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
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Portland vacation homes

A spacious loft with high ceilings, exposed wooden beams, and large windows.

1. The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is CA $1,934
CA $2,321 total
includes taxes & fees
Oct 13 - Oct 14
The Old Portland Courthouse
A marina with boats docked, a statue in the foreground, and buildings in the background.

2. The Lighthouse Suite|Sleeps4|Weymouth Beach|

The Lighthouse Suite|Sleeps4|Weymouth Beach|
Weymouth Town Center
6.0 out of 10, (1 review)
"Property very difficult to find as out of date pictures & false impression of outside. Property inside was fairly clean. But access stairs & Outlook really let it down as not clean. Apartmentment was well equipped & comfortable. Sadly shower was not working nor was the fan in the bathroom. It is however in a very noisy area late at night & early in the morning, so personally would not stay here with children. However it is very close to all amenities."
United Kingdom
Lynn
The price is CA $132
CA $292 total
includes taxes & fees
Oct 11 - Oct 12
The Lighthouse Suite|Sleeps4|Weymouth Beach|
A window view of a beach with a white fence, a palm tree, and a lighthouse in the distance.

3. Low Tide

Low Tide
3.0 star property
Weymouth Town Center
The price is CA $2,431
CA $2,917 total
includes taxes & fees
Oct 13 - Oct 14
Low Tide
A beach with a natural rock arch formation.

4. 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, (5 reviews)
"The house was outstanding, probably the best we’ve ever experienced. It is exceptionally clean, comfortable for our family of 5, and convenient to the sites in the area. We would stay there again if we return."
United States
Kristina
The price is CA $169
CA $514 total
includes taxes & fees
Oct 11 - Oct 12
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
A modern kitchen with grey cabinets, a stainless steel sink, and a gas stove.

5. Beautiful newly refurbished annexe 2 miles from Wareham Quay

Beautiful newly refurbished annexe 2 miles from Wareham Quay
Sandford
The price is CA $203
CA $233 total
includes taxes & fees
Nov 2 - Nov 3
Beautiful newly refurbished annexe 2 miles from Wareham Quay
A bathroom with a window, a sink, and two potted plants.

6. Hardy View Farm House

Hardy View Farm House
Dorchester
10.0 out of 10, Exceptional, (3 reviews)
The price is CA $301
CA $344 total
includes taxes & fees
Oct 26 - Oct 27
Hardy View Farm House
A cozy room with exposed brick walls, wooden beams, and a mix of leather and fabric seating.

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

The Old Police House, sleeps 10, 1850,s cottage, Family Stay!
Winterborne Whitechurch
10.0 out of 10, Exceptional, (2 reviews)
"Excellent cottage! Super quirky and perfect for a large group. My husband’s family all met at the Langham vineyard (jut 8 minute’s drive up the road from the accommodation) to celebrate his 50th ; adults, kids, dog…we had a wonderful time and carried on the celebrations with an evening of chat in the comfortable lounge and some food in the spacious dining area before heading to bed (all 10 of us). Martin was a wonderful host, very quick responses and super accommodating. The whole area is...
United States
Stacia B.
The price is CA $629
CA $715 total
includes taxes & fees
Nov 2 - Nov 3
The Old Police House, sleeps 10, 1850,s cottage, Family Stay!
A modern kitchen with stainless steel appliances, wooden countertops, and a herringbone floor pattern.

8. 15 Hardwick Street

15 Hardwick Street
3.5 star property
Weymouth Town Center
The price is CA $1,372
CA $1,647 total
includes taxes & fees
Oct 14 - Oct 15
15 Hardwick Street
A dining area with a table set for four, a bottle of wine, and a bowl of fruit.

9. Weybury Cottage

Weybury Cottage
3.5 star property
Rodwell
The price is CA $1,075
CA $1,290 total
includes taxes & fees
Oct 19 - Oct 20
Weybury Cottage
A stone house with a sloped roof, a wooden door, and a gravel driveway.

10. The Courthouse

The Courthouse
3.5 star property
Weymouth
The price is CA $1,316
CA $1,580 total
includes taxes & fees
Oct 13 - Oct 14
The Courthouse
A view from a room with a glass door leading to a balcony with a wooden railing.

11. Village View

Village View
3.0 star property
Bridport
The price is CA $797
CA $956 total
includes taxes & fees
Oct 15 - Oct 16
Village View
A beach with a large cliff and ocean waves.

12. 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 $1,449
CA $1,739 total
includes taxes & fees
Oct 13 - Oct 14
Seacliff
A modern two-story house with a sloped metal roof and a white facade.

13. 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 $705
CA $846 total
includes taxes & fees
Oct 13 - Oct 14
8 Driftwood
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

The Jubilee Hotel East- with Spa Facilities

The Jubilee Hotel East- with Spa Facilities

8/10 Good
"The staff were all helpful and friendly. Our room was clean and we had a sea view room. Only thing was because the building is old that the sash window didn't close right. Breakfast was very good."
Jane 2-night trip
Posted 22 hours ago
The Jubilee Hotel East- with Spa Facilities

Find out more about Portland

Portland Vacation Homes information

Number of reviews
13
Accommodation
238 Vacation Homes
Lowest Price
CA $233
Highest Price
CA $2,917