Portland holiday homes

We found 678 holiday rentals — enter your dates for availability

Select from 16 homes, 84 cottages and other holiday rentals in Portland to find one that's perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for spending time at your holiday home, which might include a fireplace and a washer and dryer. You'll be able to choose a property to rent that has what everyone needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Portland

Showing deals for:19 Dec - 26 Dec
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Why visit Portland

  • Stunning coastal scenery: Experience breathtaking views along Portland's rugged coastline, perfect for relaxation and exploration.
  • Historic landmarks: Discover the rich history at attractions like Portland Castle and the Portland Museum.
  • Beautiful beaches: Relax on Chesil Beach, a picturesque spot ideal for sunbathing and beachcombing.
  • Outdoor adventures: Engage in various activities such as walking, cycling, and water sports amidst stunning landscapes.
  • Charming accommodation: Stay in romantic cottages with amazing sea views for a unique and cozy experience.

Top attractions near Portland

Portland, England, is perfect for an adventurous getaway with stunning scenery and outdoor activities. Explore the local attractions, including Portland Castle, the Portland Museum, and the picturesque Portland Bill. Enjoy the beautiful beaches, like Chesil Beach, and soak in the vibrant coastal culture. Whether you're keen on history or just want to unwind by the sea, Portland has something for every traveller looking for a memorable experience.

  • Weymouth Beach: A stunning sandy beach perfect for soaking up the sun, swimming, and enjoying beach vibes. It's a great spot for families and offers a relaxed atmosphere for a day out.
  • Weymouth Harbour: A picturesque harbour that boasts beautiful scenery and a fantastic selection of cafés and shops. It's a lively area where you can watch boats and indulge in local seafood.
  • Weymouth Bay: This scenic bay provides outdoor adventures, from water sports to coastal walks. The views are breathtaking, making it an ideal spot for nature lovers and photographers alike.

Things to do recommended for couples

Looking for a romantic getaway in Portland, England? Enjoy a fun round at Pirate Adventure Mini Golf or try your hand at sailing with the Weymouth and Portland National Sailing Academy. For a lovely meal, head to Mangerton Mill, perfect for a cozy evening together.

Things to do recommended for families

Portland offers delightful family experiences like Lodmoor Country Park, perfect for relaxation, and Greenhill Beach, ideal for a seaside day out. For sports enthusiasts, The Avenue Stadium provides an exciting atmosphere for enjoying local events.

Things to do recommended for groups

Groups visiting Portland can enjoy a night out at the Weymouth Pavilion for a show, hike along the scenic South West Coast Path for adventure, or catch a flick at Cineworld Weymouth for a fun family outing, all within a short drive from Portland.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Portland

If you're planning a trip with friends, family, pets, or seeking extended stays, it's important to filter your options according to what matters most to you. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Portland with a group: Think about how many bedrooms you require, along with features like a fully equipped kitchen or outdoor areas for socialising. Thankfully, you can easily filter for these options and many more on Vrbo.
  • Traveling to Portland with young kids: Traveling with little ones can be quite the adventure. It's important to prioritise their comfort and safety, along with suitable facilities like a private swimming pool. Additionally, think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Portland: For many families, a getaway wouldn't be the same without their furry companion. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Portland: If you're in search of holiday rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include amenities like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Portland

Portland offers a stunning blend of picturesque beauty and adventure, perfect for your vacation. Explore charming romantic cottages with excellent sea views, and immerse yourself in the friendly atmosphere of the city. With plenty of outdoor activities and scenic spots, such as its stunning coastline, you'll find relaxation and excitement in equal measure. Don't miss out on the nearby towns that offer family-friendly vibes and luxurious escapes.

  • Weymouth: Situated a mere 8.0km from Portland, Weymouth is a vibrant coastal city known for its stunning outdoor scenery and adventure opportunities. The picturesque beach is a must-visit, offering a family-friendly atmosphere with golden sands and inviting waters. Visitors can enjoy a variety of activities such as theatre shows, exploring recreational areas, and indulging in local seafood. The nearby rocks provide a fantastic backdrop for scenic walks and photo opportunities, making Weymouth a perfect destination for a day of exploration.
  • South Coast: Located 9.7km from Portland, the South Coast is renowned for its breathtaking landscapes and outdoor adventures. This area offers an array of hiking trails that cater to all levels, ensuring a fulfilling experience for nature enthusiasts. The coastal paths lead to stunning views of the national park and pristine beaches, perfect for a relaxing day out. The shopping mall centre adds a touch of urban flair, providing opportunities to unwind after a day of exploration. Whether you're hiking or enjoying a leisurely stroll, the South Coast promises a memorable experience.
  • Dorchester: Approximately 17.7km away from Portland, Dorchester is a historic city that blends outdoor beauty with rich culture. Known for its recreational areas and campgrounds, Dorchester is ideal for those looking to immerse themselves in nature. The nearby beaches and rocky landscapes invite visitors to explore and enjoy stunning coastal views. With its proximity to a national park, Dorchester offers various outdoor activities that highlight the area's natural beauty, making it a fantastic stop for adventure seekers and history buffs alike.

Best time to go to Portland

If you're planning a trip to Portland, it's a good idea to check both the weather and property rates. The warmest month is August.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January44.6°F (7.0°C)Light RainMostly Cloudy
February44.4°F (6.9°C)Light RainMostly Cloudy
March46.0°F (7.8°C)Light RainMostly Cloudy
April49.1°F (9.5°C)Light RainMostly Sunny
May53.8°F (12.1°C)Light RainMostly Sunny
June58.8°F (14.9°C)Light RainMostly Sunny
July62.2°F (16.8°C)Light RainMostly Sunny
August62.4°F (16.9°C)Light RainMostly Sunny
September60.3°F (15.7°C)Light RainMostly Sunny
October56.5°F (13.6°C)Light RainMostly Cloudy
November50.9°F (10.5°C)Light RainMostly Cloudy
December47.3°F (8.5°C)Light RainMostly Cloudy

Booking with Vrbo is simple

Are you keen to save some dollars on your next adventure? It might be worth considering a bit of flexibility with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To help you find the perfect Vrbo property that suits your budget, feel free to use our filters to narrow down options by price, location, and type of holiday rental. Happy travels.

Vrbo Trips: Effortless planning

The Trip Board feature on Vrbo offers a handy way to plan your next adventure, pick up from where you last left off, or manage your travel arrangements. You can easily find the properties you've saved or booked, sorted into categories like Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply head over to: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

The friendly city of Portland awaits you

Enjoy the history and other features of Portland. Travellers to this welcoming city praise the sailing, bars and windsurfing. With a holiday 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

Do you want to discover attractions to see while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Portland a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • 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 appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Portland. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • 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)

Travelling to and around Portland

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

Frequently asked questions

What is the best area to stay in Portland when booking a holiday home?
If you're thinking about a stop in Portland, Southwell is one of the more sought-after locations to spend a getaway. While you're here, pay a visit to fantastic attractions like Portland Bill Lighthouse and Church Ope Cove.
What is the most popular type of holiday home accommodation in Portland?
Based on our data, cottages are the most desirable type of property in Portland. But of course, everyone's idea of an epic trip can differ. Bookabach has holiday homes of all shapes and sizes, and we'll help you find the perfect fit.
How much does it cost to rent a holiday home in Portland?
Length of stay, property type and time of year are some of the things that can affect the price of a holiday home. Simply enter your dates of travel to find your perfect match. From comfy cabins to sprawling luxury villas, all Bookabach holiday homes offer amazing value.
How much does it cost to rent a beach house in Portland?
When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Put in your Portland travel dates to see all your options on Bookabach. Did someone just say "private pool"? Use our filters to choose the amenities and features you need.
Are there pet-friendly holiday homes in Portland?
With 68 holiday homes that welcome four-legged guests, your furry companion can join in the fun on your Portland holiday. Use the filter tool to search our pet-friendly holiday homes and find your pawfect digs on Bookabach.
Can I rent a house with a pool in Portland?
Add an extra layer of fun to your trip by booking your crew into one of the four houses with a private pool in Portland. Use our handy search filter to find the kind of property you want on Bookabach, and then spend leisurely days frolicking in a swimming pool that's for your use only.
What are popular home amenities in Portland?
A firepit, a fireplace and a swimming pool are the most popular home amenities in Portland. Whether you're planning to travel on your own, with your significant other or a group of family members, Bookabach can help you find a holiday home that matches your tastes with a load of extras you'll love.
Are there large group holiday homes in Portland?
With 29 Portland holiday homes that can sleep five or more people, you can bring a few extra friends or family members along. Whether you're planning an informal get-together or a birthday party, we'll help you find a comfortable space to match the occasion.
Are there holiday homes in Portland that welcome kids?
Bring the entire family together for an adventure in Portland at one of our 68 family-friendly holiday homes. A lot of these stays offer conveniences that are ideal for trips with children, including full kitchens, extra bedrooms and patios. Just click on the "Properties good for families" filter and choose your favourite.
What are the top attractions for families in Portland?
Keeping the kids occupied during your Portland holiday is easy with these fabulous family-friendly attractions:

  • Weymouth Beach
  • Chesil Beach
  • SEA LIFE Centre Weymouth

Are there one-bedroom holiday homes in Portland?
Yes, Portland has seven one-bedroom homes on offer. Usually located in prime areas thanks to their compact size, a one-bedroom property is perfect if you're travelling with your partner or a buddy. And with home comforts such as air conditioning and more privacy than a standard hotel, you'll be able to chill out while exploring this amazing destination.
Can I find two-bedroom holiday homes in Portland?
Gather your nearest and dearest and relax in total privacy and comfort in one of the 25 two-bedroom holiday properties Portland has to offer.
Are there holiday homes with WiFi in Portland?
Take your pick of seven holiday homes with WiFi in Portland. If you'd like to disconnect from the world on your holiday, but still want to be connected to the internet, these properties have what you need. Narrow your search by applying the WiFi filter on Bookabach.
How old do you have to be to rent a holiday home in Portland?
The minimum required age is generally 16, 18 or 21. It can vary between properties on Bookabach, so look at the rules of your preferred Portland stay before booking your escape.
How long can I rent a holiday home in Portland for?
The amount of time you can stay in a Portland holiday home for differs depending on the property. Just tap in your preferred travel dates to see available options that offer long-term stays. They come with all you require to make your extended break more comfortable like kitchens and laundries. Some properties might also offer discounted weekly or monthly prices, so you can stay even longer for less.

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