A coastal town with colorful houses, a prominent hill in the background, and a clear blue sky.

Portland Holiday Rentals

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Our top choices for Portland holiday rentals

1. Lily's Pad

Lily's Pad
3.0 star property
Portland
The price is NZ$873
includes taxes & fees
17 Oct - 18 Oct
Lily's Pad

2. 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 NZ$668
includes taxes & fees
4 Oct - 5 Oct
Lighthouse View

3. Chandlers Nook

Chandlers Nook
2.0 star property
Portland
The price is NZ$911
includes taxes & fees
2 Oct - 3 Oct
Chandlers Nook

4. Mermaid Cottage

Mermaid Cottage
3.0 star property
Portland
10.0 out of 10, Exceptional, (1 review)
"Very nice cottage in quiet location with room opening onto garden with lots of bird song. Snug with TV is very comfortable. Parking spot just outside cottage. Well appointed kitchen. Location is good for access to portland, but going elsewhere requires travelling through Weymouth which can be slow."
United Kingdom
Terry
The price is NZ$1,167
includes taxes & fees
4 Oct - 5 Oct
Mermaid Cottage

5. Portland View

Portland View
2.0 star property
Portland
The price is NZ$1,078
includes taxes & fees
10 Oct - 11 Oct
Portland View

6. Home From Home

Home From Home
3.0 star property
Portland
The price is NZ$1,064
includes taxes & fees
14 Oct - 15 Oct
Home From Home

7. 74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is NZ$1,102
includes taxes & fees
12 Oct - 13 Oct
74 Reap Lane

8. Anchor Cottage

Anchor Cottage
3.0 star property
Portland
The price is NZ$1,136
includes taxes & fees
10 Oct - 11 Oct
Anchor Cottage

9. Old Higher Lighthouse Branscombe Lodge

Old Higher Lighthouse Branscombe Lodge
3.0 star property
Portland
10.0 out of 10, Exceptional, (1 review)
"This property was absolutely amazed and having Access to one of the first lighthouses there "
United Kingdom
Trevor
The price is NZ$1,243
includes taxes & fees
16 Oct - 17 Oct
Old Higher Lighthouse Branscombe Lodge

10. The Shambles

The Shambles
3.5 star property
Portland
The price is NZ$1,479
includes taxes & fees
2 Oct - 3 Oct
The Shambles

11. Groves House

Groves House
3.0 star property
Portland
8.0 out of 10, Very good, (1 review)
"A nice clean house in a decent location. Not far to walk for some decent pubs. Comfortable beds etc. A few small niggles. The hob was not fully functional and the kitchen tap was falling apart. Still usable though. Overall pretty decent."
United Kingdom
David
Groves House

12. Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage
3.0 star property
Portland
The price is NZ$1,243
includes taxes & fees
19 Oct - 20 Oct
Old Higher Lighthouse Stopes Cottage

13. Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is NZ$1,677
includes taxes & fees
27 Oct - 28 Oct
Pebbles Reach

14. St Johns View

St Johns View
3.5 star property
Portland
The price is NZ$1,498
includes taxes & fees
4 Oct - 5 Oct
St Johns View

15. Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is NZ$1,338
includes taxes & fees
2 Oct - 3 Oct
Bear's Apartment

16. Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is NZ$1,448
includes taxes & fees
5 Oct - 6 Oct
Manhattan Beach

17. Coastguard View

Coastguard View
3.0 star property
Portland
The price is NZ$1,365
includes taxes & fees
3 Oct - 4 Oct
Coastguard View

18. Sea Gem

Sea Gem
3.5 star property
Portland
The price is NZ$2,262
includes taxes & fees
16 Oct - 17 Oct
Sea Gem

19. The Old Portland Courthouse

The Old Portland Courthouse
3.5 star property
Portland
The price is NZ$2,884
includes taxes & fees
2 Oct - 3 Oct
The Old Portland Courthouse

20. The View

The View
2.0 star property
Portland
The price is NZ$2,119
includes taxes & fees
30 Oct - 31 Oct
The View
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Portland holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Portland. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Portland. Seeing all the best attractions is bound to make you fall in love with Portland. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Portland short-term rentals, that won’t be hard to do.

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. Some other top choices in Portland are Coastal bungalow retreat on the Jurassic Coast at Portland, Dorset. and 4 bedroom accommodation in Portland.

How many holiday rentals will I find in Portland?

Choose from 19 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.