
Guest house holiday rentals in Maidstone District
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Quick stats about guest house rentals in Maidstone District

Total holiday rentals
Explore 40 holiday rentals in Maidstone District

Nightly prices starting at
Maidstone District holiday rentals start at $64 SGD per night before taxes and fees

Verified guest reviews
Over 3,870 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
40 of Maidstone District holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Maidstone District rentals

4.9 Average rating
Maidstone District stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated guest house rentals in Maidstone District
Guests agree: these guest house rentals are highly rated for location, cleanliness and more.

Pear Tree Lodge
Pear Tree Lodge has recently undergone a complete renovation. The property is self- contained from the main house with underfloor heating throughout and mid-century decor. There is a pretty garden exclusively for guests .Keys can be left out so guests can let themselves in and maintain their privacy, we will be on hand should you need anything. The property benefits from its own quiet shale driveway with off street parking. The lodge is a 15 minute walk to the beach, town and the train station.

The Studio, Ticehurst
This fantastic open plan converted office space is located in the heart of High Weald, Area of Outstanding Natural Beauty. ‘The Studio’ is the perfect location for couples or families wanting to explore all that the countryside has to offer. Walking distance from Ticehurst Village, home to Sunday Times Pub of the Year ‘The Bell’. As well as Bewl water, Bedgebury Pinetum, fruit picking & plenty of National Trust properties on the doorstep, you won’t be short of things to do during your stay.

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

The Strawberry Barns near North Downs Way Kent.
Strawberry Barns are your home-away-from-home in the Kent countryside. Surrounded by the quiet of peaceful woodland, in Bramley Acres in Kingswood, near Maidstone. Strawberry Barns are the ideal base for couples to explore the Kent Downs Area of Outstanding Natural Beauty (AONB), North Downs Way, delightful villages, pleasant woodland trails, and lovely pub walks in the countryside, all within a short distance of 500 acres of beautiful parkland and formal gardens at the historic Leeds Castle.

'The Hideaway ' Sole Street, Cobham, Kent.
The Hideaway is situated in the heart of Kent in the rural village of Sole Street, Parish of Cobham & Luddesdown. We are walking distance to Sole Street Station on the Victoria line to London. Ebbsfleet & Meopham are a driving distance away so St Pancras and Victoria can be reached in 17 - 35 minutes. The location is great for people who love long walks & nature as we are surrounded by ancient unspoilt woodlands and rolling hills. We have a choice of three Forestry Commission Parks to visit.

Snap Mill Barn Country Holiday Let
Snap Mill Barn is a recently refurbished one bedroom barn located between Pluckley and Smarden in rural Kent. Surrounded by arable farm land with tranquil surrounding country side with a variety of walks at your doorstep. Open plan living with self contained kitchen, lounge dinner complete with log burner and super fast wifi. Stylish bathroom with enclosed shower and all linen and toiletries provided. Fully enclosed patio area. Many local amenities nearby i.e National Trust properties.

The Stables
Our one bedroom studio is the perfect retreat for two to relax and unwind. Just a short walk from the tree lined high street of Tenterden, with it's eclectic mix of independent shops, historic buildings and small cafes, it is also home to Kent & East Sussex's heritage steam railway. But if relaxing with your favourite glass is more your thing, then it's worth noting, that it is also in the centre of England's wine country, with our local vineyards - from Chapel Down to Gusbourne.

Contemporary rural retreat with breathtaking views
The Rookery is a well located private space with stunning South-facing views across an Area of Outstanding Natural Beauty. An ideal base to explore countryside & coast, ancient forests & villages, historic castles, famous beaches and cosy local pubs. Just 15 min to Sissinghurst Castle & garden, Bodiam & Scotney Castle, 20 min to Rye & 30 min to the dunes & beach at Camber. Explore local walks, Go Ape at Bedgebury Forest, paddleboarding & watersports or tour our local wineries.

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.

Quaint rural 1-bedroom guest house with patio
A peaceful self contained guest house in the grounds of our home. Independent patio, with seating and views over garden, stables and grounds. Our guest house is both cosy and spacious with a fully equipped kitchen. Basics are provided including towels, bread, coffee, tea and fresh bread or croissants. The living area is comfortable and affords a large TV and fast fibre broadband. Everything you need for a relaxing comfortable stay in a truly quiet peaceful environment.

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.

Little Batchelors - Idyllic escape
Set in the grounds of a stunning 400 year old Tudor Hall and gardens, this beautiful new property is 1.5 miles away from the gorgeous Sissinghurst Castle Garden and within easy reach of Biddenden, with its renowned vineyard and Michelin starred restaurant. A perfect setting for couples, small families or friends. It has a very large open plan living/dining/kitchen area with doors onto a decked terrace and two en-suite double bedrooms, with ample room for parking.
Popular amenities for guest house rentals in Maidstone District
Family-friendly guest house rentals

Whispering Waves-Brighton 8 mins/Beach/AC/Parking

Studio Apartment/Annexe

Contemporary 1 bedroom Cabin with secluded Patio

Stylish one-bedroom studio in Appledore, Kent

Wellbeing stay with hot tub near the coast

Alpaca Lodge

Self Contained Garden Studio with stunning views

Sunset View
Guest house rentals with a patio

Double room in detached annex

Barons Granary, The Bull Pen, Iden nr Rye

The Studio House - Crouch End

Oak Tree Cottage

The idyllic Acorn Lodge

The Granary - Luxury conversion in beautiful Kent

Amazing Clockhouse in a perfect location

The Den at Castle Lea
Guest house rentals with a washing machine and dryer

Exclusive use modern barn with stunning views

Watermill, beautiful village of Wye, North Downs

Self Contained Garden Studio near Glyndebourne

Log cabin lakeside retreat in private grounds

Beautifully developed historic stables, high spec

Stylish, Studio Apartment. 5 mins from Eurotunnel.

Jaysbarn charming nook, guesthouse Sussex/Kent

The Annex
When is the best time to visit Maidstone District?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $174 SGD | $172 SGD | $169 SGD | $168 SGD | $177 SGD | $173 SGD | $173 SGD | $174 SGD | $173 SGD | $161 SGD | $163 SGD | $181 SGD |
| Avg. temp | 5°C | 5°C | 7°C | 10°C | 13°C | 16°C | 18°C | 18°C | 15°C | 12°C | 8°C | 6°C |
Destinations to explore
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- Rentals with a washing machine and dryer Maidstone District
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- Paddington
- Covent Garden
- St Pancras International
- British Museum
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