Photo by David P Howard

Portland Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Portland vacation rentals

Cottage | Interior
Old Higher Lighthouse Branscombe Lodge

Old Higher Lighthouse Branscombe Lodge

Old Higher Lighthouse Branscombe Lodge
3.0 star property
Portland
10.0 out of 10, Exceptional, (1)
"This property was absolutely amazed and having Access to one of the first lighthouses there "
United Kingdom
Trevor
The price is ₩864,664
₩1,037,597 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Old Higher Lighthouse Branscombe Lodge
Cottage | Interior
The Shambles

The Shambles

The Shambles
3.5 star property
Portland
The price is ₩1,002,678
₩1,203,214 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Shambles
Beach nearby
Home From Home

Home From Home

Home From Home
3.0 star property
Portland
The price is ₩758,244
₩909,893 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Home From Home
Beach nearby
74 Reap Lane

74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is ₩734,964
₩881,957 total
includes taxes & fees
Jan 2 - Jan 3, 2026
74 Reap Lane
Cottage | Interior
Pebbles Reach

Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is ₩1,168,959
₩1,402,751 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Pebbles Reach
Outdoor dining
Mermaid Cottage

Mermaid Cottage

Mermaid Cottage
3.0 star property
Portland
The price is ₩798,151
₩957,781 total
includes taxes & fees
Dec 30 - Dec 31
Mermaid Cottage
Beach nearby
Manhattan Beach

Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is ₩991,038
₩1,189,246 total
includes taxes & fees
Dec 30 - Dec 31
Manhattan Beach
Beach nearby
Bear's Apartment

Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is ₩891,269
₩1,069,523 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Bear's Apartment
Interior
Groves House

Groves House

Groves House
3.0 star property
Portland
The price is ₩771,546
₩925,855 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Groves House
Cottage | Interior
Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage
3.0 star property
Portland
The price is ₩864,664
₩1,037,597 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Old Higher Lighthouse Stopes Cottage
Cottage | Interior
Kimberlin

Kimberlin

Kimberlin
3.5 star property
Portland
The price is ₩974,410
₩1,169,292 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Kimberlin
Cottage | Interior
St Johns View

St Johns View

St Johns View
3.5 star property
Portland
St Johns View
Cottage | Interior
Sea Gem

Sea Gem

Sea Gem
3.5 star property
Portland
The price is ₩1,533,116
₩1,839,739 total
includes taxes & fees
Dec 30 - Dec 31
Sea Gem
Cottage | Interior
Jurassic Coast House

Jurassic Coast House

Jurassic Coast House
3.5 star property
Portland
8.0 out of 10, Very Good, (1)
"Nice size property. Missing the more luxury/comfort items. Garden furniture ok not as images. Has a comfy dining table. Balcony furniture present but not suitable for the area. High stools and table not appropriate needs more relaxing items to make area useful otherwise it was good for drying clothes. Area is central and easy for amenities, cafes, beach, shops etc all easy to walk to. Noisy as near heliport and some days this is busy from early morning till after 10 at night. Not overly...
United Kingdom
Michelle
The price is ₩1,681,106
₩2,017,327 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Jurassic Coast House
Cottage | Beach | Beach nearby
The View

The View

The View
2.5 star property
Portland
The price is ₩1,308,636
₩1,570,363 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The View
Cottage | Balcony
The Old Portland Courthouse

The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is ₩1,955,471
₩2,346,565 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Old Portland Courthouse
Cottage | Marina
2 Driftwood

2 Driftwood

2 Driftwood
3.5 star property
Bridport
10.0 out of 10, Exceptional, (2)
"2 Driftwood was a perfect place to stay at the perfect location of West Bay. The flat is very new, immaculate and well equipped with all you need for a holiday stay. Only one issue we had was finding the meter cupboard where the key safe was located. This is outside of the rear entrance of the building at ground level. One of the residents advised us of the key safe location and said many other guests had struggled with this. Everything else was perfect and Iwould love to live there."
United Kingdom
Debbie
The price is ₩715,011
₩858,013 total
includes taxes & fees
Jan 3 - Jan 4, 2026
2 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Portland Hotel Reviews

Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

10/10 Excellent
"The room was nicely appointed and clean, staff were helpful and friendly. Would stay there again."
Susan 2-night trip
Posted 6 days ago
Best Western Weymouth Hotel Rembrandt

Find out more about Portland

Search for Vacation rentals in Portland on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Portland using one of the methods below:

  • View our selection of featured Vacation rentals in Portland
  • Use the map to find apartments and other Vacation homes in the Portland neighbourhood you prefer
  • Enter your travel dates to view the best deals on Vacation rentals in Portland while they last

Look no further and take a look at our great range of rental properties in Portland!

Frequently asked questions

Can I find a vacation rental in Portland?

Yes, you can find vacation rentals close to popular sights in Portland, or you can select a more remote option if you'd like a relaxing place to stay. Tourists appreciate the top-notch restaurants and bars in Portland. Make sure you have time to check out the university setting while you're in the area.

How many vacation rentals will I find in Portland?

Choose from 17 Expedia vacation rentals in Portland for a memorable vacation.

What can I see and do in Portland?

Cultural attractions include Portland Museum and Tout Quarry Sculpture Park, whereas Portland Bill and Weymouth Bay are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Portland Harbour and Portland Bill Lighthouse.

What are vacation rentals like in Portland?

Vacation rentals are private properties you can stay in for a couple days or more in Portland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.