Portland holiday homes

We found 765 holiday rentals — enter your dates for availability
Select from 20 homes, 89 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:6 Nov - 13 Nov

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Why visit Portland

  • Coastal Adventures: Enjoy rugged cliffs, pristine beaches, and scenic coastal walks, perfect for outdoor enthusiasts.
  • Historic Heritage: Discover the ancient castle and immerse yourself in Portland’s rich history.
  • Picturesque Harbour: Wander the charming harbour area and relish the coastal ambience.
  • Family Fun: Experience safe, family-friendly activities along the beautiful coastline.
  • Outdoor Escapes: Embrace the natural beauty and adventure opportunities scattered throughout the city.

Top attractions near Portland

Portland, England, is a stunning destination perfect for outdoor enthusiasts and adventure seekers. Explore its beautiful beaches, historic castle, and picturesque harbour, offering a blend of culture and scenic experiences. Whether you're soaking up the sun or enjoying a coastal walk, Portland's attractions promise a memorable holiday for families, groups, or couples alike. Embrace the natural beauty and rich heritage that this charming city has to offer.

  • Weymouth Beach: Experience a vibrant seaside vibe with golden sands and the refreshing sea breeze, perfect for a relaxed day out.
  • Weymouth Harbour: Enjoy scenic views and gentle coastal ambience at this charming harbour, ideal for a leisurely stroll.
  • Weymouth Bay: Revel in the great outdoors with panoramic coastal scenery and a mix of beach and outdoor attractions, offering a unique blend of nature and leisure.

Things to do recommended for couples

For a romantic getaway in Portland, explore the stunning coastal paths with breathtaking views. Enjoy a leisurely picnic at the scenic Portland Bill, or take a sunset stroll along Chesil Beach. Don’t miss the local seafood dining for a perfect evening together.

Things to do recommended for families

Families visiting Portland can explore the fascinating Portland Bill Lighthouse and enjoy a day at the sandy Chesil Beach. The Portland Museum offers engaging exhibits, while the nearby Jurassic Coast provides a chance to discover fossils and stunning coastal scenery, making it a perfect family adventure.

Things to do recommended for groups

Explore Portland's rich maritime history and enjoy local seafood feasts with your mates, or take part in traditional boat-building workshops, creating unforgettable memories with your group.

*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

Whether you're travelling with a group, as a family, with your pets, or seeking extended stays, be sure to refine your search with the appropriate priorities. Here are some Vrbo booking tips for you.

  • Traveling to Portland with a group: Consider the number of bedrooms required, along with amenities like a fully equipped kitchen or an outdoor area suitable for group gatherings. Luckily, you can easily filter for these and many additional features on Vrbo.
  • Traveling to Portland with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, while also looking for amenities that suit their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Portland: For many families, a trip wouldn’t feel complete without their furry companion. If that resonates with you, consider exploring Vrbo properties that welcome pets. Most 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 offering deals for stays of a month or more, you've come to the right spot. With the appropriate filter, you can effortlessly locate and save on monthly rentals. Don't forget to consider including extras like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Portland

Portland, England, is a captivating destination that offers stunning coastal scenery and rich history. Explore the rugged cliffs of the Isle of Portland, where adventure awaits with breathtaking views and outdoor activities. Enjoy the pristine beaches, perfect for relaxation or family-friendly fun. Discover the historic landmarks and enjoy the warm, friendly atmosphere that makes Portland a unique getaway in Dorset, ideal for those seeking both adventure and tranquility.

  • Weymouth: Nestled a short 8km from Portland, Weymouth is a vibrant seaside city celebrated for its expansive outdoor options and scenic charm. Visitors are drawn to its inviting beach and dramatic rock formations, perfect for family outings or a leisurely day by the sea. Local highlights include engaging water sports and the charm of a traditional recreational area, while nearby theatres offer a cultural twist to an otherwise nature-focused escape.
  • Dorchester: Situated 18km from Portland, Dorchester is a bustling city that appeals to those seeking outdoor adventures and breathtaking scenery. Its unique blend of natural beauty and recreational spaces makes it a prime destination for golf enthusiasts and explorers alike. The city’s environment is enriched by its proximity to a diverse bay and intriguing rock formations, offering a dynamic backdrop for a memorable holiday journey.
  • South Coast: Located 10km from Portland, the South Coast beckons with its promise of outdoor activities and rugged adventure. Ideal for hiking enthusiasts, its network of trail access and scenic hiking paths leads to a vast recreational area. The natural allure of national parks and striking rock formations provides a perfect setting for exploration and discovery, making it a must-visit for those who cherish unspoilt landscapes.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Looking to save on your next holiday? Try keeping your travel dates flexible since prices can fluctuate. Plus, booking a longer stay can often lead to significant savings. To discover the ideal Vrbo property that fits your budget, simply use our filters to search by price, location, and type of holiday accommodation.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board provides you with a dedicated space to start new journeys, pick up where you left off, or manage your existing bookings. Your saved or booked properties are neatly organised into Potential, Upcoming, or Current Trips. To explore Trip Boards, visit: 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:

  • Abbotsbury Swannery (10.6 mi / 17 km)
  • Warmwell Holiday Park Ski Slope (10.7 mi / 17.2 km)
  • Monkey World Ape Rescue Center (14.1 mi / 22.7 km)
  • SEA LIFE Centre Weymouth (5.6 mi / 9 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.