Photo by Sue Wormald

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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare Vacation Homes in Upwey with updated reviews, rates, and availability.

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Terrace/patio

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

10.0 out of 10, Exceptional, (44)
"The views are amazing. Walking path and the sea right behind house. View after view. Well equipped kitchen with tons of space, comfy living room- and I loved the sunroom out back! This was October weather with occasional rain and wind. Must be truly amazing in summer with outdoor spaces.. convenient for Dorset exploring."
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Quiet location, short walk to beach, with views of Portland and Jurassic coast
Beach nearby, sun loungers

Quiet location, short walk to beach, with views of Portland and Jurassic coast

9.8 out of 10, Exceptional, (90)
"The location was great for the sailing, the house met all expectations - clean, good facilities, well kitted out. "
Quiet location, short walk to beach, with views of Portland and Jurassic coast
Beautiful large Georgian house with a big garden. Perfect for a family or two!
Outdoor dining

Beautiful large Georgian house with a big garden. Perfect for a family or two!

10.0 out of 10, Exceptional, (69)
"We have had an amazing weekend at this beautiful property which is spacious, comfortable, quirky and full of home comforts. Everything you need is here and Wareham was a delight…we had fun in Wareham pottery painting at Pottery Corner and an amazing meal at The Italian Kitchen. Thank you so much. "
Beautiful large Georgian house with a big garden. Perfect for a family or two!
A contemporary house close to the town centre with fantastic views over Radipole Lake.
Exterior

A contemporary house close to the town centre with fantastic views over Radipole Lake.

9.6 out of 10, Exceptional, (14)
"Good comfortable house conveniently situated close to town, beach and all local facilities. "
A contemporary house close to the town centre with fantastic views over Radipole Lake.
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset
Property grounds

Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset

9.8 out of 10, Exceptional, (52)
"Set in isolated rural village with lovely views and walks. Our vist was marred by horrendous wet weather,but we made the best of it. Mark and Madeline were lovely people who made us welcome and dealt with any issues and gave advice about the area."
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset
Barn conversion, quiet location and heated swimming pool ( from mid May)
Exterior

Barn conversion, quiet location and heated swimming pool ( from mid May)

9.4 out of 10, Exceptional, (59)
"Fantastic property. Great location. Clean, with all the necessary facilities and utilities."
Barn conversion, quiet location and heated swimming pool ( from mid May)
Stable Conversion Near Lulworth Cove/Jurassic Coast
Beach nearby, sun loungers

Stable Conversion Near Lulworth Cove/Jurassic Coast

10.0 out of 10, Exceptional, (106)
"We had a lovely time on our stay in this cosy and beautifully clean property all was as described, and the milk, tea and cookies were a lovely touch. The booking in process was really easy and Paul was a good host. The garden is nicely kept and a paradise if you like birdwatching and the beautiful local surrounding area makes this a wonderful place to stay. We would definately recommend"
Stable Conversion Near Lulworth Cove/Jurassic Coast
Cosy Dorset Cottage Just for Couples near Lyme Regis
Miscellaneous

Cosy Dorset Cottage Just for Couples near Lyme Regis

8.0 out of 10, Very Good, (2)
"Just got back from a great stay at Lyme Barn. Property is spot on for a couple, great access to the best spots on the Jurassic Coast. Ruthie (out host) was lovely- brilliant to communicate with and that makes all the difference. Location is close to the A35 so some road noise which we knew about beforehand and didn't bother us a bit. Looking forward to coming back."
Cosy Dorset Cottage Just for Couples near Lyme Regis
Host & Stay | Clearmount Cottage
Outdoor dining

Host & Stay | Clearmount Cottage

10.0 out of 10, Exceptional, (3)
"What a beautiful property tucked away in a fantastic location. The gardens were equally as enjoyable as the house and we were lucky with the sunshine.Great access to Castle Cove beach, Sandsfoot Castle gardens, and the Rodwell Trail, all within a 5 minute walk.Thank you, we will definitely be back."
Host & Stay | Clearmount Cottage
Historical, Characterful, Converted Old School House
Exterior

Historical, Characterful, Converted Old School House

9.0 out of 10, Wonderful, (2)
"Very nice clean well furnished"
Historical, Characterful, Converted Old School House
The Victorian Barn self catering holidays with pool & hot tubs
Superior House, 4 Bedrooms, Hot Tub, Garden View | Egyptian cotton sheets, premium bedding, memory foam beds

The Victorian Barn self catering holidays with pool & hot tubs

4.0 star property
9.4 out of 10, Exceptional, (3)
"A lovely venue for a few days R&R in this part of Dorset. The accommodation is modern, spacious and of good quality, with great on-site facilities (pool, sauna, etc). Recommended."
The Victorian Barn self catering holidays with pool & hot tubs
Beautiful, family friendly Cottage with sea views of Chesil Beach
Exterior

Beautiful, family friendly Cottage with sea views of Chesil Beach

9.6 out of 10, Exceptional, (17)
"The property was a beautifully quaint cottage very clean and had everything we needed. Definitely recommend it."
Beautiful, family friendly Cottage with sea views of Chesil Beach
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Fridge, microwave, oven, stovetop

Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)

9.8 out of 10, Exceptional, (34)
"Excellent family house for celebrating a70th and 40th birthdays . The owners were very generous with the heating. "
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Eleven Upway Street
Beach

Eleven Upway Street

Eleven Upway Street
Private detached cottage to rent on Chesil Beach
Dining

Private detached cottage to rent on Chesil Beach

10.0 out of 10, Exceptional, (63)
"Stunning location. The house was perfect for a proper break away from it all. Walks, beach fishing and plenty of places to visit nearby."
Private detached cottage to rent on Chesil Beach
A charming seaside cottage 5 minutes walk from beach on Jurassic Coast
Terrace/patio

A charming seaside cottage 5 minutes walk from beach on Jurassic Coast

9.4 out of 10, Exceptional, (33)
"Very good property, it suited all of our needs"
A charming seaside cottage 5 minutes walk from beach on Jurassic Coast
The Cartshed
Property grounds

The Cartshed

10.0 out of 10, Exceptional, (4)
"Beautiful old conversation not overdone hot tub was great! Just an overnight stay but would go again. Just one small gripe, the mezzanine bed area needs proper steps as it was painful on bare feet, but it would not prevent us from coming back again."
The Cartshed
Ammonite barn conversion in stunning location
Aerial view

Ammonite barn conversion in stunning location

10.0 out of 10, Exceptional, (16)
"The views are something else, an amazing location and excellent accommodation in area of outstanding beauty. Lived in East Dorset for many years, but West Dorset and coast line is just something. "
Ammonite barn conversion in stunning location
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
Exterior

Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

9.0 out of 10, Wonderful, (42)
"Very nice and i will stay again"
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
Cosy Country & Coastal Barn Retreat for Couples in Dorset
Beach

Cosy Country & Coastal Barn Retreat for Couples in Dorset

10.0 out of 10, Exceptional, (2)
"We had a lovely stay at this property, privacy and peace, which was just what we were looking for, only sorry that we couldn't stay longer! The cottage was excellent, with everything you need for a short stay, and very well equipped. There was fresh bread, milk, jam, Lurpak (my preference), and even some locally made biscuits, which were lovely, all provided by our Host Ruth, thank you Ruth. We will be booking again!"
Cosy Country & Coastal Barn Retreat for Couples in Dorset
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Upwey

The Dorset Resort
Signature Chalet, 3 Bedrooms, Accessible, Sauna | Desk, laptop workspace, blackout drapes, iron/ironing board

The Dorset Resort

4.0 star property
10.0 out of 10, Exceptional, (28)
"The property was clean. Just the beds were single Beds in all couple rooms. Would be great if they had double beds instead. "
The Dorset Resort
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
Exterior detail

Self Contained Garden Studio With Private Decked Terrace, close to town and sea

9.6 out of 10, Exceptional, (125)
"Brilliant stay as before. Fantastic, welcoming hosts and beautiful comfortable accommodation "
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
Beautiful, family friendly Cottage with sea views of Chesil Beach
Exterior

Beautiful, family friendly Cottage with sea views of Chesil Beach

9.6 out of 10, Exceptional, (17)
"The property was a beautifully quaint cottage very clean and had everything we needed. Definitely recommend it."
Beautiful, family friendly Cottage with sea views of Chesil Beach
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.