Portland Vacation Rentals, England: house rentals & more

Select from 17 homes, 84 cottages, and other vacation rentals in Portland to find one that's perfect for your trip. Whether you’re traveling with friends, family, or just with your pet, vacation homes have the amenities you expect for your stay, which might include WiFi and a hot tub. You'll be sure to find a rental for everyone's needs, including options that are accessible or non-smoking.

Vacation rentals with weekly discounts - Portland

Showing deals for:Oct 17 - Oct 24

‘The Hide’: A Shepherd’s Hut with a Wood fired hot tub and fire pit

Exceptional

(52 reviews)

The Hide With Private Wood Fired Hot Tub. A truly romantic getaway on a Vineyard

Weymouth, England

9% off

Fees included upfront

Alpaca Cottage is attached to the owner's house, but completely self contained

Exceptional

(142 reviews)

Beautifully appointed west Dorset Cottage With Open Parkland Views

Dorchester, Dorset

9% off

Fees included upfront

Exceptional

(97 reviews)

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

Weymouth, England

9% off

Fees included upfront

Exceptional

(17 reviews)

No.26 Marina View apartment, parking permit, harbour and Marina views

Weymouth, England

5% off

Fees included upfront

Exceptional

(17 reviews)

Family Cottage close to beach ,town ,pub restaurants, coach & rail links

Weymouth, ENG

9% off

Fees included upfront

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Portland

Portland Bill Lighthouse

Find the best place to stay - Portland

Beautiful, family friendly Cottage with sea views of Chesil Beach

Sleeps 4 · 3 bedrooms · 1 bathroom

Top rated rentals - Portland

Living room | Freshwater Bay View, Portland

Premier Host

Could not fault this annex accommodated, spotless, warm, and inviting.

Could not fault this annex accommodated, spotless, warm, and inviting. We always cook, holiday or not and for us a couple more dishes,ie, casserole, etc., would have been helpful. Overall a fantastic stay.

Christine Proud

Stayed Jun 2025

Premier Host

Wow.

Wow.... what can I say....It's a fantastic location with fab views and the peace & quiet is outstanding. The property is everything you need including the added binoculars to check out the views and the birds of prey in the area.The hot tub is an added bonus, giving you again peace whilst you can watch the world go by....absolutely spot on!!Mandy, the owner is always on hand for any questions or concerns..I would highly recommend this venue 100%.

Kirstie Kirk

Stayed Jun 2025

Wonderful Weekend Stay - Highly Recommend!

We recently spent a delightful weekend at Lisa's place, and it was a fantastic experience from start to finish. Lisa, was incredibly helpful and attentive, ensuring that our stay was as smooth and enjoyable as possible. The property was exactly as described—very spacious and immaculately presented. It comfortably accommodated my wife and I, and our three children (aged 13, 11, and 5). The space was thoughtfully arranged and beautifully decorated, providing a welcoming and comfortable atmosphere. Everything we could possibly want was provided. The kitchen was well-equipped, the bedrooms were cozy, and the living areas were perfect for family time, with sky TV so we didn't miss any of the Olympics! Overall, it was such a lovely place to stay, and we had a truly memorable time. Thank you, Lisa, for being such a wonderful host and making our weekend getaway so enjoyable. We highly recommend this property to anyone looking for a perfect holiday experience!

Russell H.

Stayed Aug 2024

Penn Castle = Amazing & Magical

I booked this for my 40th birthday and Post-wedding celebration, and the entire experience was a fairytale. The views of the Jurassic coast that the castle sits upon are breathtaking. The castle itself is a perfect size, just enough to get a little lost in. The management team (Tessa and Hannah) are great. I couldn't have asked for a better experience.

Trena T.

Stayed May 2023

Open plan kitchen, living and dining room equipped with a Smart TV with Netflix.

Perfect for Exploring

This is a really lovely house perfectly located for exploring both Portland and Weymouth. The house is very well equipped with plenty of space for 8 and a private garden. The area is peaceful and the property is close to Chesil Beach and a ideal spot for beautiful sunsets. Thank you for a terrific stay, we loved it.

Caroline T.

Stayed Jul 2020

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A place for everyone
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Find out more about Portland

The friendly city of Portland awaits you

Enjoy the history and other features of Portland. Travelers to this welcoming city praise the sailing, bars and windsurfing. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Portland

Are you hoping to find top things to see and do while you're in town? Venture out of your vacation home and experience everything that makes Portland a fun place to get away. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city center:

SEA LIFE Centre Weymouth (5.6 mi / 9 km)
Abbotsbury Swannery (10.6 mi / 17 km)
Monkey World Ape Rescue Center (14.1 mi / 22.7 km)
Warmwell Holiday Park Ski Slope (10.7 mi / 17.2 km)
The Blue Pool and Tea House (16.6 mi / 26.7 km)
Pirate Adventure Mini Golf (5.7 mi / 9.1 km)

Exploring the natural features in Portland

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Portland is a great place to get out in nature. Here are some of the area’s most eye-catching sights, all within 30 miles (48.2 km) of the city center:

Durdle Door (8.7 mi / 14 km)
Portland Bill (2.1 mi / 3.3 km)
Chesil Beach (2.8 mi / 4.5 km)
Weymouth Harbour (4.5 mi / 7.2 km)
Weymouth Bay (4.5 mi / 7.2 km)
Weymouth Beach (4.6 mi / 7.4 km)

Traveling to and around Portland

The nearest airport is in Bournemouth (BOH-Bournemouth Intl.), located 30.9 mi (49.7 km) from the city center.

Frequently asked questions

What is the best area to stay in Portland when booking a vacation rental?

If you're heading to Portland, Southwell is considered one of the most desired locations to book a vacation rental. While you're here, keep busy by touring fantastic attractions like Church Ope Cove and Portland Museum.

What is the most popular type of vacation rental accommodation in Portland?

Cottages are the most popular kind of vacation rental in Portland, according to our data. Even if you've got a different idea about what you'd like, Vrbo has properties in many shapes and sizes. Take a look at our options to find your perfect Portland pad.

How much does it cost to rent a vacation rental in Portland?

The average price for a vacation home in Portland depends on a number of factors, including property type, season and length of stay. Whether you're looking for a villa with space for extended family or a quaint cabin ideal for just you and the kids, just enter your dates of travel to discover stays with great value.

How much does it cost to rent a beach house in Portland?

The average price for a vacation rental by the beach in Portland depends on when you'll be there and the size and type of property you're looking for. Find prices easily on Vrbo by entering your travel dates and destination. Then use the handy filters to pick the number of bedrooms and amenities that you prefer, such as air conditioning, WiFi and a pool.

Are there pet-friendly vacation rentals in Portland?

You're in luck! There are. You can pick from 91 vacation rentals that cater to pets in Portland. Lots of our pet-friendly vacation rentals have an outdoor area for your four-legged pal to play in, dog beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect vacation home on Vrbo.

Can I rent a house with a pool in Portland?

Add a whole new level of fun to your vacation by booking your family into one of the 13 houses with a private pool in Portland. Use our search filter to find the kind of property you want on Vrbo, and then spend your days splashing and playing in a swimming pool that's just for you.

What are popular rental amenities in Portland?

When it comes to rental amenities that people are looking for in Portland, an ocean view, a beach view and a water view rank the highest. With Vrbo vacation rentals, there are options to fit your style and taste, whether you're vacationing with relatives, friends or even pets.

Are there large group vacation rentals in Portland?

You can pick from four vacation properties in Portland that can accommodate a group of 10 or more guests. Whether you're planning a get-together with extended family or an event like a party, there's enough space to get your group together under the same roof.

Are there vacation rentals in Portland that welcome kids?

Gather your whole family for an adventure in Portland at one of our 90 family-friendly vacation homes. Many of these stays offer conveniences that are just perfect for trips with children, including laundries, extra bedrooms and pools. Just click on the "Properties good for families" filter box and decide on your favorite.

What are the top attractions for families in Portland?

Keeping the kiddos entertained during your stay in Portland is a breeze with these cool family-friendly attractions:

Portland Bill Lighthouse
Weymouth and Portland National Sailing Academy
Portland Castle

Are there one-bedroom vacation rentals in Portland?

Yes, you'll find 11 one-bedroom properties in Portland to choose from. A one-bedroom vacation rental is a great choice if it's just two of you or if you're vacationing alone. Throw in more space, privacy and convenience compared to a regular hotel, and you've got yourself an unforgettable trip.

Can I find two-bedroom vacation rentals in Portland?

You can pick from 30 two-bedroom vacation rentals in Portland. Settle the kids into the second room or fill it with a couple of your best buddies. There's plenty of space for whoever's lucky enough to come along for the ride.

Are there vacation rentals with WiFi in Portland?

You'll find 18 vacation rentals with WiFi in Portland. If you'd like to disconnect from the world during your trip, but still need to be connected to the web, these getaways are for you. Narrow your search by applying the WiFi filter on Vrbo.

How can I find vacation rentals with air conditioning in Portland?

Portland has four vacation rentals where you can relax in air-conditioned comfort. To locate a property on Vrbo featuring this amenity, enter your desired travel dates and use the handy filters to select the "air conditioning" box.

How old do you have to be to rent a vacation rental in Portland?

It's advisable to check with the Portland vacation home you want on Vrbo as age restrictions vary. However, it's generally 16, 18 or 21.

How long can I rent a vacation rental in Portland for?

The length of time you can book a vacation rental in Portland is down to the property. Just enter your preferred travel dates to view a list of options offering extended stays. With tons of creature comforts such as washing machines and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find a perfect place to call your home away from home in Portland.

Does Vrbo offer discounts for vacation homes in Portland?

Whether you've got your eye on one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you're sure to score some amazing deals and discounts on Vrbo. From mini stays to extended getaways, we've got the ideal space for your next Portland escape.