Portland Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In one month
In two months
In three months

Holiday Rentals in Portland

Our top choices for Portland holiday rentals

Beautiful, family friendly Cottage with sea views of Chesil Beach

9.8 out of 10, Exceptional, (21)
"Great little cottage, within walking distance of the beach. Great host "
Beautiful, family friendly Cottage with sea views of Chesil Beach

Home From Home

3.0 star property
The price is AU$942
includes taxes & fees
7 Sept - 8 Sept
Home From Home

Panoramic View

3.5 star property
Panoramic View

65 Ocean View

3.0 star property
The price is AU$952
includes taxes & fees
8 Sept - 9 Sept
65 Ocean View

The View

2.5 star property
The price is AU$1,585
includes taxes & fees
14 Sept - 15 Sept
The View

The Dorset Resort

4.0 star property
9.8 out of 10, Exceptional, (40)
"PRPOERTY VERY SPACIOUS, VERY CLEAN AND JUST A LOVELY PROPERTY TO UNWIND AND RELAX WITH FAMILY, LOVED THE SAUNA"
The Dorset Resort

Luxury Pine Wood Lodge, situated in beautiful Dorset Countryside,attractions nr

9.2 out of 10, Wonderful, (88)
"Great location for a peaceful family stay. beautiful surroundings."
Luxury Pine Wood Lodge, situated in beautiful Dorset Countryside,attractions nr

4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly

2.0 star property
The price is AU$658
includes taxes & fees
1 Sept - 2 Sept
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly

Apartment with stunning Sea View

9.4 out of 10, Exceptional, (56)
"We stayed over a long weekend so I could participate in the Ultra Challenge event and see a little bit of the local area. The weather was good and we had an enjoyable stay. The location is West Bay was ideal for our needs as well as being quiet so restful as well."
Apartment with stunning Sea View

Self Contained Garden Studio With Private Decked Terrace, close to town and sea

9.6 out of 10, Exceptional, (139)
"Lovely studio with everything you needed very friendly and helpful hosts "
Self Contained Garden Studio With Private Decked Terrace, close to town and sea

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

10.0 out of 10, Exceptional, (48)
"An excellent property in a great location."
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

Luxury Apartment close to shops, coast and stunning beaches. Far reaching views

10.0 out of 10, Exceptional, (72)
"nice location, clean apartment and very well equipped for a short break!"
Luxury Apartment close to shops, coast and stunning beaches. Far reaching views

18 Chamberlaine Road

2.5 star property
The price is AU$818
includes taxes & fees
10 Sept - 11 Sept
18 Chamberlaine Road

Luxury mobile home with spectacular sea views.

9.8 out of 10, Exceptional, (118)
"Very clean, great communication, amazing views."
Luxury mobile home with spectacular sea views.

Apartment near the beach with private parking and pet friendly

9.2 out of 10, Wonderful, (28)
"Couldn't as for more, clean, lovely little property about 10 mins from the beach and town center."
Apartment near the beach with private parking and pet friendly

Dorchester Nook

9.6 out of 10, Exceptional, (4)
"Fiona is a very friendly host, and we had a nice room, well located in the centre of the town! "
The price is AU$186
includes taxes & fees
2 Sept - 3 Sept
Dorchester Nook

Bay View Luxury Stays - Mount Pleasant, 6 bed with indoor pool

10.0 out of 10, Exceptional, (9)
"The property is done up to a really high standard and was ideal for our group. Great Facilities, kids had a blast Location is fabulous"
Bay View Luxury Stays - Mount Pleasant, 6 bed with indoor pool

Charming Country Retreat on Old Sherbourne Road

8.0 out of 10, Very good, (1)
"A small cottage with a lovely terrace in the countryside above the road at the edge of a field. Very sustainably run and beautifully furnished. A short walk to town and the beach.Tracy is a very pleasant host."
Charming Country Retreat on Old Sherbourne Road

The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

9.6 out of 10, Exceptional, (44)
"A lovely relaxed stay, nice peaceful area, plenty of places to walk, highly recommend gor a bit of r&r."
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

Hidden Retreat - 4 mins to beach & 3 mins to train station. Pet friendly!

8.0 out of 10, Very good, (7)
"Lovely host, well presented and loved the fact it had a bbq. Travel cot provided which helped good communication with host. "
Hidden Retreat - 4 mins to beach & 3 mins to train station. Pet friendly!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Portland Hotel Reviews

Find out more about Portland

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$186 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 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.

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.

How many holiday rentals will I find in Portland?

Choose from 17 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.