Vacation rentals in Upwey

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.

The Old School House Annexe

Our Annexe is a peaceful and quiet space situated in the semi rural area of Upwey in Weymouth. It is the perfect spot to recharge your batteries, it is fully equipped, clean and comfortable. We have an inside Entertainment area which guests are welcome to use with a hot tub, tv and darts board and comfortable seating for chilling. There is also a Woodburner oven for guests use. Fantastic local walks on the doorstep and good local amenities with Weymouth town, beach and shops 10 mins drive.

Palm Cottage

A good sized modern One bedroom garden annex only a short walking distance to local pub, take away, convenience store & hairdressers with a 20 minute walk into the Town Centre and Beach (£6 - £7 taxi ride) Weymouth is a very popular tourist attraction with numerous high end eating establishments, a superb beach and harbour which are particularly vibrant during the Spring and Summer months, a golf course and a railway station. Only 13 miles from the picturesque Lulworth Cove & Durdle Door

The Old Reading Room West Stafford

The Victorian Reading Room of West Stafford is of historical importance. Used before the war as a Reading Room for the villagers and estate workers, the newspapers were provided, the village shop in the late 1930s, then a workshop and a store room for the church. We have now lovingly restored, decorated and furnished this amazing building into a cosy self catering holiday retreat, "far from the madding crowd" Open plan, comfy double sofabed, wood burner, country walks and fabulous village pub.

The Hide with Private Wood Fired Hot Tub option

'The Hide' is a truly romantic hideaway on an English Vineyard with your own Shepherd's Hut, Cabin, Shower Room & Private Wood Fired Hot Tub for two - there is a £50 fee for the wood fired hot tub Please be aware the Airbnb Guest Service Fee of 12.5% is now included in our prices Everything you see in the photos are for your own exclusive use Enjoy beautiful sunsets over the vines whilst soaking in your own private wood fired hot tub A perfect place to relax in a romantic setting for two

Cosy private Loft overlooking Dorset countryside

Nestled in the heart of the Dorset countryside, The Loft is your ideal 'getaway'. From stunning views to a comfy king-size bed, this cosy space will provide you with everything you need to relax. Open the stable door, and listen to the birds, reconnect with nature while sipping coffee and tucking into a selection of breakfast options provided upon your arrival. With an abundance of local amenities, please see the guide for my favourite secret spots! We look forward to welcoming you!

Jurassic Coast Boutique Retreat with Views

Set amid the rolling Dorset countryside with far reaching breathtaking views The Hayloft is a relaxed luxury retreat designed for slow, restorative stays. Part of Grandview Farm The Hayloft is a self contained annex offering a secluded, peaceful haven just moments from the Jurassic Coast. Thoughtfully styled with natural textures and luxurious touches throughout, it is the perfect base for a couple or two friends who enjoy coastal walks, cosy mornings and drinks under the stars.

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.

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.

Seaside, Countryside, Lower Butchers Cottage

Kick back and relax in this calm, stylish space. Lower Butchers Cottage really is the best of both worlds, located on the outskirts of Weymouth in the picturesque village of Upwey. The seafront is approx 3 miles away and we are on the main bus route from Dorchester to Weymouth, child & dog friendly, Ideal for the beach, Jurassic Coast walks and more, close to Upwey train station

Sunny gardens near beach, with countryside views

Cosy cottage near beach with two sunny gardens. Lovely views over Dorset countryside, close to Weymouth town centre. Private car parking space infront of house for two cars. Peaceful setting to relax. Sleeps 4 people - 1 double bedroom and 1 twin room. Downstairs - open plan sitting and dining room. New well equipped kitchen. Shower room. Excellent WIFI provided.

The Old Chapel - Exclusive Retreat

The Old Chapel dates from 1809, a converted Methodist chapel and listed Grade II as of architectural or historic interest. An easily recognisable property, set amongst pretty stone cottages that run along the river 'Wey' through the picturesque village of Upwey, just a short drive from the popular seaside town of Weymouth.