Vacation rentals in Upton Saint Leonards

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Top-rated vacation rentals in Upton Saint Leonards

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Guest favorite

Cottage in Painswick

4.96 out of 5 average rating, 147 reviews

Cosy Cotswold Cottage in the heart of Painswick.

This pretty, cotswold stone cottage in the heart of Painswick has been newly renovated, with a modern county feel. With feature fireplaces and a wood burner It is the perfect base for exploring the Cotswolds and is only a 20 minute drive to Cheltenham. The cottage is only a couple of minutes walk from the local pub and the other restaurants in the village, including the Painswick Hotel, which serves afternoon tea, cocktails and offers a beautiful restaurant. Local shop is a a few meters away.

Dec 9 – 16

G$39,096 GYD per night

Guest favorite

Guest suite in Painswick

4.94 out of 5 average rating, 337 reviews

Painswick is Paradise Guest Suite

A lot to enjoy - walk the Cotswold Way and Laurie Lee trail in Slad Valley. Visit Cheltenham races, the popular Stroud Farmers Market and Five Valleys shopping centre selling street food. Discover the picturesque canal and cycle trail. Enjoy a pint in the Woolpack at Slad, an ice cream on Minchinhampton Common. Easily reached - Forest of Dean, Bourton-on-the-Water, Cotswold Water Park, Brecon Beacon. Painswick- AONB - its churchyard with 99 yew tres, golf course, pub and several eateries.

Oct 7 – 14

G$17,691 GYD per night

Guest favorite

Tiny home in Witcombe

4.88 out of 5 average rating, 482 reviews

Little Knapp on the Cotswold Way

Snug space ideal for relaxing getaways. Set in area of outstanding natural beauty. Perfect for couples keen to explore the Cotswolds with direct access to the Cotswold way. It's a quirky small space. Intended as a great escape, there is WiFi but no TV. Dogs: As space limited 1 w-behaved dog welcome (+ £10). Sofabed: Please request bedding (+£10 charge) or bring own for free. NB Bathroom space is limited, stairs may be tricky for less mobile, roof terrace is private but overlooked by our house.

Sep 25 – Oct 2

G$22,571 GYD per night

Guest favorite

Condo in Painswick

4.97 out of 5 average rating, 157 reviews

Stunning one bedroom Cotswold loft apartment

Charming apartment with stunning views over orchard and fields in perfect location for both Painswick - Queen of the Cotswolds - and the Slad valley, home to poet Laurie Lee. Award winning pubs nearby. In the grounds of seventeenth century Turnstone House, listen to the owls, watch the buzzards and spot the deer. Enjoy a drink as the sun sets behind the iconic Painswick church steeple. Delicious breakfast. Microwave/mini-fridge/hob. Additional bed, pets by arrangement - additional £15 pet fee.

Mar 4 – 11

G$34,037 GYD per night

Guest favorite

Cottage in Painswick

5.0 out of 5 average rating, 133 reviews

Quiet grade 1 listed entire cottage in Cotswolds

A bright and recently modernised grade 1 listed Cotswold stone cottage, 100 yards from the Cotswold Way with breathtaking views down the Stroud Valley, its own parking and secluded outdoor eating. Filled with natural light, it is very peaceful and extremely comfortable with luxury bedding (super king or twin bed) and kitchen. An idyllic spot for walking, cycling, exploring the local scenery or simply escaping the city Painswick is 10 minutes from Stroud ( 87 mins hourly train to London).

Jan 15 – 22

G$40,865 GYD per night

Guest favorite

Tiny home in Gloucestershire

4.93 out of 5 average rating, 499 reviews

The Garden House in Kingsholm, Gloucester

The Garden House is a lovely single room annex with independent access, en-suite bathroom and shower. Light, cosy, and simply furnished, set in the garden of a residential home near the centre of Gloucester, it's a quiet space to relax or work. Driveway parking available. A two-minute walk to the famous Kingsholm rugby stadium and food shops, ten minutes to city centre, bus and train stations, cathedral, Quays shopping outlet, restaurants and historic docks. Easy bus route to Cheltenham.

Jun 5 – 12

G$10,495 GYD per night

Guest favorite

Guest suite in Sheepscombe

5.0 out of 5 average rating, 211 reviews

Idyllic rural location in Sheepscombe village

A self contained annexe on a working small holding which has recently been refurbished to a high standard. It is overlooking the unique village of Sheepscombe with fantastic panoramic views over the village and surrounding National Trust beechwoods. This rural retreat is a walkers paradise, dog friendly with close access into the woods behind and near to the Laurie Lee way in the Slad Valley. Stroud, Cheltenham, Cirencester and Gloucester are a short drive away. An idyllic quiet get away.

Nov 26 – Dec 3

G$29,613 GYD per night

Guest favorite

Guest suite in Hucclecote

4.88 out of 5 average rating, 188 reviews

Neunundzwanzig. Self contained private suite.

Neunundzwanzig Is a totally self contained purpose built studio apartment that is light warm and airy with private access. Off road parking and private rear courtyard. Based in the village of Hucclecote near Cheltenham and Gloucester in a quiet and pleasant location and on the doorstep to the Cotswolds. Ideal for those wishing to explore the area or business people needing easy access to Gloucester business park and on the ring road for easy access to GCHQ on the outskirts of Cheltenham.

Sep 24 – Oct 1

G$19,564 GYD per night

Guest favorite

Condo in Gloucestershire

4.82 out of 5 average rating, 251 reviews

Spacious Apartment Close To Gloucester Quays/Docks

Exclusively for adults, this warm, light and airy apartment is situated in a quiet grade II listed Georgian house, with its own private car park. With a well equipped kitchen and recently refurbished throughout and featuring a classic king size four poster bed. Only minutes walk to the city centre, historic Docks, Gloucester Quays retail park, restaurants, bars and cinema. Ideally located for visiting Gloucester’s famous Cathedral, museums and for attending all Gloucester’s festivals.

Jul 5 – 10

G$19,927 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.

Oct 17 – 24

G$27,620 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 19 – 26

G$27,207 GYD per night

Guest favorite

Guesthouse in Standish

4.98 out of 5 average rating, 490 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.

Oct 2 – 9

G$27,228 GYD per night