A coastal town with colorful houses, a prominent hill in the background, and a clear blue sky.

Portland Vacation Rentals

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Check prices for these dates

In two weeks
Jul 17 - Jul 19
In two months
Aug 28 - Aug 30
In three months
Sep 25 - Sep 27
In four months
Oct 23 - Oct 25

Our top choices for Portland vacation homes

Cottage | Living room

The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is CA $1,948
CA $2,338 total
includes taxes & fees
Jul 19 - Jul 20
The Old Portland Courthouse
Iron/ironing board, WiFi, bed sheets

The Anchor Stuidio|Sleeps2|Weymouth Beach|

The Anchor Stuidio|Sleeps2|Weymouth Beach|
Dorset Weymouth
The price is CA $151
CA $293 total
includes taxes & fees
Jul 5 - Jul 6
The Anchor Stuidio|Sleeps2|Weymouth Beach|
Iron/ironing board, travel crib, WiFi, bed sheets

The Lighthouse Suite|Sleeps4|Weymouth Beach|

The Lighthouse Suite|Sleeps4|Weymouth Beach|
Dorset Weymouth
The price is CA $209
CA $370 total
includes taxes & fees
Jul 5 - Jul 6
The Lighthouse Suite|Sleeps4|Weymouth Beach|
Private kitchen

Beautiful newly refurbished annexe 2 miles from Wareham Quay

Beautiful newly refurbished annexe 2 miles from Wareham Quay
Sandford
The price is CA $205
CA $235 total
includes taxes & fees
Jul 6 - Jul 7
Beautiful newly refurbished annexe 2 miles from Wareham Quay
Beach

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

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Wool
10.0 out of 10, Exceptional, (4 reviews)
"Responsive owner and lovely property"
United Kingdom
Benjamin
The price is CA $322
CA $693 total
includes taxes & fees
Jul 9 - Jul 10
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Interior

Hardy View Farm House

Hardy View Farm House
Dorchester
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely Fabulous Stay at this Farmhouse. Wonderful hosts in Luba and Chris who were so informative and helpful.Lovely property inside and out. So relaxing and peaceful. Missing the wonderful breakfasts already. 10 out of 10 !!"
Australia
Carol S.
The price is CA $293
CA $337 total
includes taxes & fees
Jul 9 - Jul 10
Hardy View Farm House
WiFi

The Halt Maiden Newton, Dorset

The Halt Maiden Newton, Dorset
Dorchester
The price is CA $710
CA $710 total
includes taxes & fees
Jul 7 - Jul 8
The Halt Maiden Newton, Dorset
Interior

Peacehaven Retreat - 4 minutes from the beach!

Peacehaven Retreat - 4 minutes from the beach!
Weymouth
The price is CA $154
CA $241 total
includes taxes & fees
Jul 6 - Jul 7
Peacehaven Retreat - 4 minutes from the beach!
Smart TV, books

The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

The Old Police House, sleeps 10, 1850,s cottage, Family Stay!
Winterborne Whitechurch
The price is CA $737
CA $844 total
includes taxes & fees
Jul 6 - Jul 7
The Old Police House, sleeps 10, 1850,s cottage, Family Stay!
Interior

The Old Barn, Swanage

The Old Barn, Swanage
Swanage
10.0 out of 10, Exceptional, (2 reviews)
"The location allowed for a relaxing time. Plenty of space for the whole party. Ample parking .footpaths around the home to walk from.When the Steam railway is working a great view of the trains going pass.Swanage and many other attractions very close by so an ideal base. "
United Kingdom
Lucy N.
The price is CA $2,297
CA $2,297 total
includes taxes & fees
Jul 18 - Jul 19
The Old Barn, Swanage
Exterior

8 Driftwood

8 Driftwood
3.5 star property
Bridport
10.0 out of 10, Exceptional, (1 review)
"Great place and so close to everything, balcony needs a bit of a clean and the view was a bit disappointing but overall had a great time "
United Kingdom
kevin
The price is CA $711
CA $853 total
includes taxes & fees
Jul 18 - Jul 19
8 Driftwood
Beach

The Studio - Arne, Stoborough

The Studio - Arne, Stoborough
Wareham
The price is CA $8,159
CA $8,159 total
includes taxes & fees
Jul 17 - Jul 18
The Studio - Arne, Stoborough
Dining

4/5 Bed-2 Bath-bar-pool Table-library-parking For7

4/5 Bed-2 Bath-bar-pool Table-library-parking For7
3.0 star property
Dorchester
The price is CA $1,147
CA $1,604 total
includes taxes & fees
Jul 20 - Jul 21
4/5 Bed-2 Bath-bar-pool Table-library-parking For7
Cottage | Interior

Seacliff

Seacliff
2.0 star property
Bridport
10.0 out of 10, Exceptional, (1 review)
"This is our second time staying at Seacliffe and it was perfect for us as a family of 5 and a small dog. The house has everything you need, lots of space and a lovely patio and garden."
United Kingdom
Vicki
The price is CA $1,458
CA $1,749 total
includes taxes & fees
Jul 15 - Jul 16
Seacliff
Exterior

The Courthouse

The Courthouse
3.5 star property
Weymouth
The price is CA $1,326
CA $1,591 total
includes taxes & fees
Jul 17 - Jul 18
The Courthouse
Cottage | Private kitchen

Weybury Cottage

Weybury Cottage
3.5 star property
Weymouth
The price is CA $1,439
CA $1,726 total
includes taxes & fees
Jul 9 - Jul 10
Weybury Cottage
Cottage | Private kitchen

15 Hardwick Street

15 Hardwick Street
3.5 star property
Weymouth
The price is CA $1,382
CA $1,659 total
includes taxes & fees
Jul 12 - Jul 13
15 Hardwick Street
Cottage | Interior

Low Tide

Low Tide
3.0 star property
Weymouth
The price is CA $2,446
CA $2,935 total
includes taxes & fees
Jul 9 - Jul 10
Low Tide
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 Portland Hotel Reviews

Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

10/10 Excellent
"Staff on arrival was lovely; sorted us out for swimming and told us how to get down to the beach, gave Extra tea bags, friendly. Room was lovely and clean fan provided will book again"
Emily 1-night trip
Posted 4 hours ago
Best Western Weymouth Hotel Rembrandt

Find out more about Portland

Portland Vacation Homes information

Number of reviews
11
Accommodation
221 Vacation Homes
Lowest Price
CA $235
Highest Price
CA $8,159