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Compare 170 Vacation Homes in Portland with updated reviews, rates, and availability.

Private detached cottage to rent on Chesil Beach
Exterior

Private detached cottage to rent on Chesil Beach

10.0 out of 10, Exceptional, (61)
"Back to Greenbanks to get our annual fix. Fab house, fab location, total isolation away from it all."
Private detached cottage to rent on Chesil Beach
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Exterior detail

Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast

9.8 out of 10, Exceptional, (89)
"It was very clean and all the things there that was needed wih loverly views and surrounding area .i would recommend the stay there."
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
Bedroom 3

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
Historical, Characterful, Converted Old School House
Interior

Historical, Characterful, Converted Old School House

9.0 out of 10, Wonderful, (2)
"Very nice clean well furnished"
Historical, Characterful, Converted Old School House
Host & Stay | Clearmount Cottage
Clearmount Cottage, Weymouth - Host & Stay

Host & Stay | Clearmount Cottage

Host & Stay | Clearmount Cottage
Luxury Detached House and Grounds, also benefits from full disabled facilities.
Property grounds

Luxury Detached House and Grounds, also benefits from full disabled facilities.

9.4 out of 10, Exceptional, (73)
"We absolutely love this gorgeous house. It's really well kitted out, it's clean, it's in a beautiful place and it's so so quiet. We all slept like logs and had a wonderful relaxing time. Thank you so much again."
Luxury Detached House and Grounds, also benefits from full disabled facilities.
Beautiful, family friendly Cottage with sea views of Chesil Beach
Room

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
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Views over the valley from bedroom

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

9.6 out of 10, Exceptional, (61)
"Well equipped house, great views no complaints except single track down to cottage overgrown with brambles , needs a bit of a trim. Overall pleased all round "
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
wonderful view from first floor veranda

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
Spacious Coastal House with Stunning Sea Views N Near Sea & Sandy Beaches
STUNNING DETACHED HOUSE WITH INCREDIBLE SEA VEWS NEAR SUPERB BEACHES

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

10.0 out of 10, Exceptional, (86)
"The property was very clean and welcoming with lots of thoughtful touches. We had a fantastic time and will definitely go back. Sarah "
Spacious Coastal House with Stunning Sea Views N Near Sea & Sandy Beaches
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Room

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

9.8 out of 10, Exceptional, (32)
"The property was large and comfortable for our party of 10, with a well equiped kitchen, BBQ area and games room. The location js stunning, with great views."
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Barn conversion, quiet location and heated swimming pool ( from mid May)

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)
Historical Jurassic Coastline and small fishing harbour
Room

Historical Jurassic Coastline and small fishing harbour

9.6 out of 10, Exceptional, (21)
"Only stayed one night out of seven Hosts agreed refund VRBO not so accommodating"
Historical Jurassic Coastline and small fishing harbour
Eleven Upway Street
Room

Eleven Upway Street

Eleven Upway Street
Beautiful Dorset Country House in the Heart of the Stunning Isle of Purbeck
Broadmead

Beautiful Dorset Country House in the Heart of the Stunning Isle of Purbeck

9.4 out of 10, Exceptional, (9)
"Lovely holiday in a beautiful location "
Beautiful Dorset Country House in the Heart of the Stunning Isle of Purbeck
Beautiful large Georgian house with a big garden. Perfect for a family or two!
Front of 29 East Street Wareham

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

10.0 out of 10, Exceptional, (68)
"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!
The Seagulls, 3 Bed Townhouse
Room

The Seagulls, 3 Bed Townhouse

8.0 out of 10, Very Good, (1)
"Overall very nice clean apartment"
The Seagulls, 3 Bed Townhouse
A charming seaside cottage 5 minutes walk from beach on Jurassic Coast
Sitting room with 4 sofas

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
Stable Conversion Near Lulworth Cove/Jurassic Coast
Terrace/patio

Stable Conversion Near Lulworth Cove/Jurassic Coast

10.0 out of 10, Exceptional, (105)
"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
5 bed, 5 bath, Slps 18, Town Ho. 60 yds Weymth beach & harbour, NEWLY RENOVATED!
Room

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

Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
Marina

Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.

10.0 out of 10, Exceptional, (1)
"Had a wonderful stay on this beautiful boat, extremely clean and tidy with all the amenities you could hope for. Excellent location and lovely marina to enjoy with great facilities. Will definitely be returning again very soon. Very highly recommended."
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
Beautiful, family friendly Cottage with sea views of Chesil Beach
Room

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
Charming Sea View Cottage in Portland Dorset
Sandsfoot Castle and it's beaches 5 minutes drive from the cottage

Charming Sea View Cottage in Portland Dorset

9.0 out of 10, Wonderful, (2)
" Tastefully decorated Cottage. Nice space clean, tidy and welcoming."
Charming Sea View Cottage in Portland 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.