Portland Holiday Rentals

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Holiday Rentals in Portland

Property grounds
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
10.0 out of 10, Exceptional, (1)
"Had a wonderful stay on this beautiful boat, extremely clean and tidy with all the amenities you could hope for. Excellent location and lovely marina to enjoy with great facilities. Will definitely be returning again very soon. Very highly recommended."
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
Exterior
Beautiful, family friendly Cottage with sea views of Chesil Beach
9.6 out of 10, Exceptional, (14)
"Had a lovely time good central location. Nice place to stay better than a B&B"
Beautiful, family friendly Cottage with sea views of Chesil Beach
Living area
Two Bedroomed Bungalow at Cove Holiday Park
9.8 out of 10, Exceptional, (73)
"We were meet by lesley at the bungalow after letting her know rough time we would arrive. She had put the heater on to warm us up as it was wet and cold out. She showed us around it has everything you would need for a get away. Fresh clean towels nice fresh bedding on all the beds. Milk and water in the fridge,.She even managed to save us a trip to Weymouth to get gluten-free fish and chips by recommending a local place that delivered. And they were great fresh thick chips. Nice quite location...
Two Bedroomed Bungalow at Cove Holiday Park
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Property grounds
Charming Sea View Cottage in Portland Dorset
10.0 out of 10, Exceptional, (1)
"123 Fortuneswell is great for tbose of us who want to explore an area and feel part of a community. FORTUNESWELL is ideal for its amazing outstanding natural beauty the views are really amazing. The cottage is set in the village near to amenities. You only have to walk down the hill to the promenade which has 2 superb eating venues .the cottage is by 2 brilliant bus services to portland and Weymouth really easy .We had no problem parking just down the road. Fortuneswell is a beautiful village...
Charming Sea View Cottage in Portland Dorset
Beach nearby
Luxury mobile home with spectacular sea views.
9.8 out of 10, Exceptional, (98)
"Beautiful view. Very clean and comfortable. Everything we needed was provided. Great stay Thank you Niell"
Luxury mobile home with spectacular sea views.
View from property
No.26 Marina View apartment, parking permit, harbour and Marina views
10.0 out of 10, Exceptional, (5)
"Fabulous location and great accommodation. We were first time visitors to the area and absolutely loved it. The apartment is spacious and well cared for with everything you need for a short stay. Would definitely recommend and we hope to return."
No.26 Marina View apartment, parking permit, harbour and Marina views
Beach nearby, sun-loungers
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
10.0 out of 10, Exceptional, (75)
"The cottage is so comfortable, well-located, and well-equipped. I could not have asked for a better experience. Thank you!"
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Outdoor dining
The Heart of a Dorset Village
The Heart of a Dorset Village
Fridge, microwave, oven, stovetop
Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset
10.0 out of 10, Exceptional, (71)
"This was a lovely little cottage. Very comfortable and the owners were great. It was in the middle of no where and was so peaceful, made perfect with the beautiful horses in the field at the bottom of the garden who always came over to see us all and put dog. The kids could wander and often went trekking in the fields searching for the different wildlife. Will certainly be back. "
Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset
Fridge, microwave, oven, stovetop
Luxury Detached House and Grounds, also benefits from full disabled facilities.
9.4 out of 10, Exceptional, (65)
"Perfect property for our trip with teens, grandparents, extended family and our 2 well behaved dogs. Wonderful space, facilities and views. Host very attentive and excellent communication. We needed somewhere we could access with a wheelchair abd this property was well designed for easy access, a lift and multiple wet rooms. Enjoyed large family dining and quality time in the open planned living space. Highly recommend !"
Luxury Detached House and Grounds, also benefits from full disabled facilities.
Property grounds
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
9.6 out of 10, Exceptional, (109)
"Julia and Paul are great hosts, the welcome pack was useful, the location to Bridport is excellent. This was the third time we have been here and will go again in the future. Thanks to our hosts."
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
Bar (on property)
Weymouth, Dorset - Pebble Bank with stunning views of Chesil Beach
9.4 out of 10, Exceptional, (20)
"Very nice"
Weymouth, Dorset - Pebble Bank with stunning views of Chesil Beach
Signature Chalet, 3 Bedrooms, Accessible, Sauna
The Dorset Resort
4.0 star property
10.0 out of 10, Exceptional, (22)
"Everything was great with our visit! The lodge was easy to locate, immaculate, and the staff at the check in desk were fantastic. Would definitely stay here again! The private sauna in the lodge was brilliant too! Couldn't fault the visit at all"
The Dorset Resort
Beach
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
9.6 out of 10, Exceptional, (56)
"Great view, good location for base for coastal footpath walking. Property well equipped."
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Exterior
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
10.0 out of 10, Exceptional, (37)
"Had a really great stay here. House was clean, tidy and modern. Views are fantastic. Will go back"
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Fridge, microwave, oven, stovetop
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
9.4 out of 10, Exceptional, (16)
"Lots of room for the kids house was delightfully cool despite the heat-wave Barbecues excellent!!Well equipped for family getaways.Great position for coast & walks .Enjoyed by all!"
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
Interior
Beachside, stunning apartment with sea and harbour views
9.8 out of 10, Exceptional, (52)
"Lots of places to eat. Great place to relax and watch the world go by."
Beachside, stunning apartment with sea and harbour views
Sun-loungers
The Hide With Private Wood Fired Hot Tub. A truly romantic getaway on a Vineyard
10.0 out of 10, Exceptional, (47)
"Amazing vineyard views, the hide is done out beautifully with all the pots and pans you need for indoor or outdoor hob or bbq cooking so you need to bring nothing. Wood burners in each room and a fire pit outside for cooking/ marshmallow toasting makes it so cozy! Hot tub is so much fun to heat with the wood burner and so relaxing to look over the vineyard sat with a glass of vino. Completely isolated and so peaceful. hosts are so friendly and helpful. We booked the vineyard tour and cheese and...
The Hide With Private Wood Fired Hot Tub. A truly romantic getaway on a Vineyard
Fridge, microwave, oven, stovetop
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
9.8 out of 10, Exceptional, (29)
"We booked the farmhouse for Easter weekend and to celebrate our mums 84th birthday. Everything was spotlessly clean when we arrived and the house was lovely and warm We had a wonderful weekend relaxing and going to the beaches nearby Highly recommend The Pymore Inn for food where we all went for mums birthday lunch The games room at the farmhouse was particularly popular with the teenagers who had a pool tournament Thank you for a memorable stay!"
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Beach
The hideaway with free parking
9.6 out of 10, Exceptional, (5)
"Georgous coach house, beautiful decor and had eveything you needed. It was very clean and just lovely. Annabelle, th host, couldnt have been more helpful. Would love to stay here again."
The hideaway with free parking
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See all available properties in Portland
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.

Other types of properties in Portland you may be interested in

View from property
Heights Hotel
3.0 star property
8.4 out of 10, Very good, (515)
"Great hub for a visit to Portland. Good food, beautiful views and the staff were extremely pleasant. Would visit again."
The price is NZ$256
includes taxes & fees
9 Jun - 10 Jun
Heights Hotel
Property grounds
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
10.0 out of 10, Exceptional, (1)
"Had a wonderful stay on this beautiful boat, extremely clean and tidy with all the amenities you could hope for. Excellent location and lovely marina to enjoy with great facilities. Will definitely be returning again very soon. Very highly recommended."
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
View from property
The Aqua
3.0 star property
7.8 out of 10, Good, (175)
"Basic hotel, Clean, welcoming, but sadly the restaurant was closed due to staff shortages. Breakfast good staff helpful. Very well located for access to the dockyard/port. Parking easy. "
The price is NZ$242
includes taxes & fees
21 May - 22 May
The Aqua
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.

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 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 garden and laundry facilities 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 25 Expedia holiday rentals in Portland for a memorable holiday.

What can I see and do in Portland?

Cultural attractions include Portland Museum and Royal Manor Theatre, 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.

Recent reviews of Portland properties
Expedia verified reviews