Family-friendly vacation rentals in Winchcombe

4.87 out of 5 average rating, 238 reviews

Penny Cottage - Cosy Cotswold cottage

Penny Cottage is in the heart of the former Saxon town of Winchcombe. It is a traditional Cotswold cottage with a working inglenook fireplace. It is on the Cotswold Way and has access to miles of country walks. Sudeley Castle, the resting place of the only Queen of England to be buried outside a royal palace, is within walking distance. A variety of pubs and restaurants can all be found within a 5 minute walk. The town also boasts a variety of independent shops, and two small supermarkets.

KitchenIndoor spacesValue

The living area features a cozy seating arrangement with a neutral-toned sofa and decorative cushions. A natural woven pendant light hangs above, illuminating the space. A rustic coffee table sits on textured flooring, accompanied by warm tones and a charming wreath adorning the entrance.

4.98 out of 5 average rating, 260 reviews

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!

KitchenFamilySleep quality

A comfortable living space features a gray sofa paired with a rustic wooden bench. A stone fireplace with a wood-burning stove is framed by an elegant circular mirror, while warm lighting hangs from the ceiling, creating a cozy ambiance. A television stands on a wooden dresser nearby.

4.93 out of 5 average rating, 164 reviews

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).

FamilyIndoor spacesComfort

The charming exterior of a stone cottage is depicted, showcasing a green door under a decorative canopy. Flanking the entrance are small potted plants. A friendly dog is seated on the doorstep, adding a welcoming touch to the quaint facade.

4.88 out of 5 average rating, 156 reviews

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

KitchenIndoor spacesBiking

4.89 out of 5 average rating, 267 reviews

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.

FamilyIndoor spacesDecor

A charming stone cottage stands proudly under a clear blue sky, featuring a symmetrical facade with white-framed windows. A neatly landscaped garden with low hedges and shrubs frames the entrance, while a path leads to the front door.

4.96 out of 5 average rating, 175 reviews

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.

Indoor spacesKitchenShared spaces

A stone wall surrounds a rustic fireplace, where a log burner emits a warm glow. A polished wooden mantel holds decorative items and five candles. A bottle of champagne rests in an ice bucket beside two glasses, enhancing the cozy ambiance of the sitting room.

4.89 out of 5 average rating, 135 reviews

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.

FamilyKitchenBathroom

A charming row of Cotswold stone cottages is nestled beside a tree-lined pathway. The cottages display traditional slate roofs and white-framed windows, with vibrant flowers and climbing plants adorning their stone walls, creating an inviting residential atmosphere.

4.93 out of 5 average rating, 127 reviews

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

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A stone wall is adorned with vibrant red and pink roses, adding a touch of natural beauty. The wall borders a gravel pathway leading to the entrance. Lush greenery surrounds the flowers, creating a serene atmosphere in the outdoor space.

4.91 out of 5 average rating, 191 reviews

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.

FamilyIndoor spacesBackyard

A modern kitchen features sleek grey cabinetry and polished white countertops. A stainless steel sink is complemented by a built-in wine fridge. Nearby, large glass doors open to a garden area, allowing natural light to illuminate the space. A decorative welcome sign is placed on the countertop.

4.92 out of 5 average rating, 571 reviews

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!

Indoor spacesFamilyWifi

The master bedroom features a king size headboard with a woven design. Two decorative pillows in contrasting patterns rest against the crisp white bedding. Above, framed artwork, including a tiger and a whimsical cat, adorns the wall, complemented by soft bedside lamps.

5.0 out of 5 average rating, 174 reviews

'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.

KitchenIndoor spacesCheck-in

4.95 out of 5 average rating, 102 reviews

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.

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Popular amenities for Winchcombe family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Superhost

The traditional farmhouse is depicted from the exterior, showcasing its stone façade and distinctive architecture. A well-maintained garden is visible in the foreground, while the blue sky and scattered clouds complement the overall setting.

Home in Cheltenham

Traditional 6br farmhouse

FamilyKitchenNearby

4.85 out of 5 average rating, 110 reviews

4.94 out of 5 average rating, 197 reviews

Home in Boddington

Boddington Mill

FamilyIndoor spacesCondition

5.0 out of 5 average rating, 193 reviews

The exterior of a Georgian house features a white facade with large windows and a welcoming entrance. A paved pathway leads to the front door, flanked by vibrant flower beds filled with blooming roses and other colorful plants, enhancing the serene ambiance.

Home in Tewkesbury

Attractive Period House with breath-taking views

FamilyIndoor spacesGetting around

4.99 out of 5 average rating, 586 reviews

A wood-clad cabin is nestled among trees, featuring rounded architecture and large windows. A wooden terrace with two chairs invites relaxation. A hot tub is positioned nearby, surrounded by nature and colorful autumn foliage.

Hut in Avon Dassett

Dassett Cabin - retreat, relax, romance, rewild

KitchenFamilyComfort

4.97 out of 5 average rating, 292 reviews

A private patio area features a round wooden table with four folding chairs, surrounded by colorful flowers. A wood-fired hot tub is visible nearby, overlooking a scenic view of lush hills and greenery, under a bright sky with scattered clouds.

Cottage in Mitcheldean

Romantic Idyllic Nuthatch Cottage with Hot Tub

Indoor spacesKitchenComfort

4.93 out of 5 average rating, 101 reviews

A charming cottage is set amidst lush greenery, featuring a private hot tub in the garden area. The exterior showcases warm stone walls, multiple windows, and a welcoming entryway. Surrounding the cottage, wooden fencing and landscaped walks can be seen, leading to the tranquil landscape beyond.

Home in Elmley Castle

Lavender Cottage Cotswold Farm Retreat

FamilyKitchenLocation

4.98 out of 5 average rating, 116 reviews

A spacious countryside home with stone and brick façades is set against a backdrop of rolling hills. A large parasol shades seating in the landscaped garden, surrounded by greenery. The property features a gravel pathway leading towards the rear garden area, enhancing outdoor relaxation.

Home in Grafton

Beautiful Cotswold Farmhouse with Hot tub

KitchenFamilyLocation

Shepherd’s hut in Toddington

A charming yellow Shepherd's Hut is shown with a welcoming entrance featuring dual white doors and a small staircase. Decorative outdoor lighting is installed beside the door, framed by lush greenery and a wooden fence, inviting guests to explore its cozy interiors.

Cosy Shepherds Hut with Wood-Fired Hot Tub

Indoor spacesKitchenLocation

4.97 out of 5 average rating, 128 reviews

Family- and pet-friendly home rentals

A cozy living area is highlighted by a stone fireplace featuring a log burner. Two comfortable armchairs are positioned near a coffee table, adorned with decorative items. Soft lighting is provided by a lamp, enhancing the warm atmosphere of the space.

4.93 out of 5 average rating, 207 reviews

Thimble Cottage. Winchcombe

FamilyIndoor spacesBackyard

A spacious bedroom features a wooden headboard against a neutral wall. Two bedside lamps provide soft lighting beside the bed, which is adorned with decorative pillows. A large window with curtains allows natural light to enter, and neatly arranged towels are displayed on a nearby surface.

4.86 out of 5 average rating, 598 reviews

Apple Tree Cottage, 2 bedroom (double & king beds)

KitchenIndoor spacesParks

4.91 out of 5 average rating, 129 reviews

An inviting exterior of the Royal Oak pub features warm lighting against the stone façade, showcasing large windows. A distinctive tree sculpture stands in the foreground, surrounded by landscaped greenery. A sign identifying the pub can be seen near the entrance.

Condo in Winchcombe

The flat over the pub!

KitchenFamilyDecor

Guesthouse in Cleeve Hill

A well-lit two-story living area is shown, featuring a wooden staircase leading to a lofted bedroom. Large skylights above provide natural light. A built-in bookshelf and a television are visible on the lower level, alongside comfortable seating arranged for relaxation.

Chapel End

KitchenIndoor spacesNearby

4.99 out of 5 average rating, 191 reviews

The exterior of the cottage showcases a brick and painted façade under a gabled roof. A gravel pathway leads to a large oak front door. Natural landscaping surrounds the property, enhancing the welcoming appearance of this recently renovated building.

5.0 out of 5 average rating, 200 reviews

Cider Mill Cottage, Winchcombe

Indoor spacesKitchenTV

Shepherd’s hut in Winchcombe

Luxury Shepherds Hut with Private Bath Hut

KitchenIndoor spacesSleep quality

4.99 out of 5 average rating, 104 reviews

4.93 out of 5 average rating, 133 reviews

A modern kitchen features a large island with four blue bar stools and granite countertops. Two ovens are built into white cabinetry, while a flat screen TV is mounted on the blue wall. Natural light comes through large windows, complemented by decorative flowers.

Home in Woodmancote

Premium 4-Bed Cotswolds Escape & Relaxing Retreat

FamilyKitchenPets

4.96 out of 5 average rating, 196 reviews

A warm living room features a plush green sofa adorned with light pink cushions, set against a cheerful yellow wall. A wooden coffee table is placed in the center, topped with a bouquet of pink flowers. Large glass doors offer views of the private garden.

Cottage in Guiting Power

Beautiful Cotswold Cottage with stunning views

Indoor spacesKitchenLayout

Family-friendly home rentals with a pool

Cottage in Stow-on-the-Wold

A charming stone cottage with a steeply pitched roof is framed by lush greenery. The exterior features multiple windows that allow natural light, and a wooden gate leads into a pebbled driveway. The grassy area surrounds the cottage, accentuating its tranquil setting.

Hyde Mill Cottage

FamilyKitchenLong stay

4.97 out of 5 average rating, 100 reviews

4.97 out of 5 average rating, 175 reviews

A large swimming pool is surrounded by a stone patio, featuring four sun loungers and an umbrella for shade. The serene setting includes a wall of greenery and views of the Georgian Manor House in the background, illuminated by bright sunlight.

Home in Bredon

Cotswolds Cottage, Heated Pool, Tithe Barn Views

KitchenFamilyLayout

Condo in Chedworth, Cheltenham

Cosy, rural apartment with breakfast hamper

KitchenIndoor spacesAmenities

4.93 out of 5 average rating, 398 reviews

4.91 out of 5 average rating, 388 reviews

The exterior of a large Regency villa is presented, showcasing its elegant white façade and grand entrance steps. Lush greenery surrounds the building, with trees and well-kept shrubs enhancing the tranquil setting. A private parking area is visible in the foreground.

Apartment in Cheltenham

Stunning flat with swimming pool, garden, parking

FamilyKitchenNearby

Cottage in Somerford Keynes

The cottage's spacious sundeck features an outdoor dining setup with a table and chairs, alongside a charcoal BBQ. French doors lead inside, illuminating the space as the sun sets over the lush greenery. A simple umbrella provides shade, enhancing the outdoor experience.

Cornerstone Cottage a/c LowerMillEstate Cotswolds

FamilyKitchenBathroom

4.93 out of 5 average rating, 146 reviews

Superhost

Cottage in Kemerton

Dovecote Cottage

KitchenIndoor spacesParking

4.86 out of 5 average rating, 127 reviews

4.98 out of 5 average rating, 322 reviews

A tranquil garden scene is displayed, featuring a central pond with a fountain. Surrounding the pond are neatly trimmed hedges and vibrant purple flowers. Lush trees provide shade in the background, contributing to the serene atmosphere of the outdoor space.

Home in Bretforton

Deluxe Coach House at Bretforton Manor with pool

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