Vacation rentals in Chestnut Street

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Top-rated vacation rentals in Chestnut Street

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Top guest favorite
The exterior of the annex is showcased, featuring vertical wooden slats and a glass-paneled door. A small window is visible, allowing natural light into the space. The entrance is set on a paved path, surrounded by greenery and a water storage tank nearby.
Guesthouse in Sittingbourne
4.93 out of 5 average rating, 303 reviews

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.

Guest favorite
A modern dining area features a round table set with plates and flowers, surrounded by four black chairs. A cozy sofa is positioned nearby, with a soft color palette complementing the overall design. Light enters through an opening to the kitchen area.
Home in Rainham
4.96 out of 5 average rating, 157 reviews

Modern 2 Bed House in Rainham, Kent

Welcome to this modern home from home in Rainham, Kent. Perfect for any stay - leisure, work, visiting family/friends & local attractions. Conveniently situated close to local amenities, 5-minute walk to train station and town centre, restaurants, pubs, bars, shops & much more. Including 2 spacious bedrooms with double & king size bed, new luxury bathroom & open lounge with all Virgin TV channels, fast WiFi, fully equipped modern kitchen, large garden & a private parking space for your stay.

Guest favorite
A modern kitchen is equipped with light grey cabinets and wooden countertops. A gas stove and microwave are positioned on the left, while a sink and washing machine are located on the right. Natural light enters through a window covered by delicate blinds.
Apartment in Kent
4.92 out of 5 average rating, 24 reviews

First floor flat with 2 dbl bedrooms + Fast Wi-Fi

Comfortable first floor flat, located 1km west of the town centre and station. Dedicated entrance door with stairs leading up to the flat which has 2 bedrooms, lounge diner, kitchen and bathroom. The master bedroom can be made up with twin beds or a large double bed. The 2nd bedroom has a double bed. Small private garden at the rear with patio table and chairs. On-street parking available along Bassett Road or College Road nearby. Please note that we are unable to accept pets at this property.

Superhost
Home in Kent
5.0 out of 5 average rating, 6 reviews

2 Bed Home | Central location | Kent | Contractors

Fully equipped 2 bedroom home ideal for contractors, long-term stays, professionals commuting to London or those relocating to Kent. Key Features: - Laundry facilities - Parking for 2 vehicles + EV charging - Bicycle Storage - Trains to London St Pancras International = 50mins. Local Area -Sittingbourne Railway Station - 10 mins walk - Sainsbury's Superstore - 10 mins walk - Sittingbourne Town Centre - 10 mins walk - Sittingbourne Retail Park - 10 mins walk - Leeds Castle - 35 mins drive

Superhost
Villa in Stockbury
4.87 out of 5 average rating, 101 reviews

The3Squirrels Inn 8 bedrooms 10 beds

Welcome to The3Squirrels Inn in Stockbury, Kent! Experience rustic elegance in our historic pub conversion near a main road set on a large plot of land with no neighbours around. With 8 bedrooms, it's perfect for small groups. Relax in our unique and family-friendly private pub area with antique charm. Plus, unwind in our outdoor hot tub under the stars. Book now for a memorable stay filled with character, warmth, and timeless charm! 2 AC/heater units downstairs to control the temperature

Guest favorite
A cozy seating area features plush, neutral-toned sofas adorned with decorative pillows. A rustic wooden coffee table sits at the center, complementing the warm wooden accents on the walls. Soft lighting creates an inviting ambiance in this thoughtfully designed space.
Farm stay in Oad Street
4.94 out of 5 average rating, 242 reviews

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.

Top guest favorite
Home in Detling
4.98 out of 5 average rating, 140 reviews

Luxury 5-BedRm • Hot Tub • Games Room • Sleeps 12

Kent Downs AONB • Newly renovated 5‑bed group house (sleeps 12 + 2 infants) for friends and family get‑togethers, birthdays and wedding weekends. Flexible sleeping arrangements, private year‑round Hot Tub with views, big games room (pool/TT/foosball + 86" TV + sofa‑bed), Kamado Joe BBQ patio, superfast Wi‑Fi (1gb fibre) + Ethernet, luxury hotel‑quality linen & towels, parking for 7 cars + EV charger. Great for midweek offsites. Easy M20/M2/A249 access + Bearsted train station nearby.

Guest favorite
A view of the two-bedroom annex known as The Little House, surrounded by a grassy area. The structure features a mix of wood and white siding, with a sunny blue sky overhead. Nearby, a parking area is visible, along with a spacious driveway.
Home in Lynsted
4.88 out of 5 average rating, 212 reviews

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.

Top guest favorite
Guesthouse in Medway
4.98 out of 5 average rating, 42 reviews

The Back Garden Annex – Welcoming and Witty

Welcome to Your Cozy Garden Annex in Twydall! Are you visiting family nearby or setting out to explore Kent, the Garden of England? Our charming self-contained garden annex offers a warm, homely space where you can relax, recharge, and feel right at home. Perfectly located in Twydall, just a five-minute drive from Rainham, Kent train station, you’ll have direct links to central London and Kent’s iconic seaside towns — from Whitstable’s oysters to Margate’s sandy shores.

Superhost
Home in Kent
4.95 out of 5 average rating, 37 reviews

Beautiful and Spacious House in Sittingbourne.

Spacious, modern, and thoughtfully designed, this is one of the largest and most comfortable homes you can find in Sittingbourne. Just minutes from the train station, it’s ideal for commuters, families, or longer stays. Enjoy generous living areas and larger than usual outdoor space, fast Wi-Fi, a fully equipped kitchen, and a calm, private estate setting. Whether you’re working, relaxing, or exploring Kent, this home offers space, convenience, and comfort in one place.

Guest favorite
Condo in Kent
4.97 out of 5 average rating, 69 reviews

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.

Top guest favorite
A modern kitchen features sleek cabinetry and a spacious dining table surrounded by several chairs. Essential appliances, including a stove and kettle, are present. Natural light enters through a window, illuminating the countertops adorned with flowers and kitchen items.
Cottage in Borden
4.96 out of 5 average rating, 349 reviews

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.

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