Photo by Sue Wormald

Upwey holiday rentals

We found 851 holiday rentals — enter your dates for availability
Discover a selection of 9 cottages and other holiday rentals in Upwey that are perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll find the amenities that you need and want, which might include a fireplace and a washer and dryer. You'll be able to choose a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

  • Peace of mind

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  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Choose a holiday rental for your Upwey getaway

Learn about the unique charm of Upwey with a stay in a holiday home rental. This city has something for everyone. Whether you're planning a family holiday, romantic stay or trip with friends, holiday rentals offer features like full kitchens and laundry facilities for a more convenient stay.

Sightseeing in and around Upwey

Are you hoping to discover attractions to visit during your stay? Venture out of your holiday home and check out everything that makes Upwey a fun spot to go on holiday. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Abbotsbury Swannery (5.8 mi / 9.4 km)
  • Warmwell Holiday Park Ski Slope (5.9 mi / 9.4 km)
  • Monkey World Ape Rescue Center (11.3 mi / 18.1 km)
  • SEA LIFE Centre Weymouth (2.7 mi / 4.4 km)
  • Bridport and West Dorset Golf Club (12.5 mi / 20.1 km)
  • Pirate Adventure Mini Golf (2.7 mi / 4.4 km)

Exploring the natural landscape of Upwey

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Upwey is a great place to get outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Lodmoor Country Park (2.5 mi / 4 km)
  • Bowleaze Cove Beach (2.8 mi / 4.4 km)
  • Weymouth Beach (3.7 mi / 5.9 km)
  • Weymouth Harbour (3.8 mi / 6.1 km)
  • Weymouth Bay (5 mi / 8 km)
  • Chesil Beach (5.8 mi / 9.4 km)

Travelling to and around Upwey

Fly into Bournemouth (BOH-Bournemouth Intl.), the closest airport, located 29 mi (46.6 km) from the city centre.

Frequently asked questions

What is the best area to stay in Upwey when booking a holiday rental?
When considering a holiday rental in Upwey, a charming village located in Dorset, you'll find that staying close to the village centre offers a lovely experience. This area features a variety of properties, providing a good selection for visitors seeking a quaint getaway. One of the highlights of Upwey is its picturesque surroundings, particularly the nearby Upwey Wishing Well, which is a delightful spot featuring beautiful gardens and a café, superb for a relaxing afternoon.Additionally, being just a short distance from the bustling town of Weymouth, guests can easily access stunning beaches and the famous Weymouth Harbour. The proximity to these attractions enhances the appeal of Upwey, making it an ideal base for exploring the stunning Jurassic Coast and enjoying the local charm while still being close to vibrant seaside activities.
When is the best time to visit Upwey for a holiday rental?
The peak travel season in Upwey is during the summer months, particularly from June to August, when visitors flock to enjoy the picturesque Dorset coastline and the charming local attractions. July stands out as the most popular month, offering a vibrant setting filled with activities and events that cater to families and outdoor enthusiasts alike.During this period, temperatures are usually mild and pleasant, ranging from around 15 to 25 degrees Celsius, making it ideal for outdoor adventures such as hiking along the scenic South West Coast Path or exploring the nearby Jurassic Coast, a UNESCO World Heritage Site. The long days provide ample opportunity for sightseeing and enjoying the local culture, whether you're indulging in the charming shops or sampling delicious fare at quaint eateries.If you're looking for more budget-friendly options, consider visiting Upwey in November. This month allows for a more tranquil experience, where you can appreciate the beauty of the autumn landscape and take leisurely strolls without the bustling crowds. The lower demand for holiday rentals during this time can also mean better rates, allowing you to enjoy the same stunning scenery and local charm at a fraction of the price.Ultimately, the best time to visit Upwey hinges on your preferences—whether you thrive in the lively summer atmosphere with plenty of activities or you prefer the serene beauty of the quieter months.
What are the top attractions in Upwey?
In Upwey, visitors can enjoy a variety of attractions that showcase the charm of this picturesque village. One top highlight is the beautiful Upwey Wishing Well, a historic site with lovely gardens and a tea room, superb for a relaxing afternoon. The nearby Upwey and Broadwey village is known for its quaint character and offers scenic walks along the River Wey, ideal for those who appreciate nature and tranquility.For those interested in history, the area is in proximity to the larger town of Weymouth, where attractions such as the historic Nothe Fort and the stunning Weymouth Beach can be easily accessed. The delightful countryside surrounding Upwey also features numerous walking trails, providing opportunities for outdoor exploration.
Are all fees included in the Upwey holiday homes prices shown on Stayz?
Stayz 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.
Are there any Upwey holiday homes with parking?
Stayz offers a wide selection of holiday homes in Upwey with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Upwey holiday homes?
You can find great discounts on holiday homes in Upwey on Stayz, 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.
Can I change or cancel my Upwey holiday home booking on Stayz?
To find Upwey holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Upwey?
A long-stay holiday home in Upwey is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Upwey holiday home?
Book your Upwey holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Upwey?
Prices for holiday homes in Upwey 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Upwey to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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