Holiday rentals in Upwey

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Top-rated holiday rentals in Upwey

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Guest favourite

The wooden clad hut is set against a stone wall in a green field. A white door is framed by flower pots and decorative features. A railing surrounds the entrance, with a small outdoor seating area visible. Lush grass and trees complement the natural setting.

Hut in Weymouth

Batch Hut (Dog Friendly but just one please)

Wooden clad hut set in the heart of Upwey village, it’s similar to a Shepherd's Hut but slightly bigger. The hut is sited in a field only 3 minutes walk from two local pubs, set on the Jurassic Trail so country walks in abundance, 5 min drive to Weymouth Beach. This is ideally suited for those wanting down to earth but acceptable accommodation. Everybody who has stayed here has really enjoyed the country setting and although basic I have been told many times that the photos don't do it justice.

4.92 out of 5 average rating, 208 reviews

Top guest favourite

The exterior of a late Victorian house is shown, featuring a brick facade with decorative elements. The property is surrounded by well-maintained greenery, including a lawn and trees. Several windows, evenly spaced, provide views into the building, complementing the architectural details.

Apartment in Dorchester

Large 2 bedroom town centre flat with free parking

Located overlooking Dorchester’s beautiful, tranquil Borough Gardens, this very spacious two bedroom flat provides the perfect place to enjoy a break in splendid Dorset’s historic county town. The property is only a two minute walk from the main high street of the town with its shops, museums and historic buildings. It is also within easy, level walking distance to the two train stations and many bus routes. A free parking space included allows guests to visit all areas of the county with ease.

4.99 out of 5 average rating, 146 reviews

Top guest favourite

An open living space features a warm color palette with stone walls and wooden beams. A leather sofa is positioned in front of a wood-burning stove, enhancing comfort. A dining area with two chairs is visible, as well as a well-equipped kitchen with modern appliances.

Barn in Dorchester

The Cowshed, Washing Pool Barns - suite for two

Luxurious Dorset village suite for two. Quality conversion of a listed stone barn into a completely equipped ground floor self-catering suite in the Dorset AONB. A couple of miles south west of Dorchester Washing Pool Barns are in the heart of Martinstown village, just a one minute walk from the local pub and maybe five minutes walk to the village store and post office. Bridleways, cycle routes and public footpaths are on the doorstep with the Jurassic coastline around five miles further south.

5.0 out of 5 average rating, 101 reviews

Top guest favourite

A stone cottage features a light green door framed by greenery. Large windows allow natural light to illuminate the entryway, while shrubs and trees create a peaceful, sheltered setting. The roofline peaks gently against a backdrop of clear blue skies.

Home in Martinstown

Enchanting Manor Coach House

An elegant, relaxed home in the grounds of the Manor in this AONB with walks directly from the house. The pretty village of Winterbourne St. Martin (Martinstown) has a great pub and a super village shop both within a short walk. Close to the Jurassic Coast and spectacular country views, its the perfect place to chill after a walk, a day at the beach (approx five miles away) or visiting the many attractions in and around Dorchester. Guests have a private garden, and access to a tennis court.

4.96 out of 5 average rating, 142 reviews

Top guest favourite

A modern kitchen features a wooden dining table surrounded by four woven chairs. A large range cooker is positioned against the tiled backsplash, with ample white cabinetry overhead and below. Open shelving displays glassware and decorative items, complemented by soft lighting and a neutral-colored floor.

Cottage in Weymouth

Strawberry Cottage

Lovingly restored and modernised by Harry in 2011, Strawberry Cottage is nestled by the river Wey in the village of Upwey, Dorset. This quaint property is close to the famous Jurassic Coast, within 4 miles of the seaside town of Weymouth and Dorchester town.Durdle Door / Lulworth Cove is an approximate 29 minute drive,and the main supermarket is 8 minutes away by car. Upwey has two pubs a busy tearoom,garden nursery and Tesco Express all within 5 to 10 minutes walk. Relax inside or out.

4.95 out of 5 average rating, 248 reviews

Guest favourite

The entrance features a maroon double door with decorative panels and shuttered windows. A small green table and chair set are positioned on the patio, surrounded by potted plants with blooming flowers. A house number plaque is mounted nearby.

Apartment in Dorchester

Studio with off-street parking, private entrance

Welcome to our bright studio with gated off-road parking and free fibre wi-fi. We welcome all to enjoy a stay in Dorset. We are a ten minute walk from the station, Poundbury and Brewery Square. Our newly renovated studio has an inviting interior, a rainfall shower and dedicated office space. A small double bed will provide a comfortable nights sleep. If booking for someone else please provide passport details and previous reviews as they may not have been verified. Minimum stay two nights

4.9 out of 5 average rating, 124 reviews

Top guest favourite

The entrance features a charming brick façade with large windows, allowing natural light to fill the space. A wooden bench is positioned near the front door, surrounded by potted plants that enhance the welcoming ambiance.

Cottage in Dorset

No1. The Courtyard, Clyffe House

Enjoy a tranquil break in our recently renovated Grade II listed cottage in the heart of Dorset. No.1 The Courtyard is nestled just outside the village of Tincleton and was originally part of the servant’s accommodation to Clyffe House (1842). We are situated 6 miles from Dorchester, and within easy reach of many Dorset attractions; Lulworth Cove, Durdle Door, Corfe Castle, The Purbeck Hills, Kimmeridge, Southwest Coastal Path, Bovington Tank Museum, Monkey World, Weymouth, Swanage.

5.0 out of 5 average rating, 103 reviews

Top guest favourite

A large window presents a stunning view of the beach and sea, illuminated by natural light. The light curtains gently frame the window, while a television stands on a dresser nearby. The serene coastal scenery offers a glimpse of a sandy beach and distant hills.

Apartment in Weymouth

Stunning Beachfront apartment overlooking the sea

A brand new apartment just 50 steps from the beach with free parking in the heart of Weymouth directly on the Esplanade with panoramic sea views of the award winning beach. Well equipped and nestled amongst shops and restaurants . Just minutes walk to bars , the harbour and train station. Fully fitted kitchen with family size fridge freezer, oven, microwave, toaster, kettle, cutlery, crockery, dishwasher, washing machine, flat screen TV's, Wifi, Hand, bath and beach towels provided.

4.92 out of 5 average rating, 524 reviews

Top guest favourite

A charming barn conversion features natural stone walls and large windows that invite ample sunlight. The surrounding landscape includes lush greenery and a clear blue sky, creating a serene rural atmosphere. The driveway leads to the entrance, providing easy access to the property.

Cottage in Dorset

Stunning Barn conversion +heated pool (15/5-15/9)

Courage Cottage is a two bedroom detached barn conversion in a Georgian farmyard.The barn was converted in 2013 so has all modern conveniences including underfloor heating. It is very individual and situated in a quiet , rural setting. It has two bedrooms with en-suite bathrooms. The village of Martinstown has an excellent pub and shop. Dorchester is 2 miles away and has every facility including good rail connections in all directions.Swimming pool (shared ) open May 15th-Sept 15th

4.8 out of 5 average rating, 207 reviews

Top guest favourite

A cozy sitting area features a plush olive green velvet sofa adorned with patterned and solid cushions. A stylish wooden chair complements the vintage aesthetic, while large artworks decorate the walls. Exposed wooden beams add character, and a patterned rug enhances the inviting ambiance.

Barn in Dorset

Arthouse - Curated artists’ studio + sauna

The former artists’ studio in a converted barn in Thomas Hardy’s West Dorset - close to Chesil Beach and the wonderful Jurassic Coast. The art-filled space, with tall ceilings and exposed beams, is curated with art, sculptures, and ceramics by the artist-owners. Mid-century furnishings complement hand-printed wallpaper and antique rugs. Doors open to a private courtyard garden with a patio and fire pit. The sauna, behind the main barn, overlooks a gravel garden.

5.0 out of 5 average rating, 139 reviews

Guest favourite

The exterior of the cottage features a charming stone façade with a thatched roof. A wooden door is surrounded by multiple windows. Lush greenery is present in the garden, along with a small patio area furnished with a dining set.

Cottage in Weymouth

Thatched Cottage by the Beach

The Stables is a charming thatched cottage nestled in the sort after village of Preston, Dorset. It is located a short walk to the beach and village amenities. It is perfectly located to access nearby famous Weymouth Beach, Weymouth Harbour and the beautiful Jurassic Coast. A romantic stable conversion with a recently re-designed Kitchen and Bathroom. It is perfect for an active summer beach holiday or a cozy winter holiday in front of the fire.

4.95 out of 5 average rating, 133 reviews

Top guest favourite

Cottage in Martinstown

Cosy, dog friendly cottage in the heart of Dorset

Take it easy at this unique and tranquil getaway in the heart of Dorset. Beautiful scenery is all around you in this cosy cottage. The Jurassic coastline a just a short drive away, as is the historic town of Dorchester. The village has a great local pub, and a shop selling local produce as well as some essential items. Enjoy the privacy of an entire home with a beautiful garden in picturesque surroundings.

4.87 out of 5 average rating, 205 reviews