Holiday rentals in Upwey

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.

The Garden Retreat

The Garden Retreat is a self contained dwelling, at the end of our garden. In a quiet residential area of Dorchester, in the summer there may be some noise from the surrounding gardens. Access from the road, leads directly to the Garden Retreat. We are in easy walking distance (about 10 minutes) from the centre of Dorchester. here you will find Cafes, restaurants and shops Dorchester is an historic town, with many place of interest. No Visitors. No smoking or vaping, on the premises. No pets.

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.

Artist’s Creative Hideaway & Sauna

Beautiful, inspiring, and peaceful, Arthouse is a place to escape. This converted art studio in West Dorset is close to Chesil Beach and the Jurassic Coast. It is surrounded by wildflowers and features contemporary art and sculptures by artists Rouwen and Reeve. The space is complemented by mid-century modern furnishings, high ceilings, and exposed beams. All doors open to a private patio and a naturalistic garden. The Sauna, located in the gravel garden looks out onto sculptures and plants.

Little Barn is a cosy dwelling in a remote valley

Little Barn is located in a remote valley between Upwey and Portesham near Weymouth in Dorset A converted Barn with a modern open plan interior. An adequate garden with Outdoor furniture and BBQ with an external secure store for bicycles etc. The area is good for walking (dogs welcome), many footpaths line the surrounding countryside. Hardy's monument is situated a few miles away. The area offers good cycling both on and off road. Good access to the Dorset coastline which is a short drive away.

The Bunker - a few minutes from the beach

You will be close to everything when you stay at this centrally-located stylish place. Dorset is breathtaking with its Jurassic coast, explore popular spots like Lulworth cove or the isle of Portland or stay put and enjoy all that Weymouth’s bustling town, harbour and beaches have to offer. It’s a short walk along the seafront to the town centre and the harbour side. With great seafood, and a wonderful selection of restaurants within walking distance you won’t be at a loss of places to eat.

Discover Little Drey: Your Perfect Getaway

At Little Drey, you'll find comfort, and warm hospitality, all while being conveniently close to Dorchester. A variety of restaurants, cafes, and shops are all within walking distance. Close to some of the best places to visit in Dorset, and within easy reach of famous beauty spots and amazing places to visit. Parking on property along with self-check-in, makes it super easy to have a relaxing, enjoyable break. Your host lives next door and is on hand to make your stay the best possible.

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.

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.

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.

Cheerful one bedroom home in the heart of Dorset

A great base for exploring Dorset and centrally-located. This newly decorated self contained 1 bedroom annexe has a fully equipped kitchen & in the county town of Dorchester, the birth place of Thomas Hardy. It is a perfect base to explore the beautiful countryside and Jurassic coast! The town’s amenities are only a short walk away including the new Brewery Square development. Complimentary tea and coffee also provided. Please note, we are unable to accommodate children

Flat One The Beaches

***Flat one the Beaches is in a central position & can be noisy in the evenings especially at the weekends***Recently converted Grade II listed building on Weymouth seafront. The apartment is one of four located off a private inner courtyard on the first floor. well equipped apartment across the road from Weymouth’s award winning beach and nestled a stones throw away from Weymouth town with its great choice of harbour side restaurants and bars.