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Compare 219 Vacation Homes in Portland with updated reviews, rates, and availability.

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

10.0 out of 10, Exceptional, (44)
"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

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

10.0 out of 10, Exceptional, (91)
"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

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

10.0 out of 10, Exceptional, (69)
"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 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.

Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight

9.4 out of 10, Exceptional, (63)
"The cottage was as described. It had everything you could ever need. Beds were very comfortable. The view from the cottage was fantastic!! "
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight

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

10.0 out of 10, Exceptional, (106)
"A lovely property and hosts. Excellent accommodation and beautiful garden. Great for visiting Arne, Brownsea Island, Swanage, Wareham and Dorchester. Can't recommend it enough!"
Stable Conversion Near Lulworth Cove/Jurassic Coast

Host & Stay | Clearmount Cottage

10.0 out of 10, Exceptional, (3)
"Amazing"
Host & Stay | Clearmount Cottage

Historical, Characterful, Converted Old School House

9.0 out of 10, Wonderful, (2)
"Very nice clean well furnished"
Historical, Characterful, Converted Old School House

Beautiful, family friendly Cottage with sea views of Chesil Beach

9.6 out of 10, Exceptional, (17)
"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

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

9.8 out of 10, Exceptional, (34)
"Our entire family stayed here to celebrate a special birthday. We were very pleased with the farmhouse and the amount of space. The hosts were very pleasant and helpful. Kitchen was well equipped. Only reason we gave a 4 for cleanliness is because it was a little dusty (But expected due to it being a farmhouse!) Would recommend to all. "
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)

Eleven Upway Street

Eleven Upway Street

Private detached cottage to rent on Chesil Beach

10.0 out of 10, Exceptional, (63)
"The location, the house, wow this was absolutely faultless. 7 adults, 1 teenager and 2 two dogs for 3 nights at new year and it was everything we hoped for. Spectacular views and perfect for the storm as we hunkered down and had a fire in the comfortable lounge playing games. We all found the beds extremely comfortable and each bathroom was spacious and very clean. The whole place, just incredible!"
Private detached cottage to rent on Chesil Beach

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

Spacious Coastal House with Stunning Sea Views N Near Sea & Sandy Beaches

10.0 out of 10, Exceptional, (88)
"Lovely holiday house in great location ideal for our needs. Would recommend."
Spacious Coastal House with Stunning Sea Views N Near Sea & Sandy Beaches

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

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

Pebble House - Sea views, parking, family friendly

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay in Pebble House. It is comfortable and well equipped. Most of all we liked the view over Weymouth bay."
Pebble House - Sea views, parking, family friendly

4 Bed 4 bath 4 star family town house 80 yds to beach, sky & wifi Recent refurb

9.2 out of 10, Wonderful, (40)
"The property was booked for a fishing party for three days so was really just a Bed for the nights as we were out most of the time. It was well positioned in the centre of Weymouth with two parking permits available for the immediate area (not always easy to find a spot). The property was totally fine for our requirements with several showers albeit they were a bit erratic when more than one were in use). Would book again."
4 Bed 4 bath 4 star family town house 80 yds to beach, sky & wifi Recent refurb

5 bed, 5 bath, Slps 18, Town Ho. 60 yds Weymth beach & harbour, NEWLY RENOVATED!

9.6 out of 10, Exceptional, (7)
"An amazing location for a big family get together. The house has everything you need and more. We would all definitely stay here again. Amazing value for money"
5 bed, 5 bath, Slps 18, Town Ho. 60 yds Weymth beach & harbour, NEWLY RENOVATED!
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 Portland

Beautiful, family friendly Cottage with sea views of Chesil Beach

9.6 out of 10, Exceptional, (17)
"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

The Dorset Resort

4.0 star property
10.0 out of 10, Exceptional, (28)
"I have stayed here a few times, never been disappointed and will always come back for another visit."
The Dorset Resort

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

9.6 out of 10, Exceptional, (126)
"FELT VERY RELAXED PROPERTY EVERY YOU WANT"
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
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.