Vacation rentals in Maidstone

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Top-rated vacation rentals in Maidstone

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Guest favorite

Barn in Linton

4.87 out of 5 average rating, 258 reviews

Chimney Barn

Chimney Barn is on the grounds of a Grade II listed (450 yr old) property in a conservation area (rural setting) just outside Maidstone, Chimney Barn is close to Linton Park House, Estate, built in the 1730’s and now owned by an international agricultural company. The park has lots of Stunning walks throughout the country side, over looking Marden and the surrounding areas. The Bull Inn is also within walking distance and a very popular local pub and restaurant, with garden and stunning views.

Dec 30 – Jan 6

R1,733 ZAR per night

Guest favorite

Guesthouse in Detling

4.92 out of 5 average rating, 130 reviews

Adorable 1 bed guesthouse with patio

Sit back & relax in this calm, cosy space. Set within the grounds of our gated family home in Detling located on the slope of the North Downs, 4 miles north east of Maidstone, & on the Pilgrims' Way. Whether you want a relaxing get away or want to explore many of the wonderful walks and bike trails the north downs have to offer you can be sure to find a warm and cosy place to stay at the end of the day. We have a very friendly dog who will be on hand to greet you along with 2 young children

Apr 5 – 12

R2,329 ZAR per night

Guest favorite

Farm stay in Kent

4.99 out of 5 average rating, 343 reviews

Traditional Log Cabin On The Lake

Private cosy traditional log cabin on the lake, surrounded by beautiful countryside. Lovely peaceful get away from it all in an area of natural outstanding beauty, yet just ten minutes drive from Royal Tunbridge Wells, with all the culture, bars, restaurants and shops. The pretty village of Lamberhurst has lots of pubs to offer, with top quality food and local ales. Trains to London are 1 hour from Frant station. Nearby attractions include Scotney Castle, Bewl Water and Bedgebury Pinetum.

Oct 7 – 14

R3,008 ZAR per night

Guest favorite

Cabin in Rochester

4.94 out of 5 average rating, 265 reviews

Countryside Cabin with Private Patio

The Snuggery is a converted outbuilding that has been set up for a cosy stay with a wood burning stove and lots of snuggly wraps to cuddle up in. The open plan interior, high vaulted ceilings and natural oak flooring create an interior which is fun, light and airy. Walking enthusiasts will enjoy walks from the back door straight on to the North Downs Way and there is a bench by the front door fitted with a heated element, perfect for warming up your walking boots. Photos by Chloe-Rae

Sep 25 – Oct 2

R2,625 ZAR per night

Guest favorite

Guesthouse in Kings Hill

4.96 out of 5 average rating, 182 reviews

Peaceful, charming oak framed annexe

Recently furbished, oak framed annexe building consisting of large open plan lounge, dining and kitchen area. Shower room with hand basin and WC. Upstairs, snug double bedroom. (May be converted to two singles) Extra sofa bed available downstairs so property can accommodate up to 4 guests. Reliable wifi and space for remote working. Small, discreet private patio area. Private parking. Close to golf course and village centre. Surround yourself with style in this standout space.

Dec 23 – 30

R2,939 ZAR per night

Guest favorite

Houseboat in Kent

4.92 out of 5 average rating, 123 reviews

Lady Florence unique River Boat with Castle Views

Lady Florence is a new unique houseboat, situated on the River Medway in Maidstone. Is surrounded by breath-taking views of Allington Castle, in a quiet location. A great place to escape everyday life and unwind. The houseboat offers a fully fitted bathroom with shower, Modern kitchen supplied with all the necessary utensils, double bedroom area, pull out sofa bed that will sleep 2, terrace either end with outdoor seating, WIFI and Smart TVs. Local area has lots to offer.

Apr 24 – May 1

R3,076 ZAR per night

Guest favorite

Guesthouse in Boughton Monchelsea

4.96 out of 5 average rating, 138 reviews

Adorable 1 bedroom guest barn, Boughton Monchelsea

This barn is situated in the picturesque village of Boughton Monchelsea. It has its own private garden with stunning meadow views. It has lots of local amenities to explore and is only 15 minutes drive from Leeds castle and a 15 minute drive to the train station which will take you directly into London. The exposed oak beamed barn is situated next to a traditional oast house, perfect for romantic getaways and people who want to escape the fast pace of everyday life.

Dec 6 – 13

R2,324 ZAR per night

Guest favorite

Cottage in Boughton Monchelsea

4.91 out of 5 average rating, 510 reviews

The Oast Cottage: Private Annex with own entrance.

We are pleased to offer our refurbished annex with double bedroom, private bathroom, own front door and a private field for dogs. Oast Cottage is a converted stables attached to the main Oast House. The Oast is set in a conservation area of Boughton Monchelsea which consists of converted farm buildings, listed houses and a 16th Century pub (directly opposite). The area boasts many places to visit (including Leeds Castle), countryside walks, as well as numerous pubs.

Apr 11 – 18

R1,794 ZAR per night

Guest favorite

Guest suite in Wateringbury

4.98 out of 5 average rating, 166 reviews

Peaceful apt, views, Wi-Fi, garden & sunsets

Relax or work in this stylish apartment with private courtyard garden and vintage summerhouse * First floor apartment with free parking * Rural views * Wi-Fi * Self check in * 6ft super king bed * Heating * Smart TV * Plus a summerhouse * Under 1 hour train from London * Local pub/food 10 minute walk * Close to country walks * River Medway 1 mile for boating/walks * Not suitable for pets or children * Please note EV charging is NOT permitted on the property*

Aug 4 – 11

R2,739 ZAR per night

Guest favorite

Home in Kent

4.93 out of 5 average rating, 216 reviews

Hermitage Cottage cosy 1-4 person accommodation.

Hermitage Cottage offers annexe accommodation. Bathed in sunshine in private garden setting. We are a commuters dream with Barming railway station at the door. London Victoria 57 minutes and Maidstone East just three minutes by rail. Fully fenced with garaging for one vehicle., entry by automatic gates. Finished to a very high standard with under floor heating and feature fire place. Your every comfort is assured. Welcome pack included.

Oct 22 – 29

R2,026 ZAR per night

Guest favorite

Cottage in Marden

4.99 out of 5 average rating, 476 reviews

The Lodge

**Opted in to Airbnb's enhanced cleaning protocol** Cosy barn-style accommodation nestled in the heart of the Kent countryside. Located close to National Trust sites and country walks. The Lodge is the perfect country getaway and romantic retreat. Please note this is strictly a NO SMOKING property inside the Lodge, the garden and surrounding field. The property is also NOT SUITABLE for infants, children or pets. Two adults only.

Oct 17 – 24

R2,001 ZAR per night

Guest favorite

Guesthouse in Kent

4.98 out of 5 average rating, 237 reviews

The Old Engineer, a rural boutique retreat

Our rural boutique accommodation with private entrance and pretty courtyard garden is surrounded by fields. The space is designed with the guests comfort and luxury in mind. It is the perfect spot for a relaxing and peaceful get away. Super king bed (or twin if requested). Located between Tunbridge Wells and Maidstone, close to the Hop Farm and attractions such as Sissinghurst Gardens, Vineyards and many NT properties.

Feb 12 – 19

R2,524 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Maidstone vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Maidstone's top sights

Mote Park37 locals recommend

The Mall10 locals recommend

Maidstone Leisure Centre3 locals recommend

Lockmeadow Entertainment Centre5 locals recommend

Morrisons8 locals recommend

ALDI4 locals recommend

Other great vacation rentals in Maidstone

Guest favorite

Cabin in Maidstone, Kent

4.94 out of 5 average rating, 501 reviews

Cosy Woodland Lodge with your own alfresco Hot Tub

Dec 18 – 25

R3,569 ZAR per night

Guest favorite

Condo in Thorpe Bay

4.99 out of 5 average rating, 277 reviews

Estuary Views Penthouse with Parking

Jan 13 – 20

R3,617 ZAR per night

Guest favorite

Cabin in Medway

4.91 out of 5 average rating, 231 reviews

Peaceful 2 bedroom country lodge

Apr 10 – 17

R2,014 ZAR per night

Guest favorite

Apartment in Kent

4.96 out of 5 average rating, 185 reviews

Georgian house, ten minutes from the beach.

Oct 23 – 30

R2,020 ZAR per night

Guest favorite

Guesthouse in Tonbridge

4.95 out of 5 average rating, 194 reviews

Weald Lodge: self-contained annexe with parking

Jun 6 – 13

R2,248 ZAR per night

Guest favorite

Cottage in Sandhurst

5.0 out of 5 average rating, 321 reviews

Cosy Cottage with Woodburner & Countryside Views.

Mar 8 – 15

R2,724 ZAR per night

Guest favorite

Hut in Horsmonden

5.0 out of 5 average rating, 208 reviews

Railwayman's Hut with Swimming Pond

Mar 23 – 30

R2,303 ZAR per night

Guest favorite

Place to stay in Addington

4.98 out of 5 average rating, 161 reviews

Petite Gite in an idyllic cottage garden.

Aug 9 – 16

R1,588 ZAR per night

Show all

Quick stats about vacation rentals in Maidstone

Total rentals
250 properties
Wifi availability
230 properties include access to wifi
Rentals with dedicated workspaces
150 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
4K reviews

Frequently Asked Questions

What are the most popular amenities for Apartment Rentals in Maidstone?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with free parking, over 70 homes with a kitchen, over 70 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Where should I stay in Maidstone?
Make yourself at home in Maidstone by choosing from our most frequently booked neighborhoods. We have over 240 vacation rentals in Penenden Heath, over 40 vacation rentals in Detling, over 100 vacation rentals in East Farleigh, and over 290 vacation rentals in Weavering.
Do condo rentals in Maidstone have a kitchen?
Absolutely! We offer over 20 condo rentals with a kitchen in Maidstone. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Maidstone have free parking?
Absolutely! We offer over 30 apartment rentals with free parking in Maidstone. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Maidstone?
Yes! Work meets play with ease at over 150 vacation rentals in Maidstone featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Maidstone?
Four-legged friends are welcome in Maidstone. Choose from more than 50 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Maidstone?
Maidstone has more than 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in condo rentals in Maidstone?
Experience the best of Maidstone with our condo rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Vacation rentals in Maidstone

Top-rated vacation rentals in Maidstone

Vacation rentals for every style

Cottages

Houses

Apartments

Popular amenities for Maidstone vacation rentals

Stay near Maidstone's top sights

Other great vacation rentals in Maidstone

Cabin in Maidstone, Kent

Condo in Thorpe Bay

Cabin in Medway

Apartment in Kent

Guesthouse in Tonbridge

Cottage in Sandhurst

Hut in Horsmonden

Place to stay in Addington

Quick stats about vacation rentals in Maidstone

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

What are the most popular amenities for Apartment Rentals in Maidstone?

Where should I stay in Maidstone?

Do condo rentals in Maidstone have a kitchen?

Do apartment rentals in Maidstone have free parking?

Are there vacation rentals with a dedicated workspace in Maidstone?

Are there pet-friendly vacation rentals in Maidstone?

Are there family-friendly vacation rentals in Maidstone?

How much does it cost to stay in condo rentals in Maidstone?

Destinations to explore