Portland Vacation Rentals

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Vacation Rentals in Portland

Vacation Home in Fortuneswell

9.4 out of 10, Exceptional, (23)
"This is the second year that we've stayed here and will continue to book in the futue. It is a beautiful accommodation, local to amenities and in walking distance to the beach.I couldn't recommend this property and Alison high enough."
United Kingdom
Rosemarie D.
Beautiful, family friendly Cottage with sea views of Chesil Beach

Apartment in Weymouth

9.2 out of 10, Wonderful, (31)
"Comfortable apartment with just a short walk to the beach and the centre of Weymouth."
United Kingdom
sue p.
Apartment near the beach with private parking and pet friendly

Cottage in West Milton

9.8 out of 10, Exceptional, (86)
"Comfortable accommodation in a superb location."
United Kingdom
Amanda S.
Buckingham Cottage : Idyllic Getaway Cottage in the rolling hills of Dorset

Cottage in Maiden Newton

9.6 out of 10, Exceptional, (46)
"A lovely relaxed stay, nice peaceful area, plenty of places to walk, highly recommend gor a bit of r&r."
United Kingdom
Spencer C.
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

Aparthotel in Wareham

4.0 star property
9.8 out of 10, Exceptional, (44)
"PRPOERTY VERY SPACIOUS, VERY CLEAN AND JUST A LOVELY PROPERTY TO UNWIND AND RELAX WITH FAMILY, LOVED THE SAUNA"
United Kingdom
tina
The Dorset Resort

Vacation Home in Wyke Regis

10.0 out of 10, Exceptional, (109)
"Lovely Cottage for a Great vacation. "
Germany
Victoria Sylvia H.
Quiet location, short walk to beach, with views of Portland and Jurassic coast

Cottage in Weymouth

2.5 star property
$436 nightly
The price is $524
Dec 9 - Dec 10
Total with taxes and fees
18 Chamberlaine Road

Cottage in Bridport

10.0 out of 10, Exceptional, (2)
"Lovely place to stay! Really great location too - would come back for sure!"
United Kingdom
Ru P.
A beautiful comfortable cottage in the centre of Bridport.

Cottage in Bridport

10.0 out of 10, Exceptional, (71)
"Lovely cottage, perfect location Will definitely try to go again at some point "
United Kingdom
Peter L.
Characterful 18th century cottage in Bridport close to the Jurassic Coast.

Cottage in Weymouth

3.0 star property
Leo's Place

Vacation Home in Langton Matravers

9.4 out of 10, Exceptional, (69)
"Lovely cottage we all had a great stay"
United Kingdom
Pat H.
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight

Cottage in Wareham

3.5 star property
The Studio - Arne

Mobile Home in Weymouth

9.8 out of 10, Exceptional, (124)
"Very clean, great communication, amazing views."
United Kingdom
Neil
Luxury mobile home with spectacular sea views.

Vacation Home in Abbotsbury

10.0 out of 10, Exceptional, (68)
"Greenbanks is outstanding and most definitely 5 starLocation is superb , the house was impeccable , we thoroughly enjoyed our stay and will hopefully visit again "
United Kingdom
Anonymous traveler
Private detached cottage to rent on Chesil Beach

Residence in Dorchester

2.0 star property
$926 nightly
The price is $1,111
Dec 10 - Dec 11
Total with taxes and fees
4 Bed-2 Bath-bar-pool Table-library- Xmas Venue

Apartment in Weymouth

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

Vacation Home in Weymouth

8.8 out of 10, Excellent, (45)
"A lovely stay in Weymouth. Minutes to the beach and the train station. Harbour within 15 minutes. Downstairs space amazing . "
United Kingdom
Gemma K.
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Cabin in Dorchester

2.0 star property
Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake

Cottage in West Knighton, nr Dorchester, Dorset

9.8 out of 10, Exceptional, (53)
"Cracking property very well equipped, excellent all round cottage, lovely setting."
United Kingdom
Robert F.
Delightful thatched cottage in beautiful sleepy Dorset village and countryside

Vacation Home in Weymouth

10.0 out of 10, Exceptional, (51)
"Outstanding house in ideal location. I could have sat in the garden all week!"
United Kingdom
Robert G.
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
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 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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Portland in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $524 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 private yard, and a barbecue grill 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 18 Expedia vacation rentals in Portland for a memorable vacation.

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 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.