Vacation rentals in Upwey

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Top-rated vacation rentals in Upwey

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Top guest favorite

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.

Condo in Dorset

4.98 out of 5 average rating, 106 reviews

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.

Guest favorite

A dining area features a round table surrounded by a combination of blue and gray chairs. Natural light filters through large, curved windows adorned with blinds. A plant adds a touch of greenery, while a decorative map of Dorset is displayed on the wall.

Condo in Overcombe

4.97 out of 5 average rating, 115 reviews

No1 By The Sea - Modern Apt, 5mins walk from beach

Welcome to 'No1 By The Sea', a modern spacious 2 bdrm luxury ground floor apartment with car parking, just a short stroll away to a gorgeous beach where you can enjoy the local beach cafe/restaurant. A great choice for the water sport enthusiasts, a wonderful location for all. Take a walk along the esplanade to Weymouth town centre to the award winning golden sands & visit the gorgeous harbour where there are abundance of restaurants. A great spot to explore the beautiful jurassic coast line.

Guest favorite

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 Dorset

4.92 out of 5 average rating, 195 reviews

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.

Guest favorite

The exterior view of the converted barn is presented, showcasing the stone structure surrounded by lush greenery. A gravel driveway leads to the property, with an outdoor seating area visible. Neat hedges outline the garden, offering a sense of privacy amid the scenic countryside.

Cottage in Dorset

4.95 out of 5 average rating, 256 reviews

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.

Top guest favorite

A spacious sleeping area features a cozy king-size bed adorned with decorative pillows. Large windows allow natural light to fill the room, complemented by light hardwood flooring. A small dining table with chairs is positioned nearby, enhancing the inviting atmosphere.

Guest suite in Dorset

4.92 out of 5 average rating, 240 reviews

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.

Guest favorite

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

4.97 out of 5 average rating, 102 reviews

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.

Guest favorite

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.

Condo in Weymouth

4.92 out of 5 average rating, 449 reviews

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.

Guest favorite

A cozy sleeping area features a spacious bed with soft gray bedding and a decorative throw pillow. A wooden bookshelf displays various items, while a glass door opens to a view of the outside. Warm lighting highlights the room's inviting design.

Farm stay in Osmington

4.93 out of 5 average rating, 270 reviews

Beautiful Annex situated on the Jurrasic Coast.

Pixon Barn is situated on a working farm on the Jurassic Coastline within an easy driving distance to Weymouth, Lulworth Cove, and Abbotsbury. It is located next to numerous bridlepaths, perfect for avid walkers, cyclists and lovers of the countryside. We welcome any and all well behaved dogs. There are several pubs all within a 5 minutes distance by car, as well as our own farm cafe and shop located on the main road into Weymouth. Best ice-cream around.!

Top guest favorite

An indoor swimming pool is featured, surrounded by large windows allowing natural light. The ceiling beams reveal a spacious, airy atmosphere. Two red chairs are positioned nearby, and a shallow end is visible with steps leading into the water. A blue cover rests along one side of the pool.

Cottage in Dorset

4.98 out of 5 average rating, 368 reviews

The Condo (Indoor Pool available May- end Sept)

Self contained detached cottage in a tranquil location close to the famous 'Jurassic Coast' ; Durdle Door, Lulworth, Corfe Castle, Weymouth and Dorchester are all a short drive away. Further attractions close by are Monkey World, Bovington Tank Museum, and Sculpture by the lakes. There is a well stocked village shop and good village pub. Dorset has so much to offer, with beautiful coastline and breathtaking scenery. Relax in the pool at your leisure!

Guest favorite

A view of a charming seafront street, lined with historic buildings in various hues. Pedestrian-friendly spaces are visible, with outdoor seating outside restaurants. The well-maintained promenade leads towards the beach, highlighting the vibrant coastal atmosphere of Weymouth.

Apartment in Weymouth

4.9 out of 5 average rating, 437 reviews

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.

Top guest favorite

The contemporary cabin features a clean, modern exterior with a dark blue façade and a spacious front deck. Stone steps lead to the entrance, surrounded by well-maintained lawn and greenery, creating a welcoming outdoor space.

Cabin in Dorset

5 out of 5 average rating, 113 reviews

Luxury contemporary cabin in the village of Upwey.

Luxury hand built contemporary cabin kitted out with bespoke fittings in a rural setting conveniently nestled between the seaside town of Weymouth & Dorsets' county town of Dorchester in the beautiful village of Upwey. Private access road leads to secluded cabin which is set in approx 1/2 acre surrounded by trees. Plenty of free parking directly outside. Please note there is a 3 night minimum stay. Hot tub has now been added for 2021!

Top guest favorite

A tall stone monument is prominently situated atop a grassy hill, surrounded by lush greenery. A weathered wooden signpost stands in the foreground, pointing in two directions. The sky features scattered clouds and clear blue sections, creating a bright outdoor scene.

Home in Dorset

4.97 out of 5 average rating, 144 reviews

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.