Portland Vacation Rentals

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Vacation Rentals in Portland

Beautiful, family friendly Cottage with sea views of Chesil Beach

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

Home From Home

3.0 star property
The price is CA $711
CA $853 total
includes taxes & fees
Sep 25 - Sep 26
Home From Home

The Dorset Resort

4.0 star property
9.8 out of 10, Exceptional, (41)
"PRPOERTY VERY SPACIOUS, VERY CLEAN AND JUST A LOVELY PROPERTY TO UNWIND AND RELAX WITH FAMILY, LOVED THE SAUNA"
The Dorset Resort

Self Contained Garden Studio With Private Decked Terrace, close to town and sea

9.6 out of 10, Exceptional, (139)
"Very pleasant stay; will pass on info to other family members for when they visit Bridport. "
Self Contained Garden Studio With Private Decked Terrace, close to town and sea

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

9.6 out of 10, Exceptional, (44)
"A lovely relaxed stay, nice peaceful area, plenty of places to walk, highly recommend gor a bit of r&r."
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

Luxury mobile home with spectacular sea views.

9.8 out of 10, Exceptional, (118)
"Very clean, great communication, amazing views."
Luxury mobile home with spectacular sea views.

Apartment with stunning Sea View

9.4 out of 10, Exceptional, (56)
"Excellent location, dog friendly, hosts communication was excellent would definitely stay again"
Apartment with stunning Sea View

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

10.0 out of 10, Exceptional, (49)
"This is our second visit to Blue Horizon. Another fantastic stay, felt like coming home. Love the addition of the summer room, especially great on a rainy day. Lots of walking routes directly from the property. We explored Portland, the quarry park, walking to Portland Bill along the coastal path. Highly recommend a stay at this beautiful property."
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

Luxury Pine Wood Lodge, situated in beautiful Dorset Countryside,attractions nr

9.2 out of 10, Wonderful, (88)
"We had a very restful stay on a quiet site with lovely views."
Luxury Pine Wood Lodge, situated in beautiful Dorset Countryside,attractions nr

18 Chamberlaine Road

2.5 star property
The price is CA $617
CA $740 total
includes taxes & fees
Sep 19 - Sep 20
18 Chamberlaine Road

Apartment near the beach with private parking and pet friendly

9.2 out of 10, Wonderful, (29)
"Ideal little holiday apartment."
Apartment near the beach with private parking and pet friendly

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

2.0 star property
The price is CA $385
CA $597 total
includes taxes & fees
Sep 11 - Sep 12
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly

Dorchester Nook

8.8 out of 10, Excellent, (5)
"The en-suite room in Fiona's home was perfect for our short stay. The bed and pillows were very comfortable and we had a lovely peaceful sleep. The shower was really powerful, nice big bath towels and shampoo, conditioner and body wash were provided. The location was great for us to visit Weymouth and Durdle Door. Thanks for having us!"
The price is CA $122
CA $161 total
includes taxes & fees
Sep 11 - Sep 12
Dorchester Nook

Luxury coastal property with private indoor pool.

10.0 out of 10, Exceptional, (10)
"The property is done up to a really high standard and was ideal for our group. Great Facilities, kids had a blast Location is fabulous"
Luxury coastal property with private indoor pool.

Private detached cottage to rent on Chesil Beach

10.0 out of 10, Exceptional, (68)
"It was once again a perfect stay."
Private detached cottage to rent on Chesil Beach

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

10.0 out of 10, Exceptional, (2)
"A wonderful experience - THANK YOU!"
The price is CA $168
CA $507 total
includes taxes & fees
Sep 28 - Sep 29
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Hide-a-way

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is CA $527
CA $632 total
includes taxes & fees
Sep 19 - Sep 20
Hide-a-way

Charming Country Retreat on Old Sherbourne Road

8.0 out of 10, Very good, (1)
"A small cottage with a lovely terrace in the countryside above the road at the edge of a field. Very sustainably run and beautifully furnished. A short walk to town and the beach.Tracy is a very pleasant host."
Charming Country Retreat on Old Sherbourne Road

Delightful thatched cottage in beautiful sleepy Dorset village and countryside

9.8 out of 10, Exceptional, (51)
"Beautiful historic cottage,well equipped"
Delightful thatched cottage in beautiful sleepy Dorset village and countryside

Hidden Retreat - 4 mins to beach & 3 mins to train station. Pet friendly!

8.0 out of 10, Very good, (7)
"We enjoyed staying in, the property is closed to the rail station. Probably 10 min walk from the property to the beach. "
Hidden Retreat - 4 mins to beach & 3 mins to train station. Pet friendly!
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

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, 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 CA $122 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 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 17 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.