Holiday houses in Greenstead Green

Rupert’s Cottage, Coggeshall

Escape to the charming market town of Coggeshall and enjoy a stay at Rupert’s Cottage, our beautifully presented, stylishly furnished home-from-home that comfortably sleeps up to four guests. Located just steps away from Rupert’s Taproom and Cocktail Bar, you’ll be perfectly placed to experience an enjoyable evening right on your doorstep. You’ll also be within walking distance of some great local restaurants, independent shops, and the town’s historic sites, all adding to the charm of your stay

Location · Family · Bathroom

Woodpeckers Annexe in Gosfield

Lovely self contained annexe in the village of Gosfield, close proximity to Halstead. The location is ideal for visiting places like Sudbury, Finchingfield, Lavenham & many more beautiful Essex/ Suffolk villages. ideal if attending Gosfield Hall or other wedding venues in the local area. The property is on two floors with the bedroom & shower room upstairs. The kitchen has a sink, fridge, double hob, microwave and breakfast bar. The Lounge area has a settee & television. Full central heating.

Family · Location · Indoor spaces

The Bakehouse, Coggeshall

Welcome to The Bakehouse. A light-filled, cottage tucked away in our garden, right in the heart of historic Coggeshall. Once a working bakehouse, this one-bedroom retreat blends the character of the old with the ease of the new. Whether you're here for a quiet solo stay, a romantic weekend, or travelling to visit family, there's space to slow down & settle in. Step outside & you’re moments from historic sites, leafy green spaces & charming shops, each with stories woven through the centuries.

Value · Family · Heating

Historic charm, modern comfort.

Recently renovated to the highest standard, The Loft is a spacious and immaculately presented two-bedroom flat in the heart of Castle Hedingham. Set within a centuries-old building, it perfectly blends historic character with contemporary style, offering all the modern amenities you need for a comfortable and relaxing stay. Whether you're visiting for a weekend escape or a longer break, The Loft provides the ideal base to explore this beautiful, historic village and surrounding countryside.

Location · Value · Bathroom

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!

Value · Family · Decor

Recently converted Nissen Barn on beautiful farm

The recently converted Nissen Barn is located on a farm in its own private meadow. The barn is surrounded by the beautiful Essex countryside - rolling hills, ancient trees, wildflowers and grasses, hedgerows, horses and sheep. The conversion was completed in March 2021 and sleeps 4 adults in 2 big bedrooms. There is also a loft bedroom accessed by a hidden door with a king size mattress suitable for older children or a couple. Perfect for families, but note there is no enclosed garden.

Location · Value · View

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)

Value · Family · Sleep quality

Bedrock- A Real Flintstone Style Cave Experience

A hand-crafted cave home inspired by The Flintstones. One of the most unique stays in the UK. Carved concrete walls, curved ceilings, cave-style beds. A destination in itself! 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.

Value · Location · Cleanliness

The Dell - Country Holiday Let

The Dell sleeps up four guests and is located in the small village of White Colne, only 15 minutes away from the oldest recorded town in the UK, Colchester. On the Essex-Suffolk border you have a great base to explore East Anglia’s towns and attractions. This is a private annex building set in the grounds of our family home. To note we do have dogs who roam freely in our gardens. Should you have any questions at all about The Dell please do not hesitate in messaging us :) Jaine

Location · Family · Heating

Luxury cottage in the centre of Lavenham

This beautifully restored period cottage offers luxury boutique accommodation, is centrally located within the village and within easy walking distance to numerous pubs, eateries and specialty shops. Lavenham is considered to be England's most well-preserved medieval town. With its winding streets, timber-framed buildings and quaint cottages, it is also Suffolk's prettiest wool town and is ideally located to explore the beautiful Suffolk countryside.

Location · Value · Indoor spaces

Exquisite 1-bedroom apartment with on-site parking

Tucked away in a tranquil spot, this cosy apartment offers the perfect escape to relax, refresh and recharge. Enjoy stunning lake views, the soothing sound of a water fountain, and wake up to quacking ducks, you may even spot a muntjac! Though it feels like the countryside, it’s just a stone’s throw from the town centre and all amenities. This centrally located gem is not to be missed—we guarantee you’ll be back for more!

Family · Location · Amenities

Peaceful Retreat; Courtyard, Pub & Country Walks

Tolleridges Guest House is a private, dog-friendly retreat in the peaceful village of Colne Engaine. Ideal for couples, small families, wedding guests and work trips, it sleeps up to 4 with one double bedroom and a sofa bed. Modern kitchenette, shower room, cosy lounge and enclosed private courtyard. Country pub and countryside walks nearby. Unload at the gate, with free village parking a short walk away.

Family · Location · Access