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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 263 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, (45)
"The hosts have gone out of their way to make their house an inviting place to stay in. The location is superb and made our relaxation times at home just as nice as our exploration of Dorset. Lots of lovely places to visit. Highly recommend this as a holiday venue."
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
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, (55)
"Thoroughly enjoyed our stay in this well equipped accommodation in a a lovely rural setting."
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset
Sea-Esta – A Stylish Coastal Retreat in the Heart of Weymouth
Iron/ironing board, travel crib, WiFi, bed sheets

Sea-Esta – A Stylish Coastal Retreat in the Heart of Weymouth

Sea-Esta – A Stylish Coastal Retreat in the Heart of Weymouth
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, (70)
"Big house more then fully equipped and a very nice yard, walking distance to everything in town."
Beautiful large Georgian house with a big garden. Perfect for a family or two!
Farm House in stunning Dorset countryside with Hardy views
Exterior

Farm House in stunning Dorset countryside with Hardy views

10.0 out of 10, Exceptional, (1)
"Great comms and lovely welcome from Luba and Chris for our two night stay. Easy to find and parking right next to the front door. The cottage was spotlessly clean and very peaceful with two spacious doubles, both with their own TV and modern en-suite facilities. Comfortable lounge with wood burner, TV and jigsaw ready to go - all with lovely views over to Hardy's Monument. Ideal location for visiting the local area by car - we went to Weymouth (Catch! restaurant was fab), Dorchester, Poundbury,...
The price is AED 554
AED 633 total
includes taxes & fees
1 Jun - 2 Jun
Farm House in stunning Dorset countryside with Hardy views
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.

9.4 out of 10, Exceptional, (15)
"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.
The Old Chapel - Exclusive Retreat
Living area

The Old Chapel - Exclusive Retreat

9.0 out of 10, Wonderful, (2)
"Beautiful place."
The Old Chapel - Exclusive Retreat
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)
The Victorian Barn self catering holidays with pool & hot tubs
Quiet location, short walk to beach, with views of Portland and Jurassic coast
Beach nearby

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

10.0 out of 10, Exceptional, (95)
"It was very clean and all the things there that was needed wih loverly views and surrounding area .i would recommend the stay there."
Quiet location, short walk to beach, with views of Portland and Jurassic coast
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
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, (19)
"Had a lovely time good central location. Nice place to stay better than a B&B"
Beautiful, family friendly Cottage with sea views of Chesil Beach
Independent Garden Wing of Dorset country house
Exterior

Independent Garden Wing of Dorset country house

10.0 out of 10, Exceptional, (1)
"Smedmore is the most incredible house and it is a joy to spend time there in the garden cottage. We had four fantastic days there running around and exploring the area. The children loved it - it is so peaceful and you feel as if you've come to a real haven. The team who run Smedmore are friendly, kind and very responsive. We would go back and back."
Independent Garden Wing of Dorset country house
Luxury coastal property with private indoor pool.
Interior

Luxury coastal property with private indoor pool.

10.0 out of 10, Exceptional, (7)
"The property is done up to a really high standard and was ideal for our group. Great Facilities, kids had a blast Location is fabulous"
Luxury coastal property with private indoor pool.
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, (35)
"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)
Sunny Barn Stay, Hot Tub & Rural Views – Leopold at The Victorian Barn Dorset
Outdoor dining

Sunny Barn Stay, Hot Tub & Rural Views – Leopold at The Victorian Barn Dorset

10.0 out of 10, Exceptional, (2)
"Lovely location, beautiful and spacious cottage! thank you"
Sunny Barn Stay, Hot Tub & Rural Views – Leopold at The Victorian Barn Dorset
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Aerial view

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

The price is AED 1,236
AED 1,330 total
includes taxes & fees
6 Jun - 7 Jun
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Private detached cottage to rent on Chesil Beach
Dining

Private detached cottage to rent on Chesil Beach

10.0 out of 10, Exceptional, (66)
"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
Lakeside retreat with hot tub, games room and on-site spa and pool
Property grounds

Lakeside retreat with hot tub, games room and on-site spa and pool

Lakeside retreat with hot tub, games room and on-site spa and pool
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
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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