Family-friendly vacation rentals in Winchcombe

Little Nook Cottage - Cosy & Large Garden

Located in the heart of Winchcombe with far reaching views over the rolling Cotswold hills, Little Nook Cottage is a charming bolt hole, perfect for couples or a small family from which to explore the Cotswolds. You will find beautifully crafted beams and original stone floors paired with all the luxuries you need for a relaxing break. Featuring a cosy living/dining room with wood burning fire, a super comfy double room and even a dedicated work space should you wish to work away from home!

Kitchen · Indoor spaces · Outdoor spaces

Beam House, Winchcombe, sleeps 6 + 2

We don't just offer you somewhere to sleep; at Beam House you can indulge in all the Cotswolds and Cheltenham have to offer knowing you can return to a uniquely styled period house in Winchombe's historic Gloucester Street. Expect soft cotton linens, a wood burning stove, Farrow and Ball paint, exposed beams and stone and oak floors. We offer a unique and stylish retreat ideal for relaxing and exploring. We can host 6 (1 king, 2 double) plus 2 (a sofa bed is available in the drawing room).

Indoor spaces · Family · Laundry

Cosy Cotswold Cottage in the centre of Winchcombe

Vineyard street is an unrivaled position in Winchcombe, a unique town in all it has to offer, where visitors are welcomed and quickly feel like locals and get to enjoy a real part of Cotswolds Life. No. 5 is a traditional cosy cottage, decorated and furnished to a high standard to ensure our guests comfort and needs. We are local owners and are on hand with any questions and to offer recommendations to make the most of your visit. Secure garden, dogs are very welcome, also allowed in pubs

Kitchen · Indoor spaces · Getting around

Luxury Central, Dog friendly, King Bed, Log fire

The Bolt Hole is a charming, refurbished, dog-friendly, Cotswold stone cottage, central to pubs and cafes - Late check-out 11 am + NO cleaning or Airbnb fees - Easy FREE on-street parking - Log burner + dishwasher + Washing Machine - V Comfortable UK King mattress - Fantastic walks from doorstep - En-suite: new large shower 🚿+ roll-top bath 🛀 - Smart TV - Cot and highchair Nestled in the heart of stunning Winchcombe, steps from pubs, restaurants, cafes, and historic Sudeley Castle.

Family · Kitchen · Comfort

Luxury Cotswolds Cottage with Hot Tub

Escape to our luxurious Cotswolds holiday cottage with a hot tub! Located in the enchanting Cotswold region, our snug-luxe cottage offers the perfect break. With a landscaped garden and proximity to Cheltenham, it's ideal for race enthusiasts and explorers. Experience an unforgettable weekend getaway, family holiday, or celebration with friends in style and comfort. Book now to indulge in the beauty of the Cotswolds and enjoy relaxation, scenic trails, and the charm of Cotswolds living.

Family · Indoor spaces · Hot tub

Cosy Cotswold Cottage near Cheltenham

Our 200 year old cottage provides the perfect getaway for walkers, cyclists, families or those just wanting some time to unwind and explore the beautiful Cotswold country side. Although the accommodation has been recently refurbished with a new kitchen and bathroom it still retains a wealth of original features including exposed oak beams, stone walls and wood floors. Pubs, cafes, restaurants, shops, Sudely Castle are within walking distance. Cheltenham race course is 6 miles away.

Indoor spaces · Kitchen · Backyard

4 Vineyard Street

A character filled Cotswold stone cottage including an indoor log burner and a patio with a garden to the rear of the cottage with a coal BBQ which allows for outdoor dining during the summer. Two double bedrooms allow plenty of space for families or friends to holiday in this stylish and welcoming home. This central location means all local amenities are just yards from your front door. See our Cotswold Escapes website and socials for more information and pictures

Indoor spaces · Kitchen · Bathroom

The Feathered Nest an idyllic Cotswolds escape.

Nestled in the heart of historic Winchcombe, The Feathered Nest offers a welcoming escape in the beautiful North Cotswolds. Set on picturesque Vineyard Street, this lovingly restored former wool cottage blends timeless character with modern comforts. Thoughtfully renovated by the owners this the boutique two-bedroom home features stylish furnishings and all the contemporary amenities you need for a relaxing stay. Next availability from 1st October.

Kitchen · Indoor spaces · Walkability

Muir Cottage in the Cotswolds

Muir Cottage has been converted from an 18th Century barn to a design inspired by the Arts and Crafts Movement that established in the Cotswolds in the 19th Century, resulting in an array of stone mullioned windows, exposed beams and period furnishings. It is beautifully situated in a hidden coombe on the leeward side of the Cotswolds highest hill, yet only minutes from Winchcombe, a classic Cotswold "wool town" with excellent shops and restaurants.

Kitchen · Indoor spaces · Long stay

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!

Family · Kitchen · Parking

'Fifteen off the Green'- 1 Bedroom Cotswolds Home

Nestled on a close next to a peaceful tree-strewn lawn lies ‘Fifteen off the Green’. This fun and unique one bedroom home offers its guests the perfect balance of luxury and design whilst adding all creature comforts to make you feel right at home. Newly refurbished and designed with couples in mind, this home has everything you could need to cook up a storm or just to relax and unwind after a busy day exploring the Cotswolds.

Indoor spaces · Kitchen · Nearby

Kingfisher Cottage, Disabled Friendly, Cotswolds

Nestled in the wonderful market town of Winchcombe, this relaxing retreat in the heart of the Cotswolds is the perfect base for a family or group getaway to this beautiful part of the world. Experience sweeping countryside views and a tranquil garden with gentle babbling stream winding alongside it. Discover local highlights like Sudeley Castle, Broadway and Cheltenham Racecourse or explore the wider Cotswolds.

Family · Indoor spaces · Cleanliness