Vacation rentals in Guestling

The Woolly Retreat - Alpaca Shepherds Hut.

Nestled in a secluded Alpaca field in the heart of the enchanting Ashdown Forest lies a cosy, new Shepherd’s Hut in the idyllic village of Hartfield, famous for its connection to Winnie the Pooh and his timeless adventures. Surrounded by Alpacas which you can feed , this charming retreat offers a perfect blend of rustic luxury & nature. Whether you're looking for a romantic getaway, or just a relaxing weekend immersed in nature, our shepherd's hut is the place to unwind, recharge and reconnect.

Pebbles - a calm and peaceful retreat near the sea

Pebbles is a private annexe at our home in Pett Level, a haven of peace and calmness. You’ll be only five minutes walk from an amazing beach. Surrounded by beautiful countryside and cliff top walks, 2 local pubs in the village of Pett, 5 minutes car ride or a lovely 1/2 hour walk away over the hills. There is a bright lounge with french doors overlooking the garden, wet room, double bedroom and fully fitted kitchen. The garden is secluded and peaceful . The beautiful town of Rye is 5 miles away.

The Lodge & Tennis Court

One of two available properties at the same location (Club House) the Lodge was Airbnb #12 most Wish Listed homes for Britons in 2021. Set in the grounds of a Traditional Sussex Farmhouse with far reaching views, you will experience a unique boutique hotel experience with a sense of an Alpine stay. A spacious open plan layout and beautifully finished cosy interior with lots of personal touches to make your stay a unique one. Add a Private Tennis Court, and you will have a most memorable break

Sunny single-level cottage • Dogs • Near Rye

Escape to our bright, single-level Sussex cottage, perfect for relaxed coastal breaks with family, friends, or older relatives. Minutes from the sea, historic Rye and trendy Hastings, the cottage offers a sunny interior, enclosed garden, parking and a peaceful setting ideal for unwinding after coastal walks or countryside days out. Dog-friendly and thoughtfully laid out with no stairs, it’s an easy and comfortable base for exploring the best of East Sussex, from beaches to charming villages.

Log cabin lakeside retreat in private grounds

Take it easy at this unique and tranquil getaway. Set in private grounds of 10.5 acres & shared only with the on-site owners, this Log Cabin overlooks the lower lake Bedroom 1 features a huge Emperor Size double bed (7ft x 7ft), with duck down Egyptian cotton pillows and duvet. Double doors open to a balcony overlooking the lake Bedroom 2 - 2 Single Hypnos medium mattresses or 1 x Super King bed Includes two further fold out beds best suited for children. Outdoors: 1 x balcony 3 x patio

Big barn, Nr Hastings/Rye 4 doubles 1 bunk room

Our Barn is a large, rustic , comfy home situated in a semi -rural location 10 mins drive from the vibrant seaside town of Hastings in one direction and Rye in the other, close to main road. The perfect place to really relax and explore the breathtaking surroundings. With fascinating places to visit, stunning beaches, award winning restaurants and pubs, quirky shops and easy access to Brighton, Lewes and Kent.We have 4 Double Bedrooms (1 on ground floor) and 1 small kids room with bunk beds.

Flat in St. Leonards on Sea

Come stay in St Leonards on Sea in this tasteful, spacious 1-bedroom basement flat, part of a beautiful Georgian terrace. Stylishly decorated, the flat features a double bedroom, modern bathroom, a living room, with a table and chairs, a fully-equipped kitchen and french doors leading to a private patio. Located just a 5-minute walk from the beach, Warrior Square Station, and the vibrant restaurants, cafes, and shops of St. Leonard's, this flat is perfect for a relaxing coastal getaway.

Escape to the Sea

Gorgeous, spacious, south-facing flat with stunning sea views, original features, and high ceilings. The sunrises/sets and moon reflections are breathtaking! In between St Leonards on Sea and Hastings, and 30 seconds to the beach! The bedroom has a king size bed and the living room a double sofabed. Bedding is cotton/linen washed with non toxic products. Flat is on the 3rd floor but not that many stairs and as such, sea views far from the madding crowd! There is free parking nearby

Delightful 2 bedroom hideaway close to beach

Woodview is ideal for a romantic get away by the sea or a bird-watching holiday on the wonderful Rye Harbour Nature Reserve. This cosy cottage has free parking on site and lots of secluded outdoor space with a range of seating and dining areas. Recently refurbished throughout, it has a well-equipped new kitchen and shower room. Winchelsea Beach Village has good amenities and is close to a wide range of local historic and countryside attractions that can be enjoyed all year round.

The Annex

A two bedroom self-contained cottage set in the East Sussex countryside, with views of the Fairlight Hall Estate and the English Channel. On a clear day you can see as far as Dungeness and the inter-lying beaches. Situated between the historic old fishing port of Hastings and the fortified hilltop town of Rye, on the A259. The Annex is next door to a family home within their established garden, to which guests have access. The nearest railway stations are Battle or Hastings.

Relaxing Luxury Retreat

Hop Pickers Retreat is found in the heart of an Area of Outstanding Natural Beauty (AONB) on the Kent and East Sussex border. Located on an farm you are surrounded by wildlife, birdsong, mooing cows, stunning views and in the summertime the sound of a combine, combining the crops in the surrounding fields. It is the ideal place to turn off that phone and unwind with your glass of your favourite tipple in the woodfired hot tub underneath the big starry sky.

Old Smock Windmill in rural Kent

Old Smock Mill is a romantic place for couples. The atmosphere inside is peaceful and relaxing. Everything is designed to unwind you from the moment you walk in. It is surrounded by the lovely Kent countryside where you can ramble and refresh yourselves by perhaps ending the day in one of the great pubs cosy by a log fire in Winter or in Summer in an English garden. Guests have said how hard it is to tear themselves away, it truly is a treasure to find.