Portland Vacation Rentals

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Vacation Rentals in Portland

Beautiful, family friendly Cottage with sea views of Chesil Beach

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

The View

2.5 star property
Portland
$840 nightly
The price is $1,008
Nov 14 - Nov 15
Total with taxes and fees
The View

The Dorset Resort

4.0 star property
Wareham
9.8 out of 10, Exceptional, (44)
"Wonderful "
United Kingdom
sarah
The Dorset Resort

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

Maiden Newton
9.6 out of 10, Exceptional, (45)
"Lovely airy cottage - exactly as it looks on the website.Perfect for a quiet retreat."
United Kingdom
Roger A.
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

Luxury mobile home with spectacular sea views.

Weymouth
9.8 out of 10, Exceptional, (123)
"Good well maintained caravan, very clean and a very nice outlook from nice balcony. "
United Kingdom
Craig W.
Luxury mobile home with spectacular sea views.

Private detached cottage to rent on Chesil Beach

Abbotsbury
10.0 out of 10, Exceptional, (68)
"Beautiful property, well equipped with all amenities, very cosy and comfortable. The highlight was the location and if you looking to get away from it all, this is the perfect place."
United States
David Walker & B.
Private detached cottage to rent on Chesil Beach

Quiet location, short walk to beach, with views of Portland and Jurassic coast

Wyke Regis
10.0 out of 10, Exceptional, (109)
"Lovely property, quiet location, very well equipped exactly what I wanted."
United Kingdom
Jennie N.
Quiet location, short walk to beach, with views of Portland and Jurassic coast

18 Chamberlaine Road

2.5 star property
Weymouth
$434 nightly
The price is $521
Nov 14 - Nov 15
Total with taxes and fees
18 Chamberlaine Road

The Studio - Arne

3.5 star property
Wareham
$1,506 nightly
The price is $1,807
Nov 14 - Nov 15
Total with taxes and fees
The Studio - Arne

Charming Country Retreat on Old Sherbourne Road

Dorchester
9.0 out of 10, Wonderful, (2)
"A lovely little cabin hidden away for a break away, and a place to reset, So close to the beach and Weymouth town too was also a plus. thank you to Tracy the lovely host who made us feel so welcome."
United Kingdom
Suzie E.
Charming Country Retreat on Old Sherbourne Road

Apartment near the beach with private parking and pet friendly

Weymouth
9.0 out of 10, Wonderful, (30)
"Lovely flat, spotlessly clean. Good central location. Good facilities, only 2minor things, the shower head needed descaling as the holes were mainly blocked, and the 2hand basins did not hold water it kept draining out. Otherwise a brilliant place to stay for a week in Weymouth. "
United Kingdom
elaine g.
Apartment near the beach with private parking and pet friendly

Leo's Place

3.0 star property
Weymouth
$699 nightly
The price is $838
Nov 14 - Nov 15
Total with taxes and fees
Leo's Place

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

2.0 star property
Dorchester
$327 nightly
The price is $393
Dec 1 - Dec 2
Total with taxes and fees
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly

Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight

Langton Matravers
9.4 out of 10, Exceptional, (68)
"Lovely old cottage in a peaceful setting with wonderful countryside views. Great walks directly from the cottage and easy access to local places of interest. "
United Kingdom
Alison K.
Purbeck cottage near Swanage & Studland - views of Corfe and I of Wight

Ocean Swell

3.5 star property
Weymouth
$688 nightly
The price is $825
Nov 13 - Nov 14
Total with taxes and fees
Ocean Swell

Upwey - Wessex Quarters

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

Historical, Characterful, Converted Old School House

Lower Bockhampton
9.0 out of 10, Wonderful, (2)
"Very nice clean well furnished"
United States
Stephen Z.
Historical, Characterful, Converted Old School House

Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Weymouth
8.8 out of 10, Excellent, (45)
"This property is in need of some tlc. If you are using the loft room it has wooden steep stairs and no handrail at all which made it extremely difficult to access. There is NO on site parking as advertised in fact there is NO parking near the property at all. Had to park some streets away which were not permit parking like outside the property, this caused friction with the owners of the house that we parked in front of which we ended up getting verbally abused for. Kettle was dirty and needed...
United Kingdom
Keith
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake

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

Beautiful large Georgian house with a big garden. Perfect for a family or two!

Wareham
10.0 out of 10, Exceptional, (73)
"Excellent facilities, lovely garden, close to shops and easy to get to."
United Kingdom
Jennifer P.
Beautiful large Georgian house with a big garden. Perfect for a family or two!
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 $393 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 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.