Portland Holiday Rentals

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Our top choices for Portland holiday rentals

Mermaid Cottage

Mermaid Cottage
3.0 star property
Portland
The price is AU$934
includes taxes & fees
7 June - 8 June
Mermaid Cottage

Home From Home

Home From Home
3.0 star property
Portland
The price is AU$894
includes taxes & fees
5 June - 6 June
Home From Home

74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is AU$883
includes taxes & fees
6 June - 7 June
74 Reap Lane

Coastguard View

Coastguard View
3.0 star property
Portland
The price is AU$1,093
includes taxes & fees
5 June - 6 June
Coastguard View

Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage
3.0 star property
Portland
The price is AU$1,393
includes taxes & fees
15 June - 16 June
Old Higher Lighthouse Stopes Cottage

Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is AU$1,160
includes taxes & fees
13 June - 14 June
Manhattan Beach

The Shambles

The Shambles
3.5 star property
Portland
The price is AU$1,184
includes taxes & fees
10 June - 11 June
The Shambles

Anchor Cottage

Anchor Cottage
3.0 star property
Portland
The price is AU$909
includes taxes & fees
23 June - 24 June
Anchor Cottage

Lighthouse View

Lighthouse View
3.5 star property
Portland
6.0 out of 10, (1 review)
"Bed was not comfy as we had backache after second night , we turned mattress round was ok that night but the after that . The step into the shower was too high and we had to buy a step to get in it and also the floor surface was very slippy . Was ck an and tidy and overall not a bad place to stay and would recommend and return at some point "
United Kingdom
Anonymous traveller
The price is AU$535
includes taxes & fees
6 June - 7 June
Lighthouse View

Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is AU$1,072
includes taxes & fees
19 June - 20 June
Bear's Apartment

The View

The View
2.5 star property
Portland
The price is AU$1,503
includes taxes & fees
5 June - 6 June
The View

Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is AU$1,343
includes taxes & fees
6 June - 7 June
Pebbles Reach

St Johns View

St Johns View
3.5 star property
Portland
The price is AU$1,635
includes taxes & fees
6 June - 7 June
St Johns View

Sea Gem

Sea Gem
3.5 star property
Portland
The price is AU$1,811
includes taxes & fees
5 June - 6 June
Sea Gem

Littlesea Holiday Park - Holiday Accommodation 19270

Littlesea Holiday Park - Holiday Accommodation 19270
2.5 star property
Weymouth
The price is AU$783
includes taxes & fees
13 June - 14 June
Littlesea Holiday Park - Holiday Accommodation 19270

Duck Cottage, Sutton Poyntz

Duck Cottage, Sutton Poyntz
Weymouth
The price is AU$1,042
includes taxes & fees
6 June - 7 June
Duck Cottage, Sutton Poyntz

The Halt Maiden Newton, Dorset

The Halt Maiden Newton, Dorset
Dorchester
The price is AU$614
includes taxes & fees
4 June - 5 June
The Halt Maiden Newton, Dorset

Fisherman's Rest, Wyke Regis

Fisherman's Rest, Wyke Regis
Weymouth
The price is AU$1,396
includes taxes & fees
4 June - 5 June
Fisherman's Rest, Wyke Regis

Pebbles Foxglove Way, West Bay

Pebbles Foxglove Way, West Bay
Bridport
The price is AU$1,457
includes taxes & fees
4 June - 5 June
Pebbles Foxglove Way, West Bay

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 AU$1,497
includes taxes & fees
4 June - 5 June
The Old Barn, Swanage
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

Find out more about Portland

Everything you need to know about Portland holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Portland holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Portland holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Portland holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Portland. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Portland holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland holiday rentals we have selected for you start as low as AU$894 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Portland rentals

At Expedia, we put the best Portland holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Portland rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Portland holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Portland. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Portland?

Yes, there are holiday rentals in Portland close to Osprey Leisure Centre, 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.

What are some of the best holiday rentals that Portland has to offer?

Beautiful, family friendly Cottage with sea views of Chesil Beach : This highly rated holiday home rental in Portland is located in a rural location, and has a fireplace, a private garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Our travellers also rate Bright & beautiful 4 bedroom house with sea views as a favourite home for rent in Portland.

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.