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 Knebworth
4.96 out of 5 average rating, 103 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
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, 198 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 exterior of The Cabin showcases a dark wooden structure with large glass doors, surrounded by lush greenery. A small gravel area features potted plants, while a clock adorns the peak of the roof, providing a charming focal point.
Guesthouse in Essex
4.97 out of 5 average rating, 155 reviews

The Cabin Near Stansted Airport

Created to offer a luxurious stay, TheCabin is equipped with a Kingsize bed and luxury bathroom. In the kitchen there is a kettle, toaster, coffee machine, microwave, mini air fryer oven, fridge, induction hob, pots and pans. For breakfast you have eggs, fresh milk, bread, and a variety of cereals, jams and spreads. With beautiful armchairs and a bistro table to eat, work or just sit back to enjoy the smart TV with Netflix, BBC iPlayer, etc. Outside there is a small private garden too.

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, 372 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
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 Essex
4.99 out of 5 average rating, 245 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)

Top Guest favourite
A spacious barn exterior features a hot tub in the foreground, surrounded by lush greenery and blooming flowers. Large glass doors provide views into the interior, while comfortable lounge chairs are positioned on a stone patio for outdoor relaxation.
Farm stay in Thorley
4.99 out of 5 average rating, 186 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
An entrance features a solid wooden door framed by two potted trees, complemented by a textured woven fence. The path leads to a gravel driveway, where a mix of greenery and traditional architecture sets a welcoming tone.
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
A couple relaxes in a bubbling outdoor hot tub, holding glasses, with a scenic view of lush green fields and trees in the background. A champagne bottle sits in an ice bucket beside them, enhancing the tranquil atmosphere.
Shepherd’s hut in Chessington
4.98 out of 5 average rating, 353 reviews

The Ultimate Couples Retreat | 30 Mins from London

This countryside retreat is the perfect romantic escape, just a 35 minute taxi/train ride minutes from London. Unwind in your private luxury hot tub, sip on a complimentary bottle Champagne under the stars, and wake up to breathtaking views of rolling fields and wildlife. Our handcrafted shepherd’s hut blends rustic charm with modern comfort, offering a king-sized stargazing bed, a cozy fire-lit deck, and a luxury bathroom, all set in a peaceful meadow.

Guest favourite
An aerial view showcases the unique geo dome structure surrounded by lush greenery. A wooden deck leads to an outdoor seating area, fire pit, and hot tub. The tranquil setting emphasizes a peaceful retreat in nature.
Dome in West Horsley
4.94 out of 5 average rating, 383 reviews

Unique Dome | Glamping | Hot Tub | Surrey | Adults

Olive Pod is the ultimate cosy, private and picturesque geo dome retreat. Set on a fruit farm in Surrey, in its own secluded field behind tall fir trees, with no other pods or tents nearby. A firm favourite adults-only escape for proposals, anniversaries, birthdays and honeymoons - we can also decorate for your arrival ✨ The perfect place to unwind and recharge in a peaceful natural setting. Ideal for couples or friends. No infants, children or pets.

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, 194 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.

Top Guest favourite
Bungalow in Kent
4.97 out of 5 average rating, 101 reviews

Luxury Spa Retreat: Sauna & Hot Tub

Escape to our exclusive gated spa retreat, nestled on 5.5 acres of serene countryside in picturesque Fawkham, Kent. This private and tranquil haven offers breathtaking views of rolling hills, perfect for relaxation. Unwind in the luxurious sauna, steam room, or hot tub, soaking in the peace after exploring local attractions. Just minutes from Brands Hatch, our retreat blends seclusion with convenience, your ultimate quiet getaway awaits.

Popular amenities for Upshire holiday rentals

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