Holiday Rentals in Portland

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Holiday Rentals in Portland

Beautiful, family friendly Cottage with sea views of Chesil Beach

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

The View

2.5 star property
Portland
The price is €872
includes taxes & fees
13 Nov - 14 Nov
The View

Home From Home

3.0 star property
Portland
The price is €519
includes taxes & fees
13 Nov - 14 Nov
Home From Home

The Dorset Resort

4.0 star property
Wareham
9.8 out of 10, Exceptional, (44)
"I have stayed here a few times, never been disappointed and will always come back for another visit."
United Kingdom
ASHAN
The Dorset Resort

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

Maiden Newton
9.6 out of 10, Exceptional, (45)
"Lovely airy cottage - exactly as it looks on the website.Perfect for a quiet retreat."
United Kingdom
Roger A.
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

Luxury mobile home with spectacular sea views.

Weymouth
9.8 out of 10, Exceptional, (123)
"Good well maintained caravan, very clean and a very nice outlook from nice balcony. "
United Kingdom
Craig W.
Luxury mobile home with spectacular sea views.

Private detached cottage to rent on Chesil Beach

Abbotsbury
10.0 out of 10, Exceptional, (68)
"Beautiful property, well equipped with all amenities, very cosy and comfortable. The highlight was the location and if you looking to get away from it all, this is the perfect place."
United States
David Walker & B.
Private detached cottage to rent on Chesil Beach

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

Wyke Regis
10.0 out of 10, Exceptional, (109)
"Lovely property, quiet location, very well equipped exactly what I wanted."
United Kingdom
Jennie N.
Quiet location, short walk to beach, with views of Portland and Jurassic coast

18 Chamberlaine Road

2.5 star property
Weymouth
The price is €451
includes taxes & fees
13 Nov - 14 Nov
18 Chamberlaine Road

The Studio - Arne

3.5 star property
Wareham
The price is €1,562
includes taxes & fees
13 Nov - 14 Nov
The Studio - Arne

Charming Country Retreat on Old Sherbourne Road

Dorchester
9.0 out of 10, Wonderful, (2)
"A lovely little cabin hidden away for a break away, and a place to reset, So close to the beach and Weymouth town too was also a plus. thank you to Tracy the lovely host who made us feel so welcome."
United Kingdom
Suzie E.
Charming Country Retreat on Old Sherbourne Road

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

2.0 star property
Dorchester
The price is €346
includes taxes & fees
1 Dec - 2 Dec
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly

Apartment near the beach with private parking and pet friendly

Weymouth
9.0 out of 10, Wonderful, (30)
"Lovely flat, spotlessly clean. Good central location. Good facilities, only 2minor things, the shower head needed descaling as the holes were mainly blocked, and the 2hand basins did not hold water it kept draining out. Otherwise a brilliant place to stay for a week in Weymouth. "
United Kingdom
elaine g.
Apartment near the beach with private parking and pet friendly

Leo's Place

3.0 star property
Weymouth
The price is €725
includes taxes & fees
13 Nov - 14 Nov
Leo's Place

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

Langton Matravers
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. "
United Kingdom
Alison K.
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight

Ocean Swell

3.5 star property
Weymouth
The price is €713
includes taxes & fees
13 Nov - 14 Nov
Ocean Swell

Upwey - Wessex Quarters

Weymouth
8.0 out of 10, Very good, (1)
"Excellent location. Well priced convenient parking near property "
United Kingdom
rachel g.
Upwey - Wessex Quarters

Historical, Characterful, Converted Old School House

Lower Bockhampton
9.0 out of 10, Wonderful, (2)
"Very nice clean well furnished"
United States
Stephen Z.
Historical, Characterful, Converted Old School House

Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Weymouth
8.8 out of 10, Excellent, (45)
"This property is in need of some tlc. If you are using the loft room it has wooden steep stairs and no handrail at all which made it extremely difficult to access. There is NO on site parking as advertised in fact there is NO parking near the property at all. Had to park some streets away which were not permit parking like outside the property, this caused friction with the owners of the house that we parked in front of which we ended up getting verbally abused for. Kettle was dirty and needed...
United Kingdom
Keith
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake

2.0 star property
Dorchester
Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake
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, apart-hotels, 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 €346 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.