Holiday houses in Upshire

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Top-rated holiday rentals in Upshire

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Guest favourite
Cottage in Ongar
4.88 out of 5 average rating, 372 reviews

Willowbank Cottage, Sleeps 4, peaceful location

Willowbank Cottage is a lovely, bright 3 bedroom cottage in a beautiful, quiet location, surrounded by Essex countryside. You will have the entire place to yourselves with private entrance and courtyard garden. Free off street parking for 2 cars. The perfect, peaceful countryside location to unwind and relax, yet Harlow & Epping towns are just a short drive. Nearest train stations are Epping, Harlow Town, Harlow Mill, 15 mins by car. Stansted Airport is 20 mins by car. NAPA centre 15 mins.

Guest favourite
A charming thatched cottage is set within a well-maintained garden, featuring a gravel driveway lined with greenery. The building's unique architecture is complemented by large windows, providing a welcoming appearance in a serene outdoor environment.
Cottage in Barley
4.96 out of 5 average rating, 305 reviews

Beautiful thatched cottage, Barley, Herts

Ravello Rose is a Grade ll Listed thatched cottage in the historic village of Barley, ideal for walking or cycling and close to Cambridge and Duxford IWM. Situated in a peaceful lane ten minutes walk from the village centre and 2 pubs, the property has its own front door, well equipped kitchenette, modern shower and toilet, large lounge diner, inglenook and two double bedrooms. Free parking for one car on our drive. An EV charger can be used for overnight charging. Ask about availability/cost.

Top Guest favourite
The exterior of a converted barn is shown, featuring a rustic design with dark wooden siding and a charming red roof. A gravel driveway leads to a fenced area with plants, while a tree and shrubs decorate the surrounding landscape under a clear blue sky.
Barn in Thundridge
4.99 out of 5 average rating, 175 reviews

The Byre at Cold Christmas

Escape to the country and stay in a cosy converted barn with a log burning stove and a secluded sunny patio area with outdoor dining and barbeque. Positioned in the beautiful countryside near Ware town, Cold Christmas has an abundance of lovely walks and is conveniently situated close to Hanbury Manor and Fanhams Hall, both of which offer a variety of amenities including a golf course, health spa and fine dining. Maltons, one of the area's finest restaurants is just at the end of the lane.

Top Guest favourite
A 1960s Brutalist water tower stands tall against a clear blue sky, showcasing its distinctive conical shape. The concrete structure is surrounded by lush greenery and farmland, allowing for unobstructed views of the expansive countryside.
Home in Tonwell
4.97 out of 5 average rating, 39 reviews

Tonwell Water Tower

Only a short hop from London, yet surrounded by beautiful and seemingly endless countryside, Tonwell Tower is a spectacular getaway any time of year. The newly converted 1964 Brutalist water tower is six stories, four bedrooms, four bathrooms, and eight friends & family of magic. Cosy nights, romantic dinners, walks, cycling, fresh air and some super pubs, historic houses, golf, museums, fishing, spas, zorbing & more. Come. It is beautiful, thrilling, peaceful and stunning - all at once.

Guest favourite
A bright and airy sunroom features a comfortable sitting area with patterned seating and yellow cushions. Large windows allow natural light to fill the space, while a modern kitchen is visible in the background, creating an inviting environment for relaxation.
Home in Essex
4.94 out of 5 average rating, 16 reviews

Modern townhouse with easy access to London

Charming 3-bedroom townhouse in the heart of Ingatestone village, just a 5-min walk to the train station with a direct 20-min ride to London. Ideal for families, business travelers, or visitors to London, the house is surrounded by scenic countryside walks and within walking distance of pubs, restaurants, and independent shops. Fully equipped kitchen, cosy living room, patio and balcony. High-speed Wi-Fi, smart TV, and free off street parking. Perfect blend of village charm and city access.

Top Guest favourite
A window offers a view of the neighborhood, showcasing residential homes and a glimpse of greenery. Bright skies with scattered clouds provide a natural light to the airy space, while the window’s stylish blinds are partially closed.
Home in Greater London
4.98 out of 5 average rating, 184 reviews

3 bedroom new home 7mins from Tottenham Stadium

This modern and comfortable three-bedroom house is perfect for families and groups seeking a leisurely stay, commonly praised by guests as a home away from home. The property features three double bedrooms, two with king-sized beds and one with two single beds. Additionally, there is one bathroom and one toilet, an ideal arrangement for families and larger groups! The Tottenham Hotspur Stadium is a 7 minute walk from the property, and White Hart Lane overground station is a 13 minute walk.

Top Guest favourite
Apartment in Greater London
5 out of 5 average rating, 9 reviews

Stylishly Curated Boutique Retreat Calm & Comfort

A newly renovated, design-led space with a boutique hotel feel. Thoughtfully curated interiors, a fully equipped kitchen and a dedicated workspace create a stylish yet functional stay. Sink into Egyptian cotton linens and enjoy the quiet, calming atmosphere. Every detail has been crafted for comfort and aesthetic pleasure, ideal for guests who value calm, curated design and subtle luxury in a peaceful retreat made to feel like your own private hideaway. - On the Underground's Central Line

Top Guest favourite
An elegantly designed bedroom features a spacious super king bed adorned with soft linens and stacked towels. A freestanding bath is positioned nearby, complemented by wooden wall accents. A cozy robe hangs in the background, while soft lighting contributes to a serene atmosphere.
Farm stay in Essex
4.98 out of 5 average rating, 361 reviews

Exclusive retreat on a private lake

Enjoy a truly unique stay in this exclusive lodge. Situated on its own private lake, you will have everything you need to enjoy a blissful retreat with award winning country pubs such as The Dog & Pickle only a walk away. Please note: 1. We are strictly a minimum of two night stays. 2. We can only accept infants under 6 months old. 3. There is no swimming or paddle boarding allowed in the lake. NEW FOR 2026 - The Wellness Deck Sauna, Cold Plunge & outdoor shower, ready for use now!

Guest favourite
A private outdoor seating area features a round table surrounded by four chairs. A comfortable sectional sofa is positioned nearby, providing a space for relaxation. The backdrop is composed of a textured brick wall and a fenced garden area, creating a sense of seclusion.
Tiny home in Loughton
4.91 out of 5 average rating, 78 reviews

Studio 17 - New Large Studio with Parking

Brand new large studio apartment finished to a very high standard at the rear of our garden with a fully functional Kitchen,Bathroom and with a spacious bedroom / living space with a dedicated workspace and outdoor furniture. We are located in the lovely town of Loughton, walking distance to Epping Forrest and 30-35 minute drive to Stansted Airport and 1.5 Mile to Loughton Station. Free parking on the front drive, complimentary WI-FI, 65” Smart TV, Bluetooth Sound System Speakers.

Top Guest favourite
A long, polished dining table is set with silver cloches and elegant glassware, positioned beneath a large window. The expansive view reveals lush vineyard rows and greenery framed by soft, natural light. Potted plants add a touch of color to the scene.
Villa in Toppesfield
4.99 out of 5 average rating, 238 reviews

Luxury, contemporary vineyard property - 2 adults

Toppesfield Wine Centre is a contemporary ‘Scandi-style villa’ with a large open plan lounge/dining area which has a giant picture window overlooking Toppesfield Vineyard and full height glass sliding doors looking out onto a beautiful garden/ private patio with a large outside dining table and a luxurious day bed. It has a luxury bedroom with superking bed, view over the vineyard, luxury bathroom, tennis court and 4 person jacuzzi (2nd bedroom available via Airbnb 4 person listing)

Guest favourite
Condo in Waltham Abbey
5 out of 5 average rating, 36 reviews

Beautiful Peaceful Studio Flat in Waltham Abbey

A spacious and bright one bedroom studio apartment located in Waltham Abbey. This property benefits from a large living room, kitchen, bedroom, bathroom and free parking. The local supermarket is a couple of minutes walk away and just a short walk to the historic market town centre of Waltham Abbey with a lovely array of shops and Lee Valley Country Park. A 5 minute drive to Junction 26 of the M25 or a 10 minute drive takes you to Waltham Cross Station (traffic dependant).

Guest favourite
Apartment in Snaresbrook
5 out of 5 average rating, 55 reviews

Wanstead Luxe Hideaway - Luxury 2 Bedroom

Beautiful 2 bedroom apartment. Georgian conversion building once owned by Charles Dickens. Pet & child friendly, with private garden terrace. Underfloor heating throughout, 1 min walk to the high street & local amenities. 5 min walk to two central line stations. Off street allocated parking, great for driving in/out of London. Open plan, fully integrated kitchen, all appliances & excellent amenities, superfast Wi-Fi. Smart TV's with Sky TV throughout & Smart TV in bathroom.

Popular amenities for Upshire holiday rentals

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  4. Essex
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