Portland Holiday Rentals

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Holiday Rentals in Portland

Our top choices for Portland holiday rentals

One bed apartment next to Chesil Beach Dorset

9.2 out of 10, Wonderful, (7)
"Nice clean property ideal for a couple to have a weekend away . Close to shops, takeaways and the beach . "
One bed apartment next to Chesil Beach Dorset

Home From Home

3.0 star property
The price is NZ$1,038
includes taxes & fees
29 Sept - 30 Sept
Home From Home

Beautiful, family friendly Cottage with sea views of Chesil Beach

9.4 out of 10, Exceptional, (23)
"Great little cottage, within walking distance of the beach. Great host "
Beautiful, family friendly Cottage with sea views of Chesil Beach

The View

2.5 star property
The View

The Dorset Resort

4.0 star property
9.8 out of 10, Exceptional, (42)
"PRPOERTY VERY SPACIOUS, VERY CLEAN AND JUST A LOVELY PROPERTY TO UNWIND AND RELAX WITH FAMILY, LOVED THE SAUNA"
The Dorset Resort

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

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

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.

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

10.0 out of 10, Exceptional, (50)
"Outstanding house in ideal location. I could have sat in the garden all week!"
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

Apartment with stunning Sea View

9.4 out of 10, Exceptional, (58)
"Fabulous location, just yards from the beach. Lots of places to eat and drink within easy walking distance.The flat was beautifully clean, spacious and comfortable and the kitchen well equipped.So many beautiful walks on the doorstep!We had a lovely stay."
Apartment with stunning Sea View

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

10.0 out of 10, Exceptional, (2)
"A wonderful experience - THANK YOU!"
The price is NZ$622
includes taxes & fees
21 Sept - 22 Sept
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Apartment near the beach with private parking and pet friendly

9.2 out of 10, Wonderful, (29)
"Quite close to local park to walk the dog. Allocated car parking space which was useful. Clean and tidy apartment. "
Apartment near the beach with private parking and pet friendly

Dorchester Nook

8.8 out of 10, Excellent, (5)
"The en-suite room in Fiona's home was perfect for our short stay. The bed and pillows were very comfortable and we had a lovely peaceful sleep. The shower was really powerful, nice big bath towels and shampoo, conditioner and body wash were provided. The location was great for us to visit Weymouth and Durdle Door. Thanks for having us!"
The price is NZ$196
includes taxes & fees
23 Sept - 24 Sept
Dorchester Nook

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

2.0 star property
The price is NZ$726
includes taxes & fees
17 Sept - 18 Sept
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly

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

10.0 out of 10, Exceptional, (10)
"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

18 Chamberlaine Road

2.5 star property
The price is NZ$902
includes taxes & fees
19 Sept - 20 Sept
18 Chamberlaine Road

Private detached cottage to rent on Chesil Beach

10.0 out of 10, Exceptional, (68)
"It was once again a perfect stay."
Private detached cottage to rent on Chesil Beach

Quiet location, short walk to beach, with views of Portland and Jurassic coast

10.0 out of 10, Exceptional, (103)
"Lovely house in a great area for the beaches and walks. "
Quiet location, short walk to beach, with views of Portland and Jurassic coast

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

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.
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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 favorite 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 depends 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 NZ$196 per night. Entering your travel dates in the search wizard you might find 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.