Vacation rentals with a pool in Hertfordshire

Retreat by the Mill-perfect for a relaxing getaway

Kick back and relax in this stylish rural property which is situated in the garden of our HERTFORDSHIRE home & next to a grade II* listed windmill. It is suitable for both holiday and business stays. Free parking (3 cars max). Perfect for exploring the local Hertfordshire countryside or heading into London or Cambridge–both within easy reach. Both floors have a living area with double sofa bed & kitchen/diner, double bedroom and shower room. Electric car charging available. This is NOT Norfolk!

Location · Family · Pets

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

Location · Value · Condition

Luxury 5-Bed Retreat | Private Pool & Free Parking

Discover a luxurious retreat in Luton! This spacious 5-bedroom house, managed by Jesswood Properties, is perfect for business travellers, corporate teams, and family gatherings . Enjoy a private garden, seasonal swimming pool open from May through to September , and spacious bedrooms. Set in a quiet residential area, the property offers generous space, multiple bathrooms, fast WiFi, and private parking — making it ideal for short stays, long-term projects, relocations, and extended bookings.

Layout · Check-in · Pool

Farm stay in Buckinghamshire

Come and relax in our beautiful farm cottage with a private deck and garden surrounded by amazing rolling countryside. Perfect for spending some special time with your family. You can also book to take a dip in our heated indoor swimming pool which is perfect for all ages. We are a great central spot for visits to London and Oxford and have some lovely attractions within 20mins of us including Waddesdon Manor, Bletchley Park and Whipsnade Zoo. *Outside Sauna and copper bath coming Jan 2025*

Value · Family · Layout

Hitchin Barn conversion

Set in beautiful Hertfordshire countryside, yet only minutes away from Hitchin Town Centre and Luton Airport we offer a relaxed and peaceful stay in our detached 17th century tithe barn. Four bedrooms, (a twin and three doubles) one double is ensuite, one family bathroom, two shower rooms and a separate toilet, indoor private pool, games room with full sized snooker table, large kitchen/diner and galleried lounge overlooking pool. N.B there is also a sofa bed and three fold up guest beds.

Family · Location · Heating

The Piggery - Country Getaway

Enjoy a unique stay in a picturesque rural setting, The Piggery is the perfect getaway for those looking for rest and relaxation. Located between Cambridge & London, it is ideally situated for country walks and pursuits. Set in the 12 acre grounds of the manor house, once the family home and filming location for Britain's most famous TV chef, guests will have access to the gardens, outdoor pizza ovens, tennis court, swimming pool and fresh produce from the walled kitchen gardens.

Location · Family · Decor

Riverside Traditional Log Cabin

🏊‍♂️✨ OUTDOOR SWIMMING POOL IS OPEN ✨🏊‍♀️🌞 ENJOY YOUR SWIM & STAYS Nestled by the river, our rustic yet modern cabin offers stunning scenery in every direction. Wake up to scenic surroundings and peaceful views that instantly slow you down. Thoughtfully designed for comfort, the cabin blends cozy charm with modern touches so you can truly relax. We love creating more than just a stay—we want every guest to enjoy a comfortable, memorable escape and a true experience in nature.

Location · Outdoor spaces · River

Luxury Retreat | Private Heated Pool & Hot Tub

Welcome to The Pool House—a beautifully designed 1,000 sq. ft luxury countryside annex in the heart of Bedfordshire. Created for relaxation, escape and a touch of indulgence, this stylish two-bedroom, two-bathroom retreat features a private garden with an exclusive heated plunge pool. Elevate your stay with optional wellness extras including massages, facials, reflexology and private sound baths. Advance booking required. Simply arrive, unwind and enjoy a countryside escape.

Location · Family · Accuracy

Luxury 5BR | Pool & Games Room

Luxury 5-bedroom retreat in central Harlow, perfect for families, groups and contractor stays. Enjoy a heated swimming pool reaching 22 Celsius, games room with professional pool table, large private garden with seating, and off-street parking. Features a fully equipped kitchen with coffee machine, Netflix, and luxury essentials. Close to Harlow Town Centre, retail parks, Princess Alexandra Hospital, business parks, direct London train links and Stansted Airport.

Location · Family · Check-in

Glorious Gardens

Come and have fun with the whole family at this very special place. Heaven for children and adults alike with endless activities; trampoline, swimming pool, football, table tennis, swings, fire pit, pick home grown tomatoes, gorgeous patio, 3 acres of parkland garden to explore and an amazing tree house! 5 Bedrooms and lots of space for an extended family stay. 25 minutes train to London from Beaconsfield. 30 minutes drive from Heathrow airport.

Family · Location · Pets

Romantic Vineyard Hut on Organic Farm

Whether you're after some time out, a romantic hideaway, a place to write a book, do some yoga, take part in a wine tour, cycle the Chilterns or just sit back and gaze at the stars; Wildflower shepherds hut is a perfect retreat for up to 2 people to restore and reconnect in nature. Warm, inviting and luxurious, our shepherd’s hut is situated in our organic vineyard run by Woodfine Wine amongst the wildflowers and all that nature has to offer.

Family · Location · View

3-Bed Cottage | Indoor Pool Access | Sleeps 6

Cosy 3-bed cottage set within private gated grounds in Harlow, offering a comfortable stay for families, small groups or contractors working in the area. The cottage sleeps up to 6 guests and provides access to a large indoor heated swimming pool on the estate. Conveniently located near the M11 and London Stansted Airport, the property offers a quiet setting while still being close to local amenities and transport links.

Location · Value · Getting around