Portland Vacation Rentals

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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Portland vacation rentals

Interior

Mermaid Cottage

Mermaid Cottage
3.0 star property
Portland
The price is CA $770
CA $924 total
includes taxes & fees
Jun 2 - Jun 3
Mermaid Cottage
Beach nearby

Home From Home

Home From Home
3.0 star property
Portland
The price is CA $737
CA $885 total
includes taxes & fees
Jun 2 - Jun 3
Home From Home
Beach nearby

74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is CA $728
CA $873 total
includes taxes & fees
Jun 6 - Jun 7
74 Reap Lane
Dining

Coastguard View

Coastguard View
3.0 star property
Portland
The price is CA $901
CA $1,081 total
includes taxes & fees
Jun 5 - Jun 6
Coastguard View
Cottage | Property grounds

Old Higher Lighthouse Stopes Cottage

Old Higher Lighthouse Stopes Cottage
3.0 star property
Portland
The price is CA $1,148
CA $1,378 total
includes taxes & fees
Jun 16 - Jun 17
Old Higher Lighthouse Stopes Cottage
Property grounds

Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is CA $956
CA $1,147 total
includes taxes & fees
Jun 13 - Jun 14
Manhattan Beach
Cottage | Interior

The Shambles

The Shambles
3.5 star property
Portland
The price is CA $977
CA $1,172 total
includes taxes & fees
Jun 2 - Jun 3
The Shambles
Beach nearby

Anchor Cottage

Anchor Cottage
3.0 star property
Portland
The price is CA $750
CA $900 total
includes taxes & fees
Jun 20 - Jun 21
Anchor Cottage
Cottage | Dining

Lighthouse View

Lighthouse View
3.5 star property
Portland
6.0 out of 10, (1 review)
"Bed was not comfy as we had backache after second night , we turned mattress round was ok that night but the after that . The step into the shower was too high and we had to buy a step to get in it and also the floor surface was very slippy . Was ck an and tidy and overall not a bad place to stay and would recommend and return at some point "
United Kingdom
Anonymous traveller
The price is CA $441
CA $529 total
includes taxes & fees
Jun 6 - Jun 7
Lighthouse View
Property grounds

Bear's Apartment

Bear's Apartment
2.0 star property
Portland
The price is CA $884
CA $1,060 total
includes taxes & fees
Jun 20 - Jun 21
Bear's Apartment
Cottage | Beach

The View

The View
2.5 star property
Portland
The price is CA $1,240
CA $1,487 total
includes taxes & fees
Jun 5 - Jun 6
The View
Cottage | Interior

Pebbles Reach

Pebbles Reach
3.5 star property
Portland
The price is CA $1,107
CA $1,329 total
includes taxes & fees
Jun 6 - Jun 7
Pebbles Reach
Cottage | Interior

St Johns View

St Johns View
3.5 star property
Portland
The price is CA $1,348
CA $1,618 total
includes taxes & fees
Jun 6 - Jun 7
St Johns View
Cottage | Interior

Sea Gem

Sea Gem
3.5 star property
Portland
The price is CA $1,493
CA $1,792 total
includes taxes & fees
Jun 2 - Jun 3
Sea Gem
Outdoor dining

Littlesea Holiday Park - Holiday Accommodation 19270

Littlesea Holiday Park - Holiday Accommodation 19270
2.5 star property
Weymouth
The price is CA $632
CA $758 total
includes taxes & fees
Jun 6 - Jun 7
Littlesea Holiday Park - Holiday Accommodation 19270
Fireplace

Duck Cottage, Sutton Poyntz

Duck Cottage, Sutton Poyntz
Weymouth
The price is CA $1,031
CA $1,031 total
includes taxes & fees
Jun 6 - Jun 7
Duck Cottage, Sutton Poyntz
WiFi

The Halt Maiden Newton, Dorset

The Halt Maiden Newton, Dorset
Dorchester
The price is CA $607
CA $607 total
includes taxes & fees
Jun 2 - Jun 3
The Halt Maiden Newton, Dorset
Living area

Fisherman's Rest, Wyke Regis

Fisherman's Rest, Wyke Regis
Weymouth
The price is CA $1,381
CA $1,381 total
includes taxes & fees
Jun 3 - Jun 4
Fisherman's Rest, Wyke Regis
Interior

Pebbles Foxglove Way, West Bay

Pebbles Foxglove Way, West Bay
Bridport
The price is CA $1,442
CA $1,442 total
includes taxes & fees
Jun 2 - Jun 3
Pebbles Foxglove Way, West Bay
Fireplace

The Old Barn, Swanage

The Old Barn, Swanage
Swanage
10.0 out of 10, Exceptional, (2 reviews)
"The location allowed for a relaxing time. Plenty of space for the whole party. Ample parking .footpaths around the home to walk from.When the Steam railway is working a great view of the trains going pass.Swanage and many other attractions very close by so an ideal base. "
United Kingdom
Lucy N.
The price is CA $1,481
CA $1,481 total
includes taxes & fees
Jun 3 - Jun 4
The Old Barn, Swanage
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

The Frampton Arms

The Frampton Arms

10/10 Excellent
"Fantastic location and very clean. The staff were very welcoming, efficient and helpful. The location is brilliant. Very easy to explore the whole of Dorset and opposite a train station, (Moreton) if you want to use the train. There’s also a bus stop opposite. We were close to the Tank Museum, Clouds Hill and the village of Moreton has a beautiful church with stunning windows, and it’s where TE Lawrence had his funeral and he is buried close by- you can visit his grave. Excellent location for exploring. The food was good and reasonably priced- we ate there on the first evening. The only drawback was the road noise sometimes during rush hour, but this is not the fault of the owners! A lovely stay and very reasonable. We were here during a heatwave, so the aircon in the room was appreciated. There is also a co-op close by for convenience too. The breakfast was generous and included too. Staff very friendly and welcoming. The Frampton family are also historically connected to the Tolpuddle Martyrs (the family were on the wrong side of history, so this was a fun connection when we visited that area too! ) Lots to see and do and near Chesil Beach, all the Hardy bits and pieces, Cerne Abbas Giant, Dorchester, Blandford Forum, Poundbury, etc. -all easily reached by car."
Sandra 4-night trip
Posted 2 hours ago
The Frampton Arms

Find out more about Portland

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Portland?

Yes, you can find vacation rentals in Portland close to Osprey Leisure Centre, or you can select a more secluded 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. Our travelers also rate Bright & beautiful 4 bedroom house with sea views as a favorite home for rent in Portland.

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.