Portland Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Portland

Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
Property grounds
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
10.0 out of 10, Exceptional, 1 review
"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.
Beautiful, family friendly Cottage with sea views of Chesil Beach
Exterior
Beautiful, family friendly Cottage with sea views of Chesil Beach
9.6 out of 10, Exceptional, 14 reviews
"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
Entire home hosted by Lisa
Exterior
Entire home hosted by Lisa
10.0 out of 10, Exceptional, 9 reviews
"This is our second stay at this home and it was just as lovely. The location next to church Ope beach is wonderful; Lisa is an excellent host; and the house is homely, stylish and well-equipped. We loved it!"
Entire home hosted by Lisa
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Two Bedroomed Bungalow at Cove Holiday Park
Living area
Two Bedroomed Bungalow at Cove Holiday Park
9.8 out of 10, Exceptional, 73 reviews
"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
Charming Sea View Cottage in Portland Dorset
Property grounds
Charming Sea View Cottage in Portland Dorset
10.0 out of 10, Exceptional, 1 review
"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
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
Property grounds
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
9.6 out of 10, Exceptional, 109 reviews
"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
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, 15 reviews
"Ideal little holiday apartment."
Apartment near the beach with private parking and pet friendly
Gorgeous Georgian Home
Outdoor dining
Gorgeous Georgian Home
Gorgeous Georgian Home
Luxury mobile home with spectacular sea views.
Beach nearby
Luxury mobile home with spectacular sea views.
9.8 out of 10, Exceptional, 99 reviews
"Very pleasant"
Luxury mobile home with spectacular sea views.
No.26 Marina View apartment, parking permit, harbour and Marina views
View from property
No.26 Marina View apartment, parking permit, harbour and Marina views
10.0 out of 10, Exceptional, 6 reviews
"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
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
Fridge, microwave, oven, stovetop
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
9.4 out of 10, Exceptional, 16 reviews
"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
The Hide With Private Wood Fired Hot Tub. A truly romantic getaway on a Vineyard
Sun loungers
The Hide With Private Wood Fired Hot Tub. A truly romantic getaway on a Vineyard
10.0 out of 10, Exceptional, 47 reviews
"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
The Dorset Resort
Signature Chalet, 3 Bedrooms, Accessible, Sauna
The Dorset Resort
4.0 star property
10.0 out of 10, Exceptional, 22 reviews
"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
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
9.6 out of 10, Exceptional, 57 reviews
"We had a wonderful long weekend staying in this delightful little cottage. The views are spectacular- you can see Corte castle & the sea from the front room & master bedroom. Perfect location for exploring Swanage, Studland & surrounding Dorset countryside. The cottage is really well equipped, very clean & comfy. Parking was easy & for anyone with an EV there are 4 charging points in the main Swanage car park! John was super helpful & replied quickly to any questions we had. Highly recommend!"
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Fridge, microwave, oven, stovetop
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
9.8 out of 10, Exceptional, 30 reviews
"This is probably the very best holiday accommodation i have ever stayed in. It was clean, spacious and the kitchen was superbly well equipped. The grounds are extensive, wirh beautiful views. We were here in late spring when rhe blossom and birdsong are amazing. We had an age range of 9 to 70 and everybody was happy. The games room got a lot of use! The hosts were pleasant and gracious. A very very big thank you to our hosts. Worth every penny!,"
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Stunning 1-bedroom coach house with free parking
Beach
Stunning 1-bedroom coach house with free parking
9.6 out of 10, Exceptional, 5 reviews
"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."
Stunning 1-bedroom coach house with free parking
Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset
Fridge, microwave, oven, stovetop
Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset
10.0 out of 10, Exceptional, 72 reviews
"Very easy to find great location for walking also local pubs very very quiet great place to put your feet up and relax also the garden is great too."
Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Beach nearby, sun loungers
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
10.0 out of 10, Exceptional, 75 reviews
"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
Luxury Detached House and Grounds, also benefits from full disabled facilities.
Fridge, microwave, oven, stovetop
Luxury Detached House and Grounds, also benefits from full disabled facilities.
9.4 out of 10, Exceptional, 65 reviews
"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.
Weymouth, Dorset - Pebble Bank with stunning views of Chesil Beach
Bar (on property)
Weymouth, Dorset - Pebble Bank with stunning views of Chesil Beach
9.4 out of 10, Exceptional, 20 reviews
"Very nice"
Weymouth, Dorset - Pebble Bank with stunning views of Chesil Beach
Don't see what you're looking for?
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.

Portland Vacation Rental Travel Info

Number of vacation rentals
78
Popular accommodation
Portland cottages
Known landmarks
Weymouth Beach, Chesil Beach and Weymouth Pavilion
International airport
London (LHR-Heathrow)

Other types of properties in Portland you may be interested in

Heights Hotel
View from property
Heights Hotel
3.0 star property
8.4 out of 10, Very good, 529 reviews
"No real issues with the Hotel, it's a little dated in places, but comfortable and the breakfast was good. The view from the Bistro / Bar is amazing. Our room (220) suffered a little from road noise but was otherwise fine. The curtains definitely need to go back to the eighties though!"
The price is CA $189
CA $227 total
includes taxes & fees
Jun 16 - Jun 17
Heights Hotel
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
Property grounds
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
10.0 out of 10, Exceptional, 1 review
"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.
The Aqua
View from property
The Aqua
3.0 star property
7.8 out of 10, Good, 175 reviews
"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 CA $164
CA $197 total
includes taxes & fees
Jun 19 - Jun 20
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.

Everything you need to know about Portland vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Portland vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Portland vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Portland vacation 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 vacation 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 vacation.

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 vacation rental in Portland?

Yes, you can find vacation rentals close to popular sights in Portland, or you can select a more remote option if you'd like a relaxing place to 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 vacation rentals in Portland?

Beautiful, family friendly Cottage with sea views of Chesil Beach : Visitors give good reviews to this Portland vacation home rental, which 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Portland?

Choose from 22 Expedia vacation rentals in Portland for a memorable vacation.

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 vacation rentals like in Portland?

Vacation rentals are private properties you can stay in for a couple days or more in Portland. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of privacy away from public hotel elevators and busy front desks while still allowing you the experience of travel. You'll also get more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for family trips.

Recent reviews of Portland properties
Expedia verified reviews

Fairhaven Hotel

Fairhaven Hotel

5/5 Excellent
"We had a great stay at Fairhaven Hotel. The family room was comfortable and a good size, and the location of the hotel was perfect for direct access to the beach and other local amenitiies The staff were all very friendly and helpful, and my son loved the breakfasts! We would definitely stay again in the future."
A verified traveller stayed at Fairhaven Hotel
Posted 2 days ago
Fairhaven Hotel