
Vacation rentals in Chestnut Street
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Top-rated vacation rentals in Chestnut Street
Guests agree: these stays are highly rated for location, cleanliness, and more.

Self-contained annex, with off-road parking.
Self-contained annex in Sittingbourne, perfect if you are visiting the area for work or leisure. Everything you need for a comfortable stay in your own completely private place, with driveway parking and fast WiFi. The accommodation comprises a bedroom /lounge /working room, kitchen and bathroom. The annex, especially the bedroom, is very quiet and peaceful. Located conveniently for the motorway and also easy access to the town centre, train station, shops, takeaways, restaurants and pubs.

The Oaks. Beautiful Scandi style cabin on stilts
The Oaks cabin, a romantic escape from daily life - tranquil and luxurious. Relax from the moment you arrive. Nestled next to ancient woodland within a family small holding. Adjoining the High Weald National Landscape, 2 miles from Tenterden in the Kent countryside. From here you can enjoy wonderful experiences in Kent and Sussex and end your day in one of the great local pubs, breweries or vineyards. Immerse yourself in nature from the deck and adjoining field. A cabin of pure, sleek escapism.

Grand Bubble
Grand bubble sleeps 4 people who can enjoy the ultimate view of nature. You can fall asleep with the stars and wake up to the rising sun. This bubble has the wow factor and includes your own hot tub, BBQ, a shower, a flushing toilet, outdoor chess set and a golf buggy. The bubble is very secluded set at a bottom of a 12 acre field off a woodland. Out side of the bubble is a very large outdoor gazebo with comfy seating and a large gas bbq so even if it rains you can still bbq comfortably.

Romantic Hideaway & Hot tub in Kent Countryside.
A White Romantic Garden Cottage & Luxury Hot Tub set in the heart of the Kent Countryside with idyllic views across our orchards . Disconnect with the world, relaxing in the Hot Tub, tucked away in the Private woodland setting surrounded by twinkling fairy lights under the starry sky. The Cottage has been designed to provide comfort, space & tranquillity with its vaulted ceilings & private gardens & summerhouse & parking. Pubs are within walking distance & a nearby Forest to explore .

Elegant Cosy Hideaway (The Clarence)
Extremely private hut set within 15 acres of wilderness to relax in the remotest part of Kent with direct access into the beautiful valley. Most guests visit us to shut the world out. However, we are also spoilt for things to do locally and have some terrific pubs/ restaurants. “We loved hearing the owl sending us to sleep” “this was without doubt the best place I've ever stayed! It was private, clean, warm, cosy..for the price paid it was a complete bargain" - Nicole, November 2024

Unique Self contained lodge within stable setting
This unique stylish property is very close to junction 5 on the M2 with easy access to London. Plan your visits to Canterbury Cathedral, Leeds Castle, Whitstable, Rochester Castle and many other tourist attractions with ease from this central location. The Property is two miles from the closest shop and the nearest train station is Sittingbourne. The property is set amongst beautiful paddocks with horses in livery in the adjacent stables. There is ample secure parking and easy access.

Stable Conversion
🌿 Private Hot Tub | Netflix | Free WiFi & Parking Relax in this beautifully converted stable, perfect for a peaceful escape. Enjoy a sliding glass door enclosed, completely private hot tub, ideal in all weather. Unwind indoors with a TV including Netflix and YouTube Premium. The space offers free WiFi and free on-site parking, making it ideal for both leisure and remote working. Cosy, comfortable and thoughtfully converted, it’s an ideal base for a romantic break or quiet getaway.

Cosy Countryside Annex
Cosy countryside annex in rural Kent, perfect for a peaceful getaway or a convenient stopover. Located on the driveway opposite our home, The Little House offers its own living space in a peaceful countryside setting. Base price is for one guest; additional guests are welcome for a small nightly supplement NOTICE: A neighbouring farm is currently carrying out building works. There may be some noise during normal working hours (Mon–Fri, but evenings and weekends are generally quiet.

Acorn Lodge @ The Oaks Retreat
This memorable place is anything but ordinary. It is The Oaks Retreat, WINNER of the Paris Design awards 2024 'best hospitality interior', an architecturally inspired bespoke woodland Airbnb located in the seaside town of Whitstable. The Acorn Lodge is a bespoke 1 king size bedroom retreat fully customized with high-end finishes. It must be seen in person to be fully appreciated. Our Wellness area is equipped with a log sauna, a cold plunge and outdoor shower.

Lake House Staycation
Escape to The Lakehouse, a charming lakeside retreat steeped in history. Once a working quarry, the lake provided the very stone used to build this beautiful home—and even nearby Leeds Castle. Lovingly restored with original stonework, this tranquil hideaway offers stunning water views, modern comforts, and timeless character. Enjoy peaceful walks, local pubs, and the rolling Kent countryside—perfect for a romantic getaway or serene weekend escape.

Home Away From Home | FREE Parking | EV Charger
Welcome to your perfect getaway! This charming apartment offers the best of both worlds: modern comforts in a vibrant setting. Located in the heart of Sittingbourne, you will be just steps away from all top attractions, cafes, the high street, restaurants and the train station . Whether you are here for business or pleasure, this apartment provides the ideal base to explore and unwind. Book now and experience Sittingbourne like locals.

Cosy 3 bedroom cottage in the heart of Kent
Shillinghurst Cottage is the perfect getaway for a relaxing break for friends, couples or a family break. It is cosy, comfortable yet modern and comes with everything you would expect to make it the ideal home away from home. Set in the heart of the beautiful village of Borden, it will suit individuals who like country walks, relaxing in a peaceful surrounding or exploring the many towns and cities nearby.
Popular amenities for Chestnut Street vacation rentals
Other great vacation rentals in Chestnut Street

Victorian gardener's lodge set in Kent countryside

Secluded Rural Bungalow | All Ground Floor Home

The Bishop's Den

Contractor & Corporate Stay & 4 free car park

Lush 2 Bed Home I Free Parking I Near Chatham Dock

Cherry Blossom shepherdsHut

High Trees Lodge – Luxury Retreat • 2 King Suites

Little Orchard Holiday Rental
Destinations to explore
- Wembley Stadium
- Covent Garden
- Kings Cross
- Paddington
- Hampstead Heath
- St Pancras International
- London Bridge
- ExCeL London
- The O2
- Emirates Stadium
- Tower Bridge
- Clapham Common
- Buckingham Palace
- Alexandra Palace
- Chessington World of Adventures Resort
- Big Ben
- London Stadium
- Victoria Park
- Primrose Hill
- British Museum
- London Eye
- St Paul's Cathedral
- Trafalgar Square
- Hampton Court Palace





