Portland vacation rentals

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Select from 17 homes, 81 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.

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Find out more about Portland

Why visit Portland

  • Stunning Beaches: Portland, England boasts beautiful beaches perfect for relaxation and outdoor fun.
  • Historic Castles: Explore the rich history of the area by visiting its impressive castles.
  • Picturesque Harbor: Enjoy the scenic views and vibrant atmosphere at the charming harbor.
  • Cozy Accommodations: Choose from a variety of vacation rentals, including charming cottages and spacious homes.
  • Friendly Neighborhoods: Experience the warmth of the local community in inviting, family-friendly areas.

Popular types of accommodation in Portland

When planning your getaway to Portland, you'll find a variety of vacation rentals to suit your needs. From charming cottages and spacious private homes to cozy studio apartments, there's something for everyone. Enjoy a convenient stay in the heart of the city or escape to a peaceful Oregon retreat. Discover the perfect Portland vacation rental that offers transparency, savings, and reassurance for an unforgettable experience.

  • Cottages: The top choice for vacation rentals in Portland, these charming properties offer a cozy and scenic retreat.
  • Houses: Ideal for groups or families, these homes provide a spacious and comfortable setting for your stay.
  • Apartments: A convenient option for solo travelers or couples, offering modern amenities in the heart of the city.
  • Cabins: Perfect for those seeking a rustic experience, these rentals immerse you in nature.
  • Caravan Parks: A fun and budget-friendly choice, these parks offer a unique outdoor camping experience.**

Top attractions near Portland

Portland, England, is a fantastic destination for outdoor enthusiasts and adventure seekers, featuring stunning beaches, historic castles, and a picturesque harbor. Travelers can immerse themselves in local culture while enjoying the scenic beauty and outdoor activities that the area offers. Don't miss out on exploring downtown Portland, where you can find a variety of attractions and experiences to enhance your visit.

  • Chesil Beach: A stunning pebble beach stretching along the coastline, Chesil Beach offers a unique beach vibe perfect for leisurely walks and picnics. The natural beauty and serene atmosphere make it a great spot to relax and enjoy the sound of the waves.
  • Weymouth Harbour: This picturesque harbor is known for its vibrant marine life and charming scenery. Enjoy a stroll along the waterfront, explore quaint shops, and indulge in fresh seafood while soaking in the coastal ambiance.
  • Weymouth Bay: A beautiful bay that combines outdoor activities with breathtaking scenery. Perfect for sailing, swimming, or simply enjoying the sun, Weymouth Bay is an ideal destination for beach lovers and adventure seekers alike.

Things to do recommended for couples

For a romantic getaway in Portland, indulge in water sports at the Weymouth and Portland National Sailing Academy. Enjoy a fun round at Pirate Adventure Mini Golf nearby, then savor a delightful meal at Mangerton Mill, where the ambiance is perfect for couples.

Things to do recommended for families

Families can unwind at Lodmoor Country Park, just 6 miles from Portland, or enjoy the sun at Greenhill Beach, located 5 miles away. For sports enthusiasts, The Avenue Stadium, 11 miles from Portland, offers an exciting atmosphere perfect for all ages.

Things to do recommended for groups

Groups visiting Portland can enjoy a performance at the Weymouth Pavilion, catch a movie at Cineworld Weymouth, or tee off at the Bridport and West Dorset Golf Club for a fun day outdoors. Each venue offers unique experiences perfect for creating lasting memories together.

*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 traveling with a group, with family, bringing your pets, or planning an extended stay, be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips for you.

  • Traveling to Portland with a group: Think about how many bedrooms you require and any additional features like a complete kitchen or outdoor area for group gatherings. Luckily, you can easily filter for these options and so much more on Vrbo.
  • Traveling to Portland with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private 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, a family vacation isn't truly enjoyable without their furry companion by their side. If this resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly accommodations come equipped with feeding bowls and beds, ensuring that your entire family feels comfortable and at home.
  • Planning for a long term stay visiting Portland: If you're seeking vacation rentals that offer special rates 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 rental options. Also, think about including amenities like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay near Portland

Portland, England, offers a charming blend of outdoor adventures and rich history, making it an ideal vacation spot. Explore picturesque landscapes, cozy cottages, and friendly neighborhoods that invite relaxation and family-friendly fun. Nearby cities and attractions provide a perfect backdrop for exciting experiences, whether you seek luxury or adventure. Discover the unique vibes that make Portland a delightful destination for travelers looking to unwind and explore.

  • Weymouth: Situated a mere 5 miles from Portland, Weymouth is a vibrant coastal city renowned for its stunning outdoor experiences and scenic beauty. Visitors can enjoy a plethora of activities, including theater performances and recreational areas perfect for family outings. The city's highlights include its beautiful beaches, ideal for sunbathing or swimming, and impressive rock formations that offer opportunities for exploration. Weymouth's charming seaside atmosphere makes it a must-visit destination for adventure seekers and nature lovers alike.
  • South Coast: Located about 6 miles from Portland, the South Coast is famous for its breathtaking scenery and outdoor adventures. This area boasts numerous hiking trails that cater to both beginners and seasoned hikers, providing access to stunning views of the coastline and surrounding natural beauty. Additionally, the South Coast features shopping mall centers, allowing travelers to indulge in some retail therapy after a day of exploration. Local highlights include picturesque national parks and serene beaches, making it an ideal spot for those looking to immerse themselves in nature.
  • Dorchester: Approximately 11 miles from Portland, Dorchester is a historic city that offers visitors a unique blend of outdoor activities and scenic landscapes. With its recreational areas and campgrounds, Dorchester is perfect for those who enjoy camping and outdoor adventures. The nearby national park is a highlight, providing a chance to connect with nature, while the beautiful beaches and rugged rocks are perfect for a day of relaxation or exploration. Dorchester is a delightful destination for travelers seeking adventure and stunning scenery.

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. Peak season runs from July to September, while off-peak times, like January to February and November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January44.6°F (7.0°C)Light RainMostly CloudyLowAverage
February44.4°F (6.9°C)Light RainMostly CloudyLowSlightly Low
March46.0°F (7.8°C)Light RainMostly CloudyAverageSlightly Low
April49.1°F (9.5°C)Light RainMostly SunnyAverageAverage
May53.8°F (12.1°C)Light RainMostly SunnyAverageAverage
June58.8°F (14.9°C)Light RainMostly SunnyAverageAverage
July62.2°F (16.8°C)Light RainMostly SunnyHighSlightly High
August62.4°F (16.9°C)Light RainMostly SunnyHighSlightly High
September60.3°F (15.7°C)Light RainMostly SunnyHighAverage
October56.5°F (13.6°C)Light RainMostly CloudyAverageAverage
November50.9°F (10.5°C)Light RainMostly CloudyLowSlightly Low
December47.3°F (8.5°C)Light RainMostly CloudyAverageSlightly High

Booking with Vrbo is a breeze

Are you hoping to save money on your next getaway? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to take advantage of substantial savings. To discover a Vrbo property that matches your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform where you can easily plan new trips, resume previous ones, and manage your travel arrangements. You can view your saved or booked properties organized into sections for Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

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:

  • Abbotsbury Swannery (10.6 mi / 17 km)
  • Monkey World Ape Rescue Center (14.1 mi / 22.7 km)
  • SEA LIFE Centre Weymouth (5.6 mi / 9 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)
  • 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)
  • Bowleaze Cove Beach (6.3 mi / 10.2 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, England, United Kingdom when booking a vacation rental?
When looking for a great area to stay in Portland, England, a fantastic choice is the vicinity of the Chesil Beach. This stunning natural wonder offers breathtaking views and a unique landscape, making it a superb backdrop for your vacation. The area is known for its charming coastal atmosphere and easy access to outdoor activities such as walking, cycling, and birdwatching.

Another appealing part of Portland is the area around the Portland Bill Lighthouse, which not only provides picturesque scenery but also serves as a popular spot for photography and leisurely strolls along the coastline. This part of Portland boasts a variety of vacation rentals, suiting different preferences and budgets. The combination of scenic views and local attractions makes this area an ideal base for exploring the rich maritime history and natural beauty that Portland has to offer.
How much does it cost to rent a vacation home in Portland?
Prices for vacation rentals in Portland vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Portland to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Portland vacation house rentals?
You can find great discounts on house rentals in Portland on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Portland?
For renting a beach house in Portland, England, travelers should focus on the scenic coastal areas of Dorset, particularly around the picturesque area of Chesil Beach. This stretch features stunning views and easy access to the pebbled beach, where visitors can enjoy walks along the shore and watch the tide come in. Many beach house rentals in this vicinity come with amenities such as outdoor seating areas, barbecues, and fully equipped kitchens, superb for family gatherings or romantic getaways.

Additionally, the nearby town of Weymouth offers a vibrant seaside atmosphere, with properties that often include features like private balconies and sea views. Here, visitors can explore the historic harbor, dine at local seafood restaurants, and indulge in water sports. Rentals in Weymouth frequently provide convenient access to the sandy beaches, as well as amenities like parking and Wi-Fi, enhancing the overall experience for travelers.

Just a short drive away, the stunning Jurassic Coast World Heritage Site awaits, allowing for exploration of beautiful cliffs and fossil hunting. Many accommodations in this area are designed for comfort and relaxation, often featuring gardens or patios where guests can unwind after a day of beach activities or hiking along the coast.
What is the most popular type of vacation rental accomodation in Portland?
In Portland, cottages are the most popular type of vacation rental, with around 72 available throughout the area. These charming properties are typically found in picturesque settings, providing a cozy atmosphere that appeals to travelers seeking a quaint experience. Most cottages come equipped with fully functional kitchens, comfortable living spaces, and often feature outdoor seating areas for enjoying the fresh coastal air.

Additionally, there are about 14 vacation houses available, which offer more space and amenities, making them suitable for families or larger groups. These homes usually include multiple bedrooms, private gardens, and sometimes even BBQ facilities for those looking to enjoy outdoor dining.
Are there any family house rentals in Portland?
In Portland, England, numerous family-friendly rentals are available, with about 49 options to choose from. The area features a variety of properties that cater to families, ensuring an enjoyable stay. Many of these homes come equipped with spacious living areas, fully stocked kitchens for preparing family meals, and outdoor spaces where children can play and explore.

Travelers will find accommodations in neighborhoods close to the stunning Jurassic Coast, a UNESCO World Heritage Site known for its breathtaking scenery and fossil-rich cliffs. Additionally, properties near the vibrant town center offer easy access to local attractions, shops, and eateries. Many rentals also feature modern conveniences such as Wi-Fi and laundry facilities, enhancing the overall comfort of your stay.
Can I rent a vacation home with a pool or hot tub in Portland?
In Portland, England, there are several vacation homes available for rent that feature pools and hot tubs. Travelers can find properties in various neighborhoods, each offering a unique charm. Many of these rentals come equipped with private pools, hot tubs, and well-designed outdoor spaces, superb for relaxing after a day of exploring the picturesque surroundings. Inside, guests can expect amenities such as fully equipped kitchens, spacious living areas, and comfortable bedrooms, ensuring a pleasant and convenient stay.
Can I find long-stay vacation rentals in Portland?
A long-stay vacation rental in Portland is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Portland?
In Portland, England, travelers can find a variety of pet-friendly house rentals, with approximately 42 options available to accommodate guests traveling with pets. Many of these rentals are situated in charming coastal neighborhoods, providing easy access to local attractions and outdoor spaces.

Visitors can expect amenities such as fully equipped kitchens, spacious living areas, and private gardens or patios, allowing for a comfortable stay. Some properties also feature additional conveniences like laundry facilities and designated parking spaces, making them ideal for families or groups.

The area around Portland offers beautiful coastal walks, stunning views, and access to nearby parks, which are superb for pet owners looking to explore the outdoors with their furry companions. Notable nearby points of interest include the scenic Chesil Beach and the historic Portland Bill Lighthouse, both of which provide lovely environments for outdoor activities and leisurely strolls.
Are there any remote work vacation rentals in Portland?
In Portland, England, there are numerous remote work vacation rentals available—around 94 options throughout the area. Travelers can expect a variety of properties equipped with essential amenities to support their work-from-home needs. Many rentals offer complimentary Wi-Fi, often available in both public areas and within the rooms, ensuring connectivity for remote tasks.

The town itself features charming accommodations that blend comfort with convenience, allowing guests to enjoy a productive stay while exploring local attractions. With its scenic coastal views and proximity to historical sites, Portland provides a stimulating environment for both work and leisure. Visitors can take breaks by enjoying the picturesque landscapes or visiting nearby points of interest, such as the Portland Bill Lighthouse and the beautiful Chesil Beach. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Portland vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Portland with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Portland?
In Portland, popular vacation rental amenities cater to various traveler needs, with many properties featuring fully equipped kitchens, allowing guests to prepare their meals during their stay. The proximity to the beach enhances the appeal, as numerous rentals are located just a short walk from the coast, making it easy to enjoy seaside activities. Additionally, many rentals in the area are pet-friendly, permitting guests to bring their furry companions along, which is a significant draw for animal lovers. Furthermore, service animals are welcome, ensuring accessibility for all. Free WiFi is commonly available, allowing guests to stay connected during their visit.
When is the best time to visit Portland for a vacation rental?
The most popular time to visit Portland, England, is in August, when summer is in full swing and the weather is typically at its warmest. This vibrant month attracts a bustling crowd, as visitors flock to enjoy the coastal scenery, partake in outdoor activities, and explore the charming local market. With temperatures usually ranging from the low 60s to mid-70s Fahrenheit, it's an inviting time for walks along the beach or leisurely strolls through historic streets.

The peak travel season runs from June to August, appealing to those who thrive on the energy of fellow travelers and the abundance of summer events. Whether you're interested in sailing, cycling, or simply soaking up the sun, Portland offers a variety of activities to keep you engaged. The long daylight hours mean you can make the most of your time, enjoying everything from coastal walks to vibrant community festivals.

If you're looking for a more budget-friendly option, consider visiting in December. While this month may have cooler temperatures, it presents a unique opportunity to experience the cozy charm of Portland during the quieter winter season. You can enjoy peaceful walks along the coast and take in the breathtaking views without the summer crowds.

Ultimately, the best time to book a vacation rental in Portland depends on your preference for lively summer adventures or a tranquil winter retreat.
How early should I book a Portland vacation rental?
Book your Portland vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Portland, England, United Kingdom?
In Portland, England, visitors can explore several captivating attractions. The Isle of Portland itself is known for its stunning coastal scenery, with the iconic Portland Bill Lighthouse offering breathtaking views of the Jurassic Coast. Nearby, the historic Portland Castle, built during the reign of Henry VIII, provides insights into the area's rich maritime past and has beautiful gardens to stroll through.

In the village of Fortuneswell, travelers can find a variety of charming local shops and cafes, making it a lovely spot to enjoy a leisurely afternoon. The Portland Museum, located in Easton, showcases the island's history and culture, while the surrounding area features beautiful walking trails with panoramic views of the sea and surrounding landscape.

For those interested in outdoor activities, the Chesil Beach, which connects Portland to the mainland, is great for walking, cycling, and birdwatching. The nearby Tout Quarry offers unique sculptures and stunning views, making it a popular destination for art and nature enthusiasts alike.
Can I change or cancel my Portland home rental booking on Vrbo?
To find Portland vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Portland vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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