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Vacation rentals in Penwood

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Top-rated vacation rentals in Penwood

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

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Top guest favorite
The exterior of the barn showcases a traditional design with a weathered wooden façade and a pitched roof. Large glass doors provide a view into the interior, while the surrounding area features a gravel pathway and potted plants, set against a backdrop of trees.
Guesthouse in Highclere
4.96 out of 5 average rating, 274 reviews

Hawks Barn: New getaway barn with stunning views.

Hawks Barn is a refurbished, self contained, two bedroom getaway, located a stones throw from Highclere Castle (Downton Abbey). Surrounded by stunning views and walks, the barn is just 10 minutes from Newbury and Whitchurch station to Paddington and Waterloo. Opposite the main house, with parking for 2 cars, the barn has a king bedroom and a twin bedroom, and a small bathroom. Downstairs is a modern sitting room with a 7-seater sofa, large TV, fully fitted kitchen, and a dining and work space.

Guest favorite
The image shows a charming cottage with a thatched roof surrounded by greenery. A gravel pathway leads to the front door, flanked by small shrubs. To the left, a separate annexe is visible, nestled within the well-kept garden and open fields beyond.
Home in Inkpen
4.82 out of 5 average rating, 127 reviews

Brays Cottage, Inkpen - Perfect Country Time...

Inkpen Cottage, just like "the holiday" film, with annexe and extension making it very stylish and quirky. Located at the highest point of the beautiful village of Inkpen just below Combe Gibbett and the Berkshire Downlands. The Cottage is a new house in a seventeenth century beamed one with incredible views from the garden. The countryside is spectacular with more horse, bikes and paragliders passing by than cars...Dog safe Garden! The annexe is ideal for kids / grandparents

Top guest favorite
The exterior of a detached two-story annex featuring grey siding and a large gravel parking area. Solar panels are installed on the roof. Two garage doors are visible, and the main entrance is flanked by two windows, providing natural light to the space.
Apartment in Woolton Hill
4.95 out of 5 average rating, 103 reviews

Self contained en suite room (1 of 2)

Kick back and relax in this calm, quiet, stylish space. Newly completed self-contained, en suite in a detached annex to a country house at the edge of a village. Each flat has AC Heating, Luxury wetroom, Breakfast kitchen (coffee machine), bar to eat or work at. Fast broadband. There is a flatscreen with netflix that you can watch in bed or on our large velvet sofa. Enjoy all year round luxury; great for country walks/pubs, Bike trails and easy access to Newbury, A34 and Highclere castle.

Top guest favorite
The Pigsty features a unique domed structure with a blend of dark and natural wood accents. A small outdoor seating area with a round table and two chairs is positioned at the entrance, surrounded by lush greenery and potted plants.
Hut in Winchester
4.98 out of 5 average rating, 638 reviews

The Pigsty

The Pigsty is Winchester's first luxury woodland hideaway, with beautiful views of Vale Farm. Less than 2.5 miles from the historic centre of Winchester, this peaceful retreat is perfect for those looking to visit the city, or escape for some peace. The Pigsty’s domed design with wooden interior has a roll top bath, cosy open plan living space and decking area to enjoy dinner with sunset views. Just a few minutes walk from the famous Clarendon Way, and a 30 minute walk to the city centre.

Top guest favorite
A bright living area features a spacious gray sofa with red accent pillows and a large checkered ottoman. Skylights provide natural light, while framed art decorates the walls. A dining table is situated nearby, with sliding doors leading to an outdoor terrace.
Home in Pangbourne
5 out of 5 average rating, 255 reviews

A Perfect Pad in Pangbourne!

The house was 'created' in 2020 having originally been part of the village pub - it’s now part of a redeveloped property which also includes the owners home and a fabulous cafe called Artichoke Cafe. The property is right in the heart of the picturesque riverside village of Pangbourne with its fabulous specialist shops, cafes, restaurants and pubs. Yet only ten minutes walk gets you to the countryside! The village also boasts a mainline station with direct trains to London Paddington.

Top guest favorite
A gravelled outdoor area features modern seating arrangements, set against a backdrop of lush greenery and woven fencing. Purple flowers enhance the space, adding a touch of color. The seating area is designed for relaxation and outdoor dining.
Guesthouse in Highclere
4.96 out of 5 average rating, 141 reviews

Lovely self-contained annex with outdoor space

A lovely self-contained annex furnished to a high standard in a quiet rural location on the Berkshire/Hampshire border, close to Newbury and Oxford and walking distance to Highclere Castle (Downton Abbey). Fenced secluded garden area with seating and BBQ for outdoor dining. The Annex is completely separate from our house with its own entrance and there's an allocated parking space for one car. Well behaved dogs are always welcome and there are some lovely walks on our doorstep.

Top guest favorite
The exterior of a barn conversion is presented, showcasing a black wooden facade with a solid wooden door and two wall-mounted lights. The sloped slate roof features varying shades of gray. A green lawn frames the structure, offering a sense of spaciousness.
Barn in Burghclere
5 out of 5 average rating, 34 reviews

Idyllic listed converted barn with tennis court

A stunning 3-bedroom barn conversion nestled in the heart of rural Hampshire, this unique home blends rustic charm with luxury living. Lovingly restored and decorated to an exceptional standard, it features open-plan living, exposed beams, and high-end finishes throughout. Surrounded by countryside, it's a tranquil retreat with modern elegance—perfect for those seeking style, comfort, and serenity with access to a tennis court, plenty of walks and pubs directly from your door.

Top guest favorite
A gravel parking area is visible in front of a two-story annexe, framed by frost-covered grass. Two cars are parked near the building, which features a wooden facade and large garage doors. A tree stands nearby, contributing to the tranquil outdoor setting.
Guesthouse in Penton Mewsey
4.97 out of 5 average rating, 208 reviews

Peaceful private annexe with far-reaching views

The first floor annexe is accessed via a covered external staircase. Home from home, cosy but spacious one bed (2 guests) accommodation with living space and kitchen. The balcony is perfect for morning coffee/evening drinks (weather allowing) with far reaching views over the Hampshire countryside. The annexe is adjacent to our home but is entirely private for guests' exclusive use. We will welcome you, and can answer any questions but we will also respect your privacy.

Guest favorite
An A-frame structure is framed by trees and surrounded by blooming bluebells. Light filters through the open front, illuminating the interior where a seating area is presented. The natural setting offers a serene escape, with vibrant flowers in the foreground enhancing the tranquil scene.
Hut in Ovington
4.97 out of 5 average rating, 167 reviews

The Glade at Ladyhill Vineyard near Winchester

Nestled on the edge of an ancient wood in South Downs National Park and with fantastic views over Ladyhill Vineyard and the Hampshire countryside The Glade has a cosy A-Frame to grab a good night sleep, a separate shower room with flushable loo to keep you fresh and a kitchen equip-for-easy glamping. Relax and admire the views, BBQ on the fire pit, spot deer and hare or stroll down the river Itchen to The Bush gastro pub. You’ll return home totally refreshed!

Top guest favorite
A charming thatched cottage is surrounded by green grass and trees. The rustic structure features a wooden exterior and multiple windows that provide natural light. A simple picket fence adds to the character of the property, enhancing the rural ambiance.
Barn in Ecchinswell
4.92 out of 5 average rating, 404 reviews

The Pigsty

Escape to a tranquil rural setting in the heart of the Hampshire countryside and in the shadow of Watership Down. Beautiful self-contained accommodation surrounded by gardens in a historic village with easy access to a multitude of walks and local amenities. Nearby attractions include Highclere Castle, Greenham Common, Stone Henge, Newbury and Winchester. Oxford (35 miles), Bath (70 miles) and London 45 minutes on the train from Newbury or Basingstoke.

Top guest favorite
The cottage exterior features a traditional thatched roof, blending with the whitewashed walls. A green wooden door is flanked by a small window, which allows natural light to enter. A lantern hangs beside the door, providing a charming touch to the entrance.
Cottage in Ashford Hill
4.94 out of 5 average rating, 354 reviews

Thatched Grade ll property in Ashford Hill

A detached, Grade ll, 200 year old thatched cottage in the small village of Ashford Hill, close to Newbury. My husband Andy and I own this one bedroom cottage, which has been carefully furnished and has parking and a small dedicated outdoor space.. It is an ideal base to explore the local area. Guests can visit Highclere Castle (Downton Abbey), attend the races at Newbury Race Course or enjoy the walks in the surrounding area including Watership Down.

Top guest favorite
An aerial view captures the Pool House surrounded by lush greenery. A modern pool and hot tub are positioned alongside comfortable loungers on a spacious patio. The sliding glass doors of the house provide access to an inviting indoor area.
Guesthouse in Garsington
4.95 out of 5 average rating, 549 reviews

The Pool House

Relax and reset at the Pool House. The Pool House provides a quiet location where you can relax away from the world. Swim in our pool, heated during the warmer months. During the colder months enjoy a cold plunge, beneficial for body and mind. Ease your aches and muscles in the hot tub. Please note: you are using the pool and hot tub at your own risk, there is no life guard! Please watch children and non swimmers in the pool and hot tub at all times.

Popular amenities for Penwood vacation rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Hampshire
  5. Penwood