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Top Holiday Rentals in Upwey

40 The Ridgeway

3.5 star property
The price is £406
includes taxes & fees
7 Aug - 8 Aug
40 The Ridgeway

Luxury Pine Wood Lodge, situated in beautiful Dorset Countryside,attractions nr

9.2 out of 10, Wonderful, (87)
"Great location for a peaceful family stay. beautiful surroundings."
Luxury Pine Wood Lodge, situated in beautiful Dorset Countryside,attractions nr

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

10.0 out of 10, Exceptional, (99)
"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

The Victorian Barn self catering holidays with pool & hot tubs

4.0 star property
9.0 out of 10, Wonderful, (4)
"We stayed in Helena, it was very clean and well equipped. Concern about escape routes in the event of a fire. Some rooms didn’t have a large enough window to get out of. Swimming pool great, as was the hot tub. Lovely setting near Blandford. Would recommend getting shopping delivered as quite remote. "
The Victorian Barn self catering holidays with pool & hot tubs

Dorchester Nook

10.0 out of 10, Exceptional, (1)
"Good sized en suite room in private flat. Powerful shower, good wifi. Convenient for Dorchester centre, no parking but public (paid) car park just across the road. There is a cat. Comfortable bed and very quiet location even though close to centre"
The price is £99
includes taxes & fees
3 Aug - 4 Aug
Dorchester Nook

The Dorset Resort

4.0 star property
10.0 out of 10, Exceptional, (36)
"Amazing properties set in a beautiful tranquil setting. Wildlife everywhere and great for children to be outdoors, lovely walks and grounds. "
The Dorset Resort

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

9.6 out of 10, Exceptional, (137)
"Paul & Julia are great hosts and are so welcoming. We had a lovely stay in the property, it was great for the 2 of us and our dog. Easy walk to shops and a short drive to the beach. Would highly recommend a stay here."
Self Contained Garden Studio With Private Decked Terrace, close to town and sea

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

10.0 out of 10, Exceptional, (47)
"An excellent property in a great location."
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

Apartment with stunning Sea View

9.4 out of 10, Exceptional, (55)
"Great location, amazing view."
Apartment with stunning Sea View

Apartment near the beach with private parking and pet friendly

9.4 out of 10, Exceptional, (24)
"Couldn't as for more, clean, lovely little property about 10 mins from the beach and town center."
Apartment near the beach with private parking and pet friendly

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

10.0 out of 10, Exceptional, (71)
"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!

A beautiful comfortable cottage in the centre of Bridport.

A beautiful comfortable cottage in the centre of Bridport.

Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town

10.0 out of 10, Exceptional, (52)
"Quiet, peaceful location with amenities close to hand just the place for a relaxing week. Property is very well equipped and the secluded garden at the back a bonus."
Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town

Cosy Peacehaven. Free on site Parking! Pet friendly!

10.0 out of 10, Exceptional, (1)
"Beautifully decorated little apartment. Perfect for exploring Weymouth and the surrounding area. We had a lovely little break. "
The price is £156
includes taxes & fees
31 Aug - 1 Sept
Cosy Peacehaven. Free on site Parking! Pet friendly!

Beautiful, family friendly Cottage with sea views of Chesil Beach

9.6 out of 10, Exceptional, (20)
"Great little cottage, within walking distance of the beach. Great host "
Beautiful, family friendly Cottage with sea views of Chesil Beach

Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset

9.8 out of 10, Exceptional, (83)
"Pleased with the accommodation overall, beautiful garden and view over countryside, cottage well equipped, and great local walks nearby"
Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset

Luxury Apartment close to shops, coast and beautiful beaches. Far reaching views

10.0 out of 10, Exceptional, (70)
"Beautiful and comfortable apartment. Would definitely recommend."
Luxury Apartment close to shops, coast and beautiful beaches. Far reaching views

Ocean Retreat by Wessex Quarters

6.0 out of 10, (1)
"The property is spacious for two people; however, it was not properly cleaned when we arrived. Under the sink was a leak or something, and there were cobwebs in the kitchen area. The trays in the oven are full of oil, so when you're trying to cook something in the oven, the kitchen is full of that smell, and the cooker hood would not even get the smell out. The bed was uncomfortable, and the sofa in the living area was not good either. The entrance is from the road just in front of the bus stop,...
Ocean Retreat by Wessex Quarters

Beachside, stunning apartment with sea and harbour views

9.6 out of 10, Exceptional, (65)
"This apartment was amazing ,very clean and equip with everything you needed. I would definitely stay here again. "
Beachside, stunning apartment with sea and harbour views

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 £172
includes taxes & fees
25 Aug - 26 Aug
Farm House in stunning Dorset countryside with Hardy views
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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Top Upwey Hotel Reviews

Frequently asked questions

Can I find a holiday rental in Upwey?

Yes, there are holiday rentals close to the most popular sights in Upwey, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Upwey has to offer?

The Victorian Barn self catering holidays with pool & hot tubs: This holiday home rental outside of Upwey is located in a rural location, and has an indoor pool, a patio and free WiFi to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher and a stovetop. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Upwey?

Choose from 3 Expedia holiday rentals in Upwey for a memorable holiday.

What’s there to see and do in Upwey?

While exploring the area, visit family-friendly sights like SEA LIFE Centre Weymouth, or get outside and enjoy nature at Dorset Area of Outstanding Natural Beauty. In the wider area, you’ll find Durdle Door and Bowleaze Cove Beach.

What’s a holiday rental in Upwey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Upwey. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.