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Check prices for these dates

Tonight
11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Portland holiday rentals

Deluxe Chalet, 3 Bedrooms, Resort View, Garden Area | Desk, laptop workspace, blackout curtains, iron/ironing board
The Dorset Resort

The Dorset Resort

The Dorset Resort
4.0 star property
Wareham
9.8 out of 10, Exceptional, (44)
"PRPOERTY VERY SPACIOUS, VERY CLEAN AND JUST A LOVELY PROPERTY TO UNWIND AND RELAX WITH FAMILY, LOVED THE SAUNA"
United Kingdom
tina
The Dorset Resort
Dining
18 Chamberlaine Road

18 Chamberlaine Road

18 Chamberlaine Road
2.5 star property
Weymouth
The price is ฿13,970
฿16,765 total
includes taxes & fees
14 Dec - 15 Dec
18 Chamberlaine Road
Cottage | Interior
Leo's Place

Leo's Place

Leo's Place
3.0 star property
Weymouth
Leo's Place
Cottage | Interior
The Studio - Arne

The Studio - Arne

The Studio - Arne
3.5 star property
Wareham
The price is ฿47,097
฿56,517 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Studio - Arne
Cabin | Terrace/patio
Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake

Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake

Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake
2.0 star property
Dorchester
Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake
Beach nearby
Day Cottage

Day Cottage

Day Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1)
"The cottage was absolutely excellent , clean, had everything you need,cosy, couldn’t ask for more ,also not far from the beach "
United Kingdom
Cindy
The price is ฿13,547
฿16,257 total
includes taxes & fees
14 Dec - 15 Dec
Day Cottage
Fridge, microwave, oven, stovetop
4 Bed-2 Bath-bar-pool Table-library- Xmas Venue

4 Bed-2 Bath-bar-pool Table-library- Xmas Venue

4 Bed-2 Bath-bar-pool Table-library- Xmas Venue
2.0 star property
Dorchester
The price is ฿26,053
฿36,344 total
includes taxes & fees
15 Dec - 16 Dec
4 Bed-2 Bath-bar-pool Table-library- Xmas Venue
Property grounds
Hide-a-way

Hide-a-way

Hide-a-way
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1)
The price is ฿11,924
฿14,309 total
includes taxes & fees
14 Dec - 15 Dec
Hide-a-way
Property grounds
Victoria House

Victoria House

Victoria House
3.0 star property
Weymouth
The price is ฿16,193
฿19,432 total
includes taxes & fees
14 Dec - 15 Dec
Victoria House
Cottage | Interior
Guinea Cottage

Guinea Cottage

Guinea Cottage
3.5 star property
Weymouth
10.0 out of 10, Exceptional, (1)
The price is ฿13,441
฿16,130 total
includes taxes & fees
14 Dec - 15 Dec
Guinea Cottage
House, 2 Bedrooms, Patio | Beach
Manor House Mews - Rustic Stable Conversion

Manor House Mews - Rustic Stable Conversion

Manor House Mews - Rustic Stable Conversion
3.0 star property
Dorchester
3.6 out of 10, (4)
"The property was dirty , the pull out bed had a mouse nest chewed into it , the kitchen had mouse dropping and smelt of urine , we put out a small rodent that had come up from behind the sink in the bathroom, the bed and pillows were old , uncomfortable and lumpy , we are so disappointed. And would not recommend to anyone . We had to eat out due to the kitchen being dirty and unsafe with a mouse clearly present . "
United Kingdom
Helen
Manor House Mews - Rustic Stable Conversion
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 ฿15,170
฿18,204 total
includes taxes & fees
15 Dec - 16 Dec
2 Driftwood
Room
Harbour House

Harbour House

Harbour House
2.5 star property
Weymouth
9.8 out of 10, Exceptional, (26)
"Most friendly hosts providing well fitted accommodation in a very convenient location "
United Kingdom
David
Harbour House
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 Bull Hotel

The Bull Hotel

10/10 Excellent
"Friendly staff, central location, good range of breakfast options "
Hannah 1-night trip
Posted 2 days ago
The Bull Hotel

Find out more about Portland

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

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

Yes, there are holiday rentals close to the most popular sights in Portland, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals will I find in Portland?

Choose from 18 Expedia holiday rentals in Portland for a memorable holiday.

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 holiday rentals like in Portland?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Portland. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for family gatherings.