Portland Vacation Rentals from $493: Search Short-Term Rentals

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In two weeks

In two months

In three months

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Our top choices for Portland vacation rentals

Cottage in Portland

Trevor

$591 nightly

Jan 22 - Jan 23

Total with taxes and fees

Cottage in Portland

$705 nightly

Jan 20 - Jan 21

Total with taxes and fees

Cottage in Portland

$556 nightly

Jan 22 - Jan 23

Total with taxes and fees

Cottage in Portland

$532 nightly

Jan 20 - Jan 21

Total with taxes and fees

Cottage in Portland

$525 nightly

Jan 22 - Jan 23

Total with taxes and fees

Cottage in Portland

$591 nightly

Jan 20 - Jan 21

Total with taxes and fees

Cottage in Portland

$746 nightly

Feb 6 - Feb 7

Total with taxes and fees

Cottage in Portland

$690 nightly

Jan 20 - Jan 21

Total with taxes and fees

Cottage in Portland

$667 nightly

Jan 22 - Jan 23

Total with taxes and fees

Cottage in Portland

"Nice size property. Missing the more luxury/comfort items. Garden furniture ok not as images. Has a comfy dining table. Balcony furniture present but not suitable for the area. High stools and table not appropriate needs more relaxing items to make area useful otherwise it was good for drying clothes. Area is central and easy for amenities, cafes, beach, shops etc all easy to walk to. Noisy as near heliport and some days this is busy from early morning till after 10 at night. Not overly...

Michelle

$1,150 nightly

Jan 23 - Jan 24

Total with taxes and fees

Cottage in Portland

$638 nightly

Jan 30 - Jan 31

Total with taxes and fees

Cottage in Portland

$800 nightly

Jan 20 - Jan 21

Total with taxes and fees

Cottage in Portland

$1,078 nightly

Jan 22 - Jan 23

Total with taxes and fees

Cottage in Portland

$895 nightly

Jan 22 - Jan 23

Total with taxes and fees

Vacation Home in Portland

$1,375 nightly

Jan 20 - Jan 21

Total with taxes and fees

Vacation Home in Wool

Angel F.

$360 nightly

Jan 29 - Jan 30

Total with taxes and fees

Apartment in Weymouth

Louise P.

$153 nightly

Jan 19 - Jan 20

Total with taxes and fees

2 bedrooms, desk, iron/ironing board, free WiFi

Vacation Home in Dorchester

Carol S.

$225 nightly

Jan 19 - Jan 20

Total with taxes and fees

Cottage in Weymouth

M A

$596 nightly

Jan 20 - Jan 21

Total with taxes and fees

Vacation Home in Wool

$282 nightly

Jan 17 - Jan 18

Total with taxes and fees

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Top Portland Hotel Reviews

Kingston Country Courtyard

10/10 Excellent

"Wonderful place, lovely clean room with full kingsize bed (not 2 singles), nice big shower and wonderful staff"

Durdle Door Hotel

10/10 Excellent

"A lovely winter break in a perfect location. Staff went above and beyond to accomodate our requests during our stay, an extended family get together for a special birthday (8 people). We had four rooms for our family, good sized family room with double, single and sofa bed with nice sea peek; a twin with sea views; and two doubles, one sea view side. The hotel is a brick historic Victorian country house hotel set in a great elevated position in West Lulworth, a short stroll up from the cove. Rooms in the house are cosy and clean with modern decor and bathrooms. We all found the beds and pillows very comfortable and had a great sleep, despite the wild weather outside! There is a lovely spacious contemporary lounge/dining space which was great for our family to hang out together, with board games and bar. The hotel doesn't do full restaurant any more since change of ownership, they offer pizzas and I think a few bar snack type choices which we didn't try as we ate out locally. The continental breakfast was good, an optional extra, which is a buffet with pastries, pancakes, toast, cereals, yoghurt, fresh fruit, cheese, cold meats, good coffee in the lovely large orangery dining space which has beautiful views. Parking permits can be arranged via a code from the hotel for the main Lulworth car park with a small parking area at the hotel for unloading on arrival. A perfect January stay in a beautiful location. Reasonable value rooms. We would stay here again. "

The Smugglers Inn

10/10 Excellent

"Really warm welcome at the hotel, taken to our room which was very clean cosy and snuggly. Amenities in the room excellent and we were catered for well, including sufficient space for the dogs. Ate two nights in the bar/restaurant, staff very good, food lovely, excellent selection for gluten free which was amazing to experience. A lovely restful couple of days and made To feel exceptionally welcome "

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 $493 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.

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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 16 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.

Portland Vacation Rentals

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Check prices for these dates

Our top choices for Portland vacation rentals

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Cottage in Portland

Vacation Home in Portland

Vacation Home in Wool

Apartment in Weymouth

Vacation Home in Dorchester

Cottage in Weymouth

Vacation Home in Wool

Find vacation rentals that suit your style

Top Portland Hotel Reviews

Kingston Country Courtyard

Find out more about Portland

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