Holiday houses in Upshire

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Top-rated holiday rentals in Upshire

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Guest favourite
The exterior of the architect-designed home is showcased during twilight, with large glass panels reflecting warm light. A spacious patio area is visible, furnished with a dining table and chairs. Green grass surrounds the home, enhancing the inviting atmosphere of the outdoor space.
Barn in Old Knebworth
4.96 out of 5 average rating, 105 reviews

Stunning Oak Glass House London Train Hot Tub

This luxurious, architect-designed 3,400 sqft home offers a rare opportunity for elegant living in a recently rebuilt, renovated 4-bed, 4-bathroom house. Set on a large plot, the house features multiple oak-and-glass facades and includes a charming Victorian-era cottage. The gated property presents the ultimate in open-plan living with sustainable green oak construction, light-filled spaces, expansive hallways, and grand direct glazed entrances. Trampoline/ BBQ / Football/ Hot Tub package

Top Guest favourite
Barn in Thundridge
5 out of 5 average rating, 204 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
The lodge's exterior is highlighted at dusk, featuring a curved wooden structure with large windows glowing warmly. A deck with outdoor seating invites relaxation, surrounded by gravel and lush greenery, showcasing the peaceful ambiance of the countryside.
Farm stay in Essex
4.98 out of 5 average rating, 376 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!

Top Guest favourite
The open-concept kitchen and living area features exposed wooden beams and a modern design. A spacious kitchen island is equipped with kitchenware and coffee-making equipment. A comfortable seating area with light-colored sofas is visible, complemented by decorative art and natural light from large windows.
Farm stay in Thorley
4.99 out of 5 average rating, 187 reviews

3 Bedroom Barn Conversion Nr Stansted +hot tub

Escape to the beautiful English countryside with a group of friends or family to this stunning barn conversion on the edge of Bishops Stortford. With it's exposed oak beams, log fireplace and hot tub, this is a special place to relax in comfort and unwind, a perfect escape from the city. We aim to provide a luxurious stay in this 3 bedroom barn conversion which can sleep up to 6 people. All three bedrooms have ensuite bathrooms and we use B-Corp bedding, shampoos & conditioners.

Guest favourite
Barn in Nr Epping
4.97 out of 5 average rating, 184 reviews

Escape to the Country with easy reach of the Tube.

Tawney Lodge is beautifully decorated countryside retreat with a kitchen, wet room, relaxing sitting room and huge bedroom with a king size bed. All rooms overlooking stunning countryside. We back onto Ongar Park Woods which joins to Epping Forest making a wonderful walk into Epping. It is located 2 miles from Epping and ideally located for people attending weddings at Gaynes Park, Blake Hall and Mulberry House. Epping tube station (central line) is under five minutes drive.

Guest favourite
Cottage in Moreton
4.95 out of 5 average rating, 527 reviews

The Barn, beautiful rural retreat

The Barn is located within the grounds of our Grade 2 listed Cottage and yet is far enough away from the main house to allow our guests privacy. The property offers two luxurious double bedrooms and a modern bathroom with shower and bath. The light and spacious living / kitchen area is fully equipped with all appliances including a dishwasher and provides comfortable seating for all our guests. Guests will receive a welcome pack of goodies on arrival.

Top Guest favourite
The exterior of the annex features large glass doors that open to a wooden deck. A small seating area with a table is visible on the patio, surrounded by greenery. Inside, a welcoming living space can be seen, illuminated by natural light.
Guesthouse in Essex
4.94 out of 5 average rating, 126 reviews

The Annex

Escape to our modern, self-contained annex bordering Epping Forest. Perfect for hikers & wedding guests or those just looking for a peaceful retreat • Plush King bed, dedicated desk, Sky TV, and high-speed Wi-Fi. • 12m walk to High St; 20m walk to Epping Station (Central Line to London). • Kitchenette: Fridge, microwave, kettle, and toaster. • Private access and on-site parking. Experience woodland peace with easy city access. Book your stay!

Guest favourite
An outdoor seating area is shaded by a wooden pergola, featuring a comfortable sectional sofa and a coffee table. A hot tub, surrounded by stone tiles, adds a relaxed ambiance. Warm lighting is provided by string lights overhead, enhancing the cozy outdoor setting.
Barn in Goff's Oak
4.93 out of 5 average rating, 197 reviews

Grouse Lodge Private Gated Cosy Barn with Hot Tub

Grouse lodge is a stunning barn conversion located on a gated and private residency in Hertfordshire. Being just a stones throw away from London, you get to enjoy the best of both at ease. With its rural location, and breathtaking surroundings, it is a perfect place to retreat away from all the hustle and bustle. The interior has been designed to match, with its warm, cosy and sophisticated style, giving you the full rural retreat experience.

Guest favourite
A charming garden apartment is showcased with a well-maintained lawn. Grass extends toward the structure, which features large glass doors leading into the living area. Surrounding greenery enhances the peaceful setting, while a patio area with seating is visible in front of the apartment.
Guesthouse in Essex
4.91 out of 5 average rating, 161 reviews

🌳 The Garden Apartment 🌳

Tucked away in corner of Epping Forest is our quiet and luxurious garden apartment, ready to welcome you for your stay. Complemented with live house plants the apartment comprises, a fully equipped kitchen offering the ability for cooking fresh local food. In the summer enjoy your own private garden or enjoy the warm comfort of the open plan living space. Just a 10 min walk from our nearest London station and high street and supermarket.

Guest favourite
Tiny home in Essex
4.84 out of 5 average rating, 276 reviews

Modern self contained tiny home with patio

Self contained modern annexe with private patio and own entrance near central line tube station in a very calm green area near epping forest. Easy commute to central London or 30min car drive to Stansted airport, great location to explore London and come back to relax in the evening. Epping forest and Roding Valley Meadows nearby for a nice walk. Loughton high street restaurants and boutique shops just within short walk.

Top Guest favourite
A welcoming lounge area showcases a fireplace with a warm glow, framed by a brick surround. A spacious seating arrangement lies near a soft area rug with intricate patterns. A wooden bookshelf filled with various books stands nearby, inviting guests to relax and enjoy the space.
Windmill in Aythorpe Roding
4.99 out of 5 average rating, 299 reviews

Rodings Millhouse and Windmill

As you arrive, you’ll be greeted by the charming and historic Aythorpe Roding Windmill, nestled in the peaceful Essex countryside. Set on over 2 acres of private gardens and surrounded by open fields and working farms, it offers a truly unique and tranquil escape. Whether you’re exploring the grounds or relaxing in the serene setting, it’s a place to unwind and reconnect with nature.

Guest favourite
A charming black-clad cottage is softly illuminated by string lights, set against a dusk sky. A picnic table with floral centerpieces occupies the outdoor space, surrounded by a wooden fence. Warm light glows from the cottage windows, creating an inviting atmosphere.
Place to stay in Chorleywood
4.92 out of 5 average rating, 218 reviews

Romantic Cabin w/ Hot Tub & Fire Pit

Escape to this luxury countryside retreat, perfect for couples or families, just 40 minutes from Central London. Sleeping up to four guests, this private farm hideaway blends comfort and style with peaceful surroundings. relax in your own hot tub under the stars, cosy up by the fire pit, or enjoy a slow morning in the roll-top bath - the perfect setting to unwind and reconnect.

Popular amenities for Upshire holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Essex
  5. Upshire