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Upwey Holiday Rentals

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Holiday Rentals in Upwey

Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town
10.0 out of 10, Exceptional, (57)
"Quiet, peaceful location with amenities close to hand just the place for a relaxing week. Property is very well equipped and the secluded garden at the back a bonus."
United Kingdom
Chris H.
Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town
The Dorset Resort
4.0 star property
9.8 out of 10, Exceptional, (44)
"PRPOERTY VERY SPACIOUS, VERY CLEAN AND JUST A LOVELY PROPERTY TO UNWIND AND RELAX WITH FAMILY, LOVED THE SAUNA"
United Kingdom
tina
The Dorset Resort
Quiet location, short walk to beach, with views of Portland and Jurassic coast
10.0 out of 10, Exceptional, (108)
"House was exactly as described home from home, great location for exploring the area. Was our first time in Weymouth but will definitely be coming back"
United Kingdom
Anne P.
Quiet location, short walk to beach, with views of Portland and Jurassic coast
Apartment near the beach with private parking and pet friendly
9.0 out of 10, Wonderful, (30)
"Comfortable apartment with just a short walk to the beach and the centre of Weymouth."
United Kingdom
sue p.
Apartment near the beach with private parking and pet friendly
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom
9.6 out of 10, Exceptional, (45)
"A lovely relaxed stay, nice peaceful area, plenty of places to walk, highly recommend gor a bit of r&r."
United Kingdom
Spencer C.
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly
2.0 star property
The price is AU$639
includes taxes & fees
3 Nov - 4 Nov
4 Bed-2 Bath-sleeps 8-large Garden-pet Friendly
Luxury mobile home with spectacular sea views.
9.8 out of 10, Exceptional, (122)
"Very clean, great communication, amazing views."
United Kingdom
Neil
Luxury mobile home with spectacular sea views.
18 Chamberlaine Road
2.5 star property
The price is AU$809
includes taxes & fees
30 Oct - 31 Oct
18 Chamberlaine Road
The Studio - Arne
3.5 star property
The price is AU$2,806
includes taxes & fees
3 Nov - 4 Nov
The Studio - Arne
Charming Country Retreat on Old Sherbourne Road
9.0 out of 10, Wonderful, (2)
"A lovely little cabin hidden away for a break away, and a place to reset, So close to the beach and Weymouth town too was also a plus. thank you to Tracy the lovely host who made us feel so welcome."
United Kingdom
Suzie E.
Charming Country Retreat on Old Sherbourne Road
Hidden Retreat - 4 mins to beach & 3 mins to train station. Pet friendly!
8.0 out of 10, Very good, (7)
"Lovely host, well presented and loved the fact it had a bbq. Travel cot provided which helped good communication with host. "
United Kingdom
Loren T.
Hidden Retreat - 4 mins to beach & 3 mins to train station. Pet friendly!
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
9.6 out of 10, Exceptional, (21)
"Ten friends and family enjoyed a long weekend in this very pretty location. Lots to see and do near by but we also made great use of the garden and pool room."
United Kingdom
Donald M.
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
Dolmans Retreat
The price is AU$225
includes taxes & fees
27 Oct - 28 Oct
Dolmans Retreat
Leo's Place
3.0 star property
The price is AU$1,302
includes taxes & fees
31 Oct - 1 Nov
Leo's Place
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
9.6 out of 10, Exceptional, (146)
"Very pleasant stay; will pass on info to other family members for when they visit Bridport. "
United Kingdom
Peter T.
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
Luxury Pine Wood Lodge, situated in beautiful Dorset Countryside,attractions nr
9.2 out of 10, Wonderful, (92)
"A well-equipped static caravan in a lovely area. Perfect for a base, as long as you are not looking for swimming pools and night life."
United Kingdom
Richard
Luxury Pine Wood Lodge, situated in beautiful Dorset Countryside,attractions nr
Half Pint Cottage
3.0 star property
10.0 out of 10, Exceptional, (1)
"We stayed here for 3 nights, the property was spotlessly clean on arrival. Parking at the cottage was a blessing as the road outside was busy with residents cars. An ideal base to explore Dorset, and several pubs within easy walking distance. Would stay here again."
United Kingdom
nikki
The price is AU$860
includes taxes & fees
31 Oct - 1 Nov
Half Pint Cottage
Private detached cottage to rent on Chesil Beach
10.0 out of 10, Exceptional, (68)
"It was once again a perfect stay."
United Kingdom
Johnny M.
Private detached cottage to rent on Chesil Beach
Sunningdale Rise
3.0 star property
The price is AU$2,393
includes taxes & fees
31 Oct - 1 Nov
Sunningdale Rise
Ocean Swell
3.5 star property
The price is AU$1,281
includes taxes & fees
2 Nov - 3 Nov
Ocean Swell
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upwey Hotel Reviews

Find out more about Upwey

Everything you need to know about Upwey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upwey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upwey holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Upwey holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upwey. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upwey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upwey holiday rentals we have selected for you start as low as AU$225 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Upwey rentals

At Expedia, we put the best Upwey holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Upwey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upwey holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upwey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Upwey?

Yes, there are holiday rentals close to the most popular sights in Upwey, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Upwey has to offer?

Quiet location, short walk to beach, with views of Portland and Jurassic coast: This holiday home rental outside of Upwey is located on the waterfront, and has a balcony, a terrace and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of books.

What’s there to see and do in Upwey?

While exploring the area, visit family-friendly sights like SEA LIFE Centre Weymouth, or get outside and enjoy nature at Dorset Area of Outstanding Natural Beauty. In the wider area, you’ll find Durdle Door and Bowleaze Cove Beach.

What’s a holiday rental in Upwey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Upwey. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.