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Compare 204 Vacation Homes in Portland with updated reviews, rates, and availability.

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!

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!

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

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

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

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)

Host & Stay | Clearmount Cottage

10.0 out of 10, Exceptional, (2)
"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)
"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)

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)

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

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

Eleven Upway Street

Eleven Upway Street

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

10.0 out of 10, Exceptional, (88)
"A group of 9 friends stayed at this great house for 4 nights over New Year. Fantastic location with amazing views. The communication with the owner was excellent. More than adequate facilities for our needs with lots of information about the house etc. We all had a great time and would highly recommend."
Spacious Coastal House with Stunning Sea Views N Near Sea & Sandy Beaches

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

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

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!

2 bed comfy house

10.0 out of 10, Exceptional, (9)
"We had a wonderful 2 night stay. The place was immaculate and spotlessly clean, there was everything we needed and the location was excellent for Wareham and also nearby Monkey world which was the main reason for our trip. We would definitely stay again."
2 bed comfy house

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.
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)
"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

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

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
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.