cotswold Cottage, amazing location
Located in a historic village a stone's throw from Cheltenham's racecourse is our immaculately restored thatched cottage. A choice of 3 pubs, local shop and butcher can be found within walking distance. Ideal for 2 couples sharing or a family with accommodation on 2 floors. Featuring a master suite with roll-top bath and own sitting room which can be converted into a bedroom with a double sofa bed. Downstairs an accessible bedroom with its own separate shower w/c. Full kitchen diner with dog bed

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.

Hunters Lodge Warwickshire
A luxurious self catered barn conversion offering a unique and romantic escape nestled in the picturesque Warwickshire countryside. A place to relax and unwind whether it’s in our gorgeous freestanding bath tub, our 4 poster bed or by putting your feet up in front of the log burner and enjoying the warm and ambient glow. Take a dip in our traditional outdoor spa bath tub situated in your private patio area and watch the sunset across the fields. This is truly a stunning and unforgettable stay.

Regency Apartment | Free Parking | Walk to Town
Ideally located within walking distance of Cheltenham town centre and the racecourse, this recently refurbished apartment offers a comfortable private living space within a large Regency house. Perfect for couples, the apartment sleeps 2, with space for up to 4 using additional single beds if required. Please contact us before booking if you would like the single beds prepared. I co-host with my son Patrick, husband John and daughter Rachel, and we’re always happy to help during your stay.

Studio 77 Cheltenham
You will be very welcome to stay in our brand new and beautifully renovated compact and bijou tiny home which is in an easy walk of Cheltenham Town Centre and the Racecourse. We have created a gorgeous space to the rear of our family home that is completely self contained with its own entrance. Studio 77 comprises of a king size bed, kitchenette area, small seating arrangement and a good sized shower room. There is a small private patio area for guests to enjoy on a sunny evening.

Farm close to Cheltenham with stunning views
Relax in our lovingly-converted dairy on our small working family farm overlooking Cheltenham. Superb views and sunsets from the quiet and private accommodation. Meet our alpacas, donkeys and pygmy goats and enjoy our free range eggs. Walk in our 80 acres of natural hillside, see the wildlife and enjoy the scenery. We are near the Cotswold Way, GWSR Steam Railway and Cheltenham Racecourse, and approx. 2 miles to the centre of Cheltenham - the heart of the Cotswolds.

Stylish apartment in the heart of Cheltenham
A chic stylish one bedroom apartment in a Victorian townhouse in the centre of Cheltenham with FREE PARKING. Perfectly located to experience all Cheltenham has to offer. A short walking distance to festival locations and the most popular bars and restaurants in Montpellier, The Suffolks, Bath Road and the Promenade. The racecourse is a 25 minute walk or 10 minutes by road. An ideal base for those travelling for business or pleasure.

Cotswold77 - Heart of the Cotswolds
Set in the heart of the Saxon village of Winchcombe a beautifully restored and luxuriously furnished Grade II listed cottage set over three floors with a pretty, sunny garden. Glorious countryside, Cotswold country pubs and a Michelin star restaurant all in walking distance. 6 miles from Cheltenham Racecourse and perfect for the Literature, Jazz and Science Festivals in Cheltenham. An Idyllic spot for exploring the Cotswolds!

Prestbury Village Annexe.
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.

Cottage luxe in The Cotwolds
Wycke Cottage welcomes you with unequivocal charm and a little luxe at every turn. Hunker down in style in the picture-perfect Cotswold setting in the heart of Painswick. This 400-year-old cosy cottage, sits opposite the historic church. With stunning sunset views across to the church's beautiful spire and clockface, and its much storied 99 cloud-like yew trees, this stay offers the quintessential Cotswold experience.

Self-contained basement flat in regency home
Refurbished basement flat in grade 2 listed regency terraced house. Central Cheltenham location, walking distance to all local festivals, shopping, pubs and restaurants. Modern, light and spacious accommodation with private access and patio terrace via the bedroom. Good size bathroom with bath and walk-in shower. There is no separate kitchen but an area containing a fridge, microwave, kettle & toaster.

Beautiful Barn in the Cotswolds
Beautifully private converted barn in the heart of Gloucestershire, perfectly situated for Cheltenham Races, the Cotswold Way and Gloucester Rugby as well as all the local town festivals. Dating back to the 1850s and part of the original village Rectory, the barn was converted in 2019 and provides both a light and airy base as well as a cosy and super comfortable retreat. Can sleep up to 4.
Popular amenities for rentals with outdoor seating near Cheltenham Racecourse
House rentals with outdoor seating

Charming Coach House, fab location, highly rated!

Boddington Mill

Bourton on the Water Country Chic OldWorld Cottage

Central Cosy Terraced Victorian 2 Bedroom Cottage

Breathtaking Cotswolds Restored Chapel Valley View

5 Bed House, Sleeps 8, parking, brilliant location

Entire Residential Home - Town Centre, Ideal Races

Beautiful 4 bed house in Cotswolds
Apartment rentals with outdoor seating

Cotswolds Place - stylish design in ❤️ of Broadway

Charming Clifton Flat Driveway Parking, EV Charger

The Quart

The Old Post Office, Central Broadway with Garden

Luxury Apartment with Stunning View

Idyllic Country Retreat in the Forest of Dean

Stylish 2 Bedroom apartment in central Cheltenham

Large Period 2-Bed Apartment Close to Town
Apartment rentals with outdoor seating

Private apartment in stunning historic house

Luxury historic stay, dog-friendly, parking & gdn

Stylish studio apartment in Bourton on the Water

Town Centre Penthouse with Hot Tub 22

Self-contained annex on Cleeve Hill Common.

Stunning Apartment located on the Cotswold Way

Luxury 1 bed, Broadway, Cotswolds. Private parking

Cosy, rural apartment with breakfast hamper
Other holiday rentals with outdoor seating

Quiet grade 1 listed entire cottage in Cotswolds

Luxury Cabin with Hot-Tub & Cold Plunge!

Hobleys Cottage Stanton Nr Broadway

Luxury Barn conversion Cotswold’s with Sauna/Spa

The Old Bakery At The Grange

Wye Valley Escape. Romantic Loft on 40-Acre Estate

Luxury Refurbished 2 Bedroom Regency Apartment

Architectural gem on an acclaimed Cotswold farm /1
Quick stats about holiday rentals with outdoor seating near Cheltenham Racecourse

Total holiday rentals
Explore 30 holiday rentals in Cheltenham Racecourse

Nightly prices starting at
Cheltenham Racecourse holiday rentals start at $77 SGD per night before taxes and fees

Verified guest reviews
Over 1,820 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Cheltenham Racecourse holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Cheltenham Racecourse rentals

4.9 Average rating
Cheltenham Racecourse stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Rentals with breakfast Cheltenham Racecourse
- Pet-friendly rentals Cheltenham Racecourse
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- Rentals with outdoor seating Cheltenham
- Rentals with outdoor seating Gloucestershire
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