Holiday rentals in Winslow

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Top-rated holiday rentals in Winslow

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Top guest favourite
Barn in Buckinghamshire
5.0 out of 5 average rating, 28 reviews

The Fold | A Tucked-Away Retreat, Buckinghamshire

Unwind & have fun at this beautiful tucked-away retreat, on a farm in Buckinghamshire. The Fold is a welcoming annex - part of Barefoot Barn, our family home & self build project designed with Feng Shui. The Fold has its own dedicated garden & patio overlooking the goat paddock & long uninterrupted views of the countryside. It’s designed with a comforting, stylish & peaceful quality, and everything you need for a relaxing & memorable break away with grounding easy walks directly into the farm.

Top guest favourite
A charming cottage exterior is shown, featuring a red-brick façade and a sloped roof. Large windows allow natural light to flood the interior, while a manicured lawn and landscaped greenery surround the home. A stone pathway leads to the entrance, enhancing the inviting scenery.
Guest house in Winslow
4.99 out of 5 average rating, 91 reviews

Cottage Annexe near Addington

A cosy, stylish cottage set within the grounds of Vale Retreats. The perfect spot for an active break with a heated indoor pool*, hot tub and tennis court on site, and direct access to countryside walks and cycles. We’re within trotting distance of Addington Equestrian and perfectly located for Stowe, Silverstone and Bletchley Park. Milton Keynes and Bicester Village are within easy reach. Free parking on drive. EV charger available on request. * Private use of pool and hot tub at agreed times

Superhost
The exterior of a Victorian townhouse is displayed, featuring a mix of brick and white-washed walls under a clear blue sky. The structure showcases multiple windows and a blue door, with a paved path leading to the entryway.
Home in Winslow
4.89 out of 5 average rating, 18 reviews

Victorian Hs in Winslow Conservation Area Sleeps 5

No 14 is a delightful Victorian town house spread over four floors situated, in the conservation area of the ancient market town of Winslow, on Church Street, leading to the church and the town centre. The house was completely refurbished and modernised to the highest specification in the summer of 2020. There are two bedrooms. The upper study can be setup as a further bedroom. One bathroom, a study/office, sitting room, dining room, laundry room, fully equipped kitchen, small private yard.

Top guest favourite
The open kitchen area features dark cabinetry and a modern countertop, complemented by blue pendant lights. A cozy seating area showcases a large smart TV and a soft ottoman. The bedroom highlights a neatly made double bed with plush pillows and a decorative cushion. The kitchen counter is adorned with fresh bread, various jars, and a selection of drinks.
Guest suite in Granborough
4.99 out of 5 average rating, 124 reviews

The Gable - Charming self-contained Annexe

The Gable – A light & airy annex fitted out with love & attention to detail. Bedroom with double-bed with the high-quality mattress, beautiful shower room, comfortable sofa, fully equipped, high-spec kitchen & large smart TV - all comforts to make your stay perfect! Outside you'll have your own private patio. We're in a perfect location to explore Waddesdon Manor, Stowe House, Claydon House, The Chilterns & Bletchley Park, visit Silverstone or grab some retail therapy at Bicester Village

Superhost
The exterior of the barn conversion is depicted, showcasing a traditional black wooden façade. A patio area with a round table and two wooden chairs is visible, accompanied by a large umbrella. Lush greenery and mature trees surround the property, providing a tranquil setting.
Cottage in Granborough
4.99 out of 5 average rating, 119 reviews

Cosy listed barn in peaceful country village.

Beautiful grade 2 listed barn conversion with unique historical features. Mezzanine king bedroom overlooking a large open vaulted ceiling living space. Set in tranquil mature gardens & situated next to the owner's cottage & the historic Saxon village church with a lovely pub serving lunch and evening meals Tues- Sun a 5 minute walk away. We are 30 mins from Bicester Village, Silverstone, Stowe House, Waddesdon Manor, Claydon House, The Ridgeway, The Chilterns, Ascott House & Bletchley Park.

Guest favourite
A clear, inviting swimming pool reflects the blue sky, surrounded by a spacious decking area adorned with colorful flower pots. A shaded seating area is positioned nearby under a pergola, creating a relaxing space for outdoor enjoyment.
Guest house in Drayton Parslow
4.91 out of 5 average rating, 198 reviews

The Pool House, for 2 adults & up to 2 children

The Pool House is a contemporary spacious, private, hideaway, perfect for a romantic getaway or just a stay to explore the surrounding area. Styled with a shabby chic vibe. THE SPACE IS ONLY SUITABLE FOR 2 ADULTS & 2 CHILDREN AGE 12 AND UNDER A HOT TUB SPA AVAILABLE ALL YEAR ROUND. If I have late availability, I will reduce the rate a week before. The pool will close at the end of September 26 THE POOL WILL BE HEATED IN JUNE, JULY & AUGUST, IT WILL NOT BE HEATED IN MAY & SEPTEMBER

Top guest favourite
A spacious sleeping area features a king-size bed with soft linens, complemented by a dresser and decorative vase. Large glass doors provide access to a garden view, allowing natural light to brighten the room. Neutral tones and cozy decor create a relaxing environment.
Guest suite in Mursley
4.96 out of 5 average rating, 141 reviews

Luxurious boutique style self- contained apartment

A stunning boutique style residence that has been brand newly converted and renovated throughout in a stylish decor creating a wonderful cosy atmosphere in a countryside setting ideal for a couple or single person . The property is joined to the main house but has its own entrance at the front. With bedroom with kingsize bed, dining area and comfy armchair, shower room and modern kitchen the apartment overlooks the main house garden and mature trees and can be accessed by double doors .

Top guest favourite
A gravel pathway leads to the entrance of the property, framed by low-maintenance plants and blooming flowers. The rustic brick walls of the building are complemented by wooden accents and trellises, creating a serene outdoor space with pots and greenery along the pathway.
Barn in Adstock
5.0 out of 5 average rating, 78 reviews

The Forge, Adstock/Addington

The Forge is situated within the garden courtyard of the family home. The site was originally part of a stud farm, with the main house belonging to the manager and the Forge accommodated stallions and their mares. The property is independent from the main house with heating supplied from the separate boiler house, comprises a wonderful large beamed double bedroom with en-suite and a fine small kitchen/dining and living area which can accommodate two additional truckle beds on request.

Guest favourite
A path leads to the entrance of the studio apartment, bordered by raised flower and herb beds. The covered patio area features wooden beams and is situated in front of the large glass doors, allowing natural light to illuminate the entrance.
Apartment in Granborough
4.83 out of 5 average rating, 569 reviews

The Herb Garden

A light, airy, ground-floor, single-storey studio apartment. There is a large kitchen and comfortable seating area, and a private patio / garden area. We are well situated for visiting Silverstone, Addington, Oxford, Bicester Village, Waddesdon Manor, Stowe Gardens and Bletchley Park. Also good for working in Milton Keynes or Aylesbury and for trains into London and Birmingham. The apartment has disabled access and ample off-road parking. We are happy to accommodate well-behaved dogs.

Top guest favourite
A well-maintained exterior showcases a charming brick building surrounded by lush greenery. A gravel pathway leads to the entrance, flanked by flower beds and trees, creating a welcoming access point to the property.
Home in Winslow
5.0 out of 5 average rating, 84 reviews

The Barn Studio

The former outbuildings to Winslow’s Tythe barn have been converted to provide stylish and comfortable accommodation. Recently updated, the house is well appointed, with ample space to spread out and relax in the heart of Winslow. We’re located about 20 minutes from Central Milton Keynes and a good base for: - Bicester Village - Bletchley Park - Waddesdon Manor - Stowe Landscape Gardens - MK & Aylesbury Theatre - Xscape Snowdome & Zero Gravity experience - Silverstone circuit

Top guest favourite
A lodge with a semi wrap-around wooden deck is set amidst greenery. Outdoor seating is arranged under a shaded umbrella, while expansive glass doors invite the outdoors in. A clear blue sky complements the tranquil environment.
Cabin in Mursley
4.98 out of 5 average rating, 146 reviews

The Lodge at Burn’s Farm

Relax on your own or with up to 2 children/adults sharing a room at this well appointed 4 seasons made lodge and semi wrap around decking set just outside Mursley village in a picturesque on farm location and 10 minutes via car or accessed from the Redway route to central Milton Keynes by bike or foot. With a selection of farm shops, 2 local public houses and the renowned Horwood House close by and only a 40 minute drive to Silverstone race track, there is plenty to enjoy locally.

Guest favourite
The historic windmill stands majestically against a backdrop of open skies, featuring a stone façade and a brick band near the top. A wooden door leads to the entrance, flanked by a gravel pathway. Lush greenery and fields are visible in the distance, enhancing the rural setting.
Windmill in Oxfordshire
4.97 out of 5 average rating, 233 reviews

The Windmill Blackthorn Hill, Nr. Bicester Village

Featured in the 'Times Newspaper' Top 10 best Places to Stay with Spectacular Views: "A truly amazing experience." Perfect for a romantic escape for 2 or a memorable getaway with family or friends, sleeping up to 4 adults max (+13), with reduced rates for couples wishing to use a single bedroom. If you’d prefer to use both bedrooms, the second bedroom can be prepared for a small additional one-off fee. Bookings for three or four guests automatically include both bedrooms.

Popular amenities for Winslow holiday rentals