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Holiday houses in Upshire

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Upshire

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Cabin in Roydon
4.99 out of 5 average rating, 134 reviews

Secret Hideout Jacuzzi•Valley Views•Firepit•bbq

Tucked away in nature, The Hideout Retreat is a peaceful, spiritual escape where you can reconnect, breathe deeply, and truly unwind in nature. Wake to panoramic valley views, let silence ground you, and end the night watching the stars in complete tranquillity. A secret refuge for rest, clarity, and calm. • Stunning valley views • Outdoor jacuzzi + sunset soaks • Fire pit for cosy nights • BBQ for outdoor dining • Morning coffee on the deck Enjoy the perfect stay in nature and true peace.

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, 223 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
Barn in Wareside
5.0 out of 5 average rating, 13 reviews

Glorious countryside barn: a dream staycation

Our exquisite green oak framed barn is accessed via a private farm track and sits amid open farmland and woodland, right on the Hertfordshire Way. Set behind electric gates, within the grounds of our home. The barn is oak throughout and feels like a Swiss ski lodge in the countryside giving a dream holiday feel. The open-plan layout seamlessly connects the living, dining, kitchen and terrace, creating a spacious and versatile living experience. Natural light floods through the windows.

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, 386 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
4.92 out of 5 average rating, 88 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 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, 193 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
Condo in Waltham Abbey
5.0 out of 5 average rating, 40 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).

Top Guest favourite
Cave in Hertfordshire
5.0 out of 5 average rating, 31 reviews

Bedrock – A Flintstone-Inspired Cave Stay

Not your average Airbnb... Step back in time and experience Bedrock, a truly one-of-a-kind Flintstone-inspired cave retreat where Stone Age charm meets modern comfort. Designed to comfortably accommodate 2 adults and 2 children, Bedrock offers a warm, cozy, and thoughtfully crafted interior: * Soft warm lighting to enhance the cave-like ambiance * A snug yet functional space that blends prehistoric style with modern convenience * Just minutes away from Hertfordshire Zoo.

Top Guest favourite
Cabin in Theydon Mount
5.0 out of 5 average rating, 46 reviews

Chestnut Tree Barn

Kick back and relax in this calm, stylish space. Nestled in the Essex countryside with easy access to London, this charming property offers the best of both worlds. Beautiful walks, where you can spot deer and other wildlife, bird watching, cycling; fabulous local country pubs and a peaceful base from which to explore the sights of London . The market town of Epping with its weekly market, tube station, shops and restaurants is five minute drive away.

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, 139 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 Goffs Oak
4.93 out of 5 average rating, 222 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
Tiny home in Loughton
4.85 out of 5 average rating, 280 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.

Popular amenities for Upshire holiday rentals