Holiday rentals in Upwey

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Top-rated holiday rentals in Upwey

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Top 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
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.

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
5 out of 5 average rating, 113 reviews

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.

Guest favourite
Tiny home
4.92 out of 5 average rating, 277 reviews

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.

Superhost
A cozy living room is furnished with a spacious sectional sofa facing a wall-mounted TV. Large glass doors offer sweeping views of the sky and surrounding area. Green plants add a natural touch, while a sleek wood-burning stove creates a focal point in the inviting space.
Apartment
4.85 out of 5 average rating, 180 reviews

The Beach Hytte - Stunning Sea View Penthouse

Enjoy your perfect getaway in this award winning 2 bed penthouse apartment with 180 degree sea views in the heart of the tranquil Alum Chine area of Bournemouth just a few minutes walk from the beach. The property boasts two dining areas, one of which sits on the large balcony with views across Bournemouth beach and a bespoke wood burning stove for the winter nights. The open plan kitchen leads onto a cozy living room where you can enjoy Sky Glass TV entertainment through super fast WiFi.

Top guest favourite
A well-lit living area is shown, featuring a light green wall and a comfortable sofa positioned near a window. A small wooden table with two chairs is visible, alongside a decorative round rug on the floor. A bedside lamp and a wall-mounted shelf complete the space.
Home
4.97 out of 5 average rating, 109 reviews

Guest Suite in Martinstown

Recently converted guest suite in a house situated in the middle of a picturesque village in Dorset. Private access through your own front door and set aside from the main house to ensure privacy. Private area outside for your use or you are welcome to explore the extensive gardens and woodland. Cooking facilities are limited but fridge, microwave, electric hob, toaster and kettle are supplied. Good food is served in the village pub a short stroll away. Dorchester town is a 10 minute drive.

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
4.79 out of 5 average rating, 194 reviews

Stunning Barn conversion with heated swimming pool

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

Guest favourite
A private garden features a round table surrounded by four chairs, set on a stone patio. Lush greenery and flowering plants border a well-maintained lawn, while a rustic shed is visible in the background under a clear blue sky dotted with clouds.
Cottage
4.94 out of 5 average rating, 305 reviews

Jasmine Cottage

Jasmine Cottage is a characterful, compact barn conversion, that sits next to the 400 year old farm house. It sleeps up to four people (including infants), with a double and a twin room. We are one mile away from The Wise Man Inn - an award-winning pub; 6 miles from Dorset's stunning Jurassic coast and 3 miles from the county town of Dorchester. You will, however, need a car- or bikes! Sorry, no pets and no smoking. No EV charging, yet, but there are many fast charging points nearby.

Top guest favourite
A bright living room is illuminated by natural light from a large window, offering views of green fields. Comfortable seating is arranged around a wooden coffee table, with plush sofas and a decorative plant enhancing the welcoming space. A television set is positioned against the wall.
Bungalow
4.94 out of 5 average rating, 114 reviews

Bay View Luxury Stays - Southdown

This beautiful four bedroom property is located in the picturesque seaside town of Weymouth, offering breathtaking views over a stunning nature reserve , with its spacious rooms, comfortable furnishings and modern amenities, this property provides the perfect home away from home for families and friends, take in the sea air from the spacious garden patio area or admire the view from the many windows, the property is a short walk from the beach and charming shops.

Top 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
4.96 out of 5 average rating, 108 reviews

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.

Top guest favourite
Cottage
4.87 out of 5 average rating, 179 reviews

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.

Top guest favourite
A spacious patio area features a circular dining table surrounded by six chairs, complemented by a large umbrella. Decorative planters with green plants add a touch of nature. Full height glass doors provide a view of the surroundings while inviting natural light.
Flat
5 out of 5 average rating, 526 reviews

Apartment with panoramic sea views

We are situated 600 yards, through the nature reserve, from the beach and at the top of the hill with panoramic views over Weymouth bay, beach and nature reserve. 3 miles from the town With loads of parking available outside .You’ll love my place because of the location, the views. good for couples, solo adventurers, business travellers and small, well behaved dogs.

Guest favourite
An aerial view captures Bellamont House surrounded by rolling hills and vibrant autumn foliage. The light of dawn casts a warm glow over the property, emphasizing its spacious layout and serene setting within the Bride Valley landscape.
Flat
4.96 out of 5 average rating, 130 reviews

Elegant Wing of a Country House - Bride Valley

The West Wing is a beautiful self contained apartment of Bellamont House. It benefits from a smart, light and spacious atmosphere. It is well equipped with all the comforts of home. Bellamont is situated in the picturesque Bride Valley, a Designated Area of Outstanding Natural Beauty & is only 5 miles from the sea & the stunning World Heritage Jurassic Coast.

Popular amenities for Upwey holiday rentals

  1. Airbnb
  2. United Kingdom
  3. England
  4. Dorset
  5. Upwey