Holiday Rentals in Portland

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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
Outdoor dining
Large Seaside House near WPNSA and beach. Sunset views from house and garden.
10.0 out of 10, Exceptional, (1)
"Very easy to rent and run,"
Large Seaside House near WPNSA and beach. Sunset views from house and garden.
Beach nearby, sun-loungers
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
10.0 out of 10, Exceptional, (74)
"Lovely cottage clean and welcoming. Everything you need like home from home. Well placed for visiting different places. Great view of the coastline. Great if your a walker or cylist have the Rodwell Trail on your doorstep."
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Beach nearby
Luxury mobile home with spectacular sea views.
9.8 out of 10, Exceptional, (97)
"Firstly the host, Neill, is quick to respond to questions, helpful and welcoming. The booking and checking in process was very straightforward. The mobile home itself was spacious and very well thought out - more storage than others we’ve stayed in, especially in the bathroom (although a couple of hooks for towels would be helpful). All basics are provided and some extras (tea towels, washing up liquid, bedding) wifi was very good. The view of the marina is lovely and the location is a great...
Luxury mobile home with spectacular sea views.
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.
Exterior
Delightful thatched cottage in beautiful sleepy Dorset village and countryside
9.8 out of 10, Exceptional, (41)
"We (7 adults, 2 children and 1 dog) had a lovely New Year break in this cottage. The location is great (with the pub next door) and the village itself and nice and quiet.The cottage has everything you need and more!"
Delightful thatched cottage in beautiful sleepy Dorset village and countryside
Property grounds
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
9.6 out of 10, Exceptional, (107)
"Warm welcome on arrival. The accommodation was very clean and well stocked . Very comfortable stay ."
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
Spacious Coastal House with Panoramic Sea Views Nr Sea & Sandy Beaches
10.0 out of 10, Exceptional, (80)
"Loved the quiet beauty of the place."
Spacious Coastal House with Panoramic Sea Views Nr Sea & Sandy Beaches
Interior
Beachside, stunning apartment with sea and harbour views
9.8 out of 10, Exceptional, (50)
"Very clean and well equipped. Great location, stunning views. Will be back and will also recommend to others."
Beachside, stunning apartment with sea and harbour views
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)
Fridge, microwave, oven, stovetop
Apartment near the beach with private parking and pet friendly
9.4 out of 10, Exceptional, (13)
"Nice little apartment with everything you need host was very informative about the property and in a nice little quiet location 5 mins walk way from the beach would recommend to anyone staying there!!"
Apartment near the beach with private parking and pet friendly
Interior
Peacehaven Retreat - 4 minutes from the beach!
10.0 out of 10, Exceptional, (1)
"The apartment was a peaceful haven for us to stay in! Small but cosy, amazing to have a Comfortable bed/sofa bed, tv and coffee machine. It was great to meet the host as soon as we made contact when we needed help- they were very attentive! We found free street parking near by, only 5 minute walk away. The location was very close to the beach /shops so very convenient for our short stay. Thank you for all the homely touches which made the most of the space such as plants and the decor was really...
Peacehaven Retreat - 4 minutes from the beach!
Fridge, microwave, oven, stovetop
Thatched Mid Terraced Cottage
8.0 out of 10, Very good, (3)
"Nice property but very moldy inside. When my son entered he began counting spiders. He stopped at 15 but estimated that there must’ve been 30 spiders in the stairwell and main hallway. Now I like spiders and would never kill one, but I realize that’s not for everyone. I would trap them and put them outside. There was no WiFi. Zero, we connected to the router but that had no connection to the Internet. Also there was very limited cell phone service, so mobile hotspot was spotty. We were...
Thatched Mid Terraced Cottage
Beach
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
9.6 out of 10, Exceptional, (55)
"Such a lovely comfortable and cosy cottage with fabulous views. It's in a beautiful location with so many sea and country walks all around. John and Diana were very welcoming and wonderful hosts. We couldn't have been happier there."
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Property grounds
escape the ordinary - private self catered group holiday stay
10.0 out of 10, Exceptional, (1)
"We had a lovely long weekend at the Piddle Inn. Downstairs is just like a pub - all for us! Bar, games room and pub kitchen fantastic for a family group. Gorgeous bedrooms and the sound of the stream at night. Lovely walks straight from the back and Alan the host, was incredibly helpful and friendly."
escape the ordinary - private self catered group holiday stay
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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

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
Heights Hotel
3.0 star property
8.4 out of 10, Very good, (507)
"View from the bedroom. Over looking car park."
The price is €144
per night
2 Jun - 3 Jun
Heights Hotel
Rooftop terrace
The new Admiralty Hotel
3.5 star property
8.0 out of 10, Very good, (625)
"When one drives up first impressions are "oh dear". But keeping an open mind it's a gem of a hotel. The building is ex military on a very exposed elevated position. Every member of staff was incredibly helpful and engaging. The room was comfortable and clean. Good was pretty good too and not too expensive. "
The new Admiralty Hotel
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.

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 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 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

The Manor House

The Manor House

5/5 Excellent
"lovely location"
A verified traveller stayed at The Manor House
Posted 2 days ago
The Manor House