Vacation rentals in Maidstone

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Maidstone

  • Total vacation rentals

    Explore 320 vacation rentals in Maidstone

  • Nightly prices starting at

    Maidstone vacation rentals start at G$4,177 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,720 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    180 properties have a dedicated workspace

  • Wi-Fi availability

    300 of Maidstone vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Maidstone rentals

  • 4.6 Average rating

    Maidstone stays receive an average rating of 4.6 out of 5 from guests

Top-rated vacation rentals in Maidstone

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The modern countryside house features a striking angular design with large glass panels reflecting the sky. A spacious lawn surrounds the property, complemented by a patio and outdoor seating area. Lush greenery provides a natural border, enhancing the tranquil outdoor setting.
Barn in Sutton Valence
4.96 out of 5 average rating, 142 reviews

The Barnyard

Kick back and relax in this calm and stylish architecturally designed countryside home. Recently built, with the focus on creating a high end holiday home which has been equipped to a very high standard. Situated in the heart of the wine producing area of the Kent countryside, with many local pubs and restaurants only a gentle stroll away. The beautiful contemporary design, with vaulted ceilings and polished concrete floors serve to provide a relaxing and stylish vacation for up to six guests.

ValueFamilyBathroom

Superhost
A charming brick cottage is adorned with blooming wisteria, cascading over the windows. The well-maintained exterior features white window frames, enhancing the rustic aesthetic. Lush greenery surrounds the entrance, creating an inviting atmosphere for guests.
Cottage in Cobham
4.84 out of 5 average rating, 517 reviews

Countryside Escape in Beautiful Cosy Cottage

Wisteria Cottage is a beautiful four bedroom, listed building, set in an idyllic historic village. Perfect setting for family holiday or for people who enjoy the countryside and glorious walks. Bluewater is close by. Wisteria cottage is great for those wanting a getaway that offers nearby vibrant city as well as beautiful countryside. We have recently modernised the cottage, it’s a brilliant space! We have put a climbing frame in the garden for hours of fun for the little ones. Relax and enjoy.

FamilyLocationHospitality

Guest favorite
The charming exterior of a three-story house features painted walls and multiple windows that allow ample natural light. Lush greenery and well-kept shrubs surround the front garden, while a quiet road lined with gravel adds a peaceful atmosphere to the setting.
Cottage in Sandling
4.95 out of 5 average rating, 57 reviews

Beautiful 3/4 bed Cottage perfectly sited in Kent

Relax at our delightful listed home dating back to the seventeenth century bursting with character and history. Close to all transport links to London 50 mins, 40 mins to the coast and the Chunnel and only 20 minutes from Brands Hatch . Set on the edge of beautiful countryside opposite a Mill Pond close to the Pilgrims Way and hillside vineyards . Great local pubs and restaurants within 400 metres and Maidstone town and all its amenities is also a short walk away a long the scenic River Medway

LocationFamilyOutdoor spaces

Top guest favorite
The exterior of a stone cottage is presented, featuring a balcony with a glass railing overlooking the river. Lush greenery surrounds the property, with a wooden jetty in the foreground, adding to the tranquil riverside setting.
Home in Maidstone
5.0 out of 5 average rating, 204 reviews

Riverside Cottage , Maidstone

Open plan Luxury Cottage with balcony over looking the river and nearby lock. Traditional Barges moor along this part of the river. The Market town is a 20 minute walk along a picturesque tow path or a few minutes drive. There are several Bar/Restaurants a short walk away . Ideal area for all age groups. Comfortably furnished and well equipped. Four Lovely Bedrooms, two with original stone walls. Two Shower Ensuite's and a family Bathroom. Two outside courtyards and Plenty of parking.

FamilyLocationKitchen

Superhost
A modern kitchen area features sleek dark cabinetry and stainless steel appliances, including an oven and microwave. Two pendant lights hang above a wooden bar with seating for two. A light gray sofa is positioned nearby, complemented by an orange decorative pillow.
Apartment in Kent
4.88 out of 5 average rating, 137 reviews

The Bohemian Basement

The Bohemian Basement is a unique stylish one bed apartment with its own private garden in the heart of Maidstone. The apartment is 1 of 3 within a newly converted Victorian property just minutes walk from the town centres shops, restaurants and bars. Perfectly equipped with everything you’ll need while visiting Maidstone and with the added bonus of having a wonderful private outdoor garden space, makes this a fantastic Airbnb. There is free on street permit parking which we supply.

ValueFamilyCleanliness

Top guest favorite
Home in Hunton
5.0 out of 5 average rating, 117 reviews

Peaceful guest home at Primrose Place

Primrose Place is a self-contained, private annexe to our home with its own parking space. There is a good sized bedroom with a king sized bed, a large bathroom and a kitchen/lounge with its own enclosed patio. The sofa bed in the lounge provides an additional double bed. Primrose Place is straddled on the edge of two villages so it benefits from being a few minutes walk through the woods to the Greensand Way and surrounding countryside and also a paved walk to local shops and amenities.

ValueFamilyBreakfast

Top guest favorite
Home in Detling
4.98 out of 5 average rating, 144 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.

LocationValueHospitality

Top guest favorite
Cottage in Yalding
4.99 out of 5 average rating, 145 reviews

Gather&Unwind: Gardens, Woodland & Tennis Cottages

Two charming 3-bedroom cottages with private en-suite bathrooms, set within 2.5 acres of Kentish gardens and woodland. Enjoy a tennis court, children’s play area, walking trails and an in-house ice cream parlour stocked with local Taywell Kentish ice cream. Make your own old-fashioned candyfloss and buttery cinema-style popcorn. Perfect for families, friends and wedding guests. Dog-friendly, with historic Yalding village nearby and London just 45 minutes away by train.

LocationValueBackyard

Guest favorite
An exterior view of a barn features a neatly maintained lawn, framed by a stone structure. Double glass doors lead into the barn. Two small chairs are positioned on a paved patio area near the entrance, inviting relaxation. Surrounding greenery adds a natural touch.
Guesthouse in Boughton Monchelsea
4.97 out of 5 average rating, 369 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.

LocationValueDecor

Guest favorite
The exterior of the annex is presented, featuring a white picket fence and a gravel area. A vintage lamppost stands near the entrance, complemented by two outdoor chairs positioned on the patio. The structure showcases a pitched roof, rustic siding, and several windows, providing ample natural light.
Cottage in Boughton Monchelsea
4.89 out of 5 average rating, 944 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.

FamilyValueCheckout

Guest favorite
A well-lit bedroom features a spacious bed with a combination of white and orange bedding. Two framed artworks are mounted on the wall above the headboard. Natural light streams in from a large window, which offers a view of the surrounding area.
Bungalow in Kent
4.97 out of 5 average rating, 127 reviews

Maidstone Bungalow sleeps 5 with parking

This stylish bungalow boasts with unique features and has everything you need for a comfortable stay. Open plan living space is airy and bright and compliments fully equipped modern kitchen. This 2 bed fully refurbished single level home sleeps up to 5 people and it can provide both king size and single beds. The bungalow is located in a prominent position in Allington, Maidstone, and it offers off road parking for multiple cars and a private garden.

ValueFamilySleep quality

Guest favorite
Home in Kent
4.91 out of 5 average rating, 336 reviews

Hermitage Cottage 2 Guests 2 Children.

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.

LocationFamilyCleanliness

Popular amenities for Maidstone vacation rentals

When is the best time to visit Maidstone?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,494 GYDG$30,285 GYDG$29,032 GYDG$30,076 GYDG$33,209 GYDG$30,912 GYDG$33,209 GYDG$34,671 GYDG$31,330 GYDG$30,076 GYDG$27,361 GYDG$30,494 GYD
Avg. temp5°C5°C7°C10°C13°C16°C18°C18°C15°C12°C8°C6°C

Frequently Asked Questions

  • What are the best places to stay in Maidstone?

    Central Maidstone neighborhoods have convenient access to shops, dining, and riverside walks, while nearby villages provide quieter, scenic stays. Both options make it easy to explore the area's history and parks.

  • What are the best things to do in Maidstone with kids?

    Children often enjoy exploring Maidstone's parks, botanical gardens, and interactive museums. Many families spend time at animal centers or participating in outdoor adventure activities.

  • What are some of the best things to do in Maidstone?

    Explore castles, stroll riverside parks, and visit museums that highlight local heritage. Many visitors enjoy discovering gardens and sampling Kentish cuisine at local markets or cafés.

  • How is the weather in Maidstone?

    Maidstone has cool winters around 36–47°F (2–9°C) with occasional rain and milder summers averaging 55–73°F (13–23°C). Light layers and a waterproof jacket make it easier to adjust to changeable weather throughout the year.

  • When is the best time to visit Maidstone?

    Late spring through early autumn is frequently suggested for milder weather and an active events calendar. These months highlight blooming gardens and outdoor activities across Maidstone.

  • What are the best places to visit in Maidstone?

    Popular places to visit include Leeds Castle, Mote Park, and the Maidstone Museum. Historic estates and tranquil gardens are also often recommended for a balanced visit.

  • What are some hiking trails in Maidstone?

    Maidstone has walking paths along the River Medway, and nearby woodlands with marked trails suitable for various fitness levels. Parks and nature reserves around the area can be a good starting point for local hikes.

  • What are some family activities we can do in Maidstone?

    Families often explore animal parks, hands-on museums, and play areas in Maidstone’s parks. Cycle paths and activity centers around the area provide active ways to spend the day together.

  • What are some of the best day trip ideas from Maidstone?

    Consider exploring Kentish villages, coastal towns, or historic market areas around Maidstone. Vineyards and walking trails in the surrounding countryside are frequently suggested as day trips.

  • Are there any pet friendly accommodations available in Maidstone?

    Pet friendly accommodations are available in various parts of Maidstone, including both town and countryside settings. Parks and riverside walks make it an enjoyable place to travel with pets.

  • What are some local tips for visiting Maidstone?

    Explore river paths and parks around the town center, and consider local markets for regional products. Comfortable shoes are helpful, as Maidstone has several historic sites and gardens best enjoyed on foot.

  • What is Maidstone known for?

    Maidstone is known for its historic castles, riverside walks, and vibrant local markets. The area has connections to the hop-growing traditions of the Kent countryside.

  • What are the best hidden gems to explore in Maidstone?

    Smaller museums, independent art spaces, and riverside parks are often mentioned as hidden gems in Maidstone. The nearby countryside has quiet woodlands and nature areas for a peaceful outing.

  • What are the best foods to try in Maidstone?

    Maidstone has dishes featuring locally grown produce, traditional Kentish pies, and artisan ciders. You may also find regional cheeses and baked treats at farmers’ markets or local bakeries.

  • What should I bring for a trip to Maidstone?

    Pack comfortable walking shoes, a waterproof jacket, and adaptable layers to match variable temperatures. A reusable water bottle and a small daypack are helpful for exploring parks and historic sites.

  • What is the nightlife in Maidstone like?

    Maidstone’s nightlife scene includes lively pubs, bars, live music venues, and periodic seasonal events. Locals often gather in the town center and along the riverside for entertainment.

  • What are the most popular events or festivals in Maidstone?

    Maidstone often hosts food and drink festivals, live music celebrations, and agricultural shows, especially in warmer months. The area is also known for recurring cultural events and seasonal fairs.

  • Are there family friendly vacation rentals in Maidstone?

    Family friendly vacation rentals can be found across Maidstone, with a mix of neighborhoods and rural surroundings. Many homes have features such as gardens or extra rooms tailored for group stays.