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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Holiday Rentals in Portland

Our top choices for Portland holiday rentals

Beautiful, family friendly Cottage with sea views of Chesil Beach
Beach nearby

Beautiful, family friendly Cottage with sea views of Chesil Beach

9.6 out of 10, Exceptional, (20)
"Great little cottage, within walking distance of the beach. Great host "
Beautiful, family friendly Cottage with sea views of Chesil Beach
Panoramic View
Interior

Panoramic View

3.5 star property
Panoramic View
65 Ocean View
Dining

65 Ocean View

3.0 star property
The price is HK$4,038
HK$4,846 total
includes taxes & fees
4 Sept - 5 Sept
65 Ocean View
The Dorset Resort
3 bedrooms, desk, laptop workspace, blackout curtains

The Dorset Resort

4.0 star property
10.0 out of 10, Exceptional, (37)
"Amazing properties set in a beautiful tranquil setting. Wildlife everywhere and great for children to be outdoors, lovely walks and grounds. "
The Dorset Resort
Apartment with stunning Sea View
Exterior

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
Exterior detail

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
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly
Fridge, microwave, oven, stovetop

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

2.0 star property
The price is HK$1,933
HK$3,330 total
includes taxes & fees
8 Sept - 9 Sept
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly
Dorchester Nook
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 HK$710
HK$931 total
includes taxes & fees
31 Aug - 1 Sept
Dorchester Nook
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Terrace/patio

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
Apartment near the beach with private parking and pet friendly
Fridge, microwave, oven, stovetop

Apartment near the beach with private parking and pet friendly

9.4 out of 10, Exceptional, (26)
"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
Luxury Apartment close to shops, coast and stunning beaches. Far reaching views
Marina

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

10.0 out of 10, Exceptional, (71)
"nice location, clean apartment and very well equipped for a short break!"
Luxury Apartment close to shops, coast and stunning beaches. Far reaching views
Luxury mobile home with spectacular sea views.
Beach nearby

Luxury mobile home with spectacular sea views.

9.8 out of 10, Exceptional, (116)
"Very clean, great communication, amazing views."
Luxury mobile home with spectacular sea views.
Bay View Luxury Stays - Mount Pleasant, 6 bed with indoor pool
Dining

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
Terrace/patio

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
A beautiful comfortable cottage in the centre of Bridport.
Beach

A beautiful comfortable cottage in the centre of Bridport.

A beautiful comfortable cottage in the centre of Bridport.
Hidden Retreat - 4 mins to beach & 3 mins to train station. Pet friendly!
Outdoor dining

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

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

10.0 out of 10, Exceptional, (100)
"Lovely house in a great area for the beaches and walks. "
Quiet location, short walk to beach, with views of Portland and Jurassic coast
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Beach

Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight

9.4 out of 10, Exceptional, (68)
"Lovely old cottage in a peaceful setting with wonderful countryside views. Great walks directly from the cottage and easy access to local places of interest. "
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Private detached cottage to rent on Chesil Beach
Dining

Private detached cottage to rent on Chesil Beach

10.0 out of 10, Exceptional, (67)
"Stunning location. The house was perfect for a proper break away from it all. Walks, beach fishing and plenty of places to visit nearby."
Private detached cottage to rent on Chesil Beach
Ocean Retreat by Wessex Quarters
Smart TV

Ocean Retreat by Wessex Quarters

6.0 out of 10, (1)
"The property is spacious for two people; however, it was not properly cleaned when we arrived. Under the sink was a leak or something, and there were cobwebs in the kitchen area. The trays in the oven are full of oil, so when you're trying to cook something in the oven, the kitchen is full of that smell, and the cooker hood would not even get the smell out. The bed was uncomfortable, and the sofa in the living area was not good either. The entrance is from the road just in front of the bus stop,...
Ocean Retreat by Wessex Quarters
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
Sign in
Sign up, it's free

Top Portland Hotel Reviews

Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

10/10 Excellent
"We chose this hotel because it has parking. The location was fine and only a few minutes walk from the beach front. Cleanliness, staff and breakfast were all good."
David 1-night trip
Posted 18 hours ago
Best Western Weymouth Hotel Rembrandt

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.