Photo by Sue Wormald

Upwey Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Upwey holiday rentals

Apartment near the beach with private parking and pet friendly

Apartment near the beach with private parking and pet friendly
Weymouth
9.2 out of 10, Wonderful, (31)
"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 Dorset Resort

The Dorset Resort
4.0 star property
Wareham
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

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Weymouth
10.0 out of 10, Exceptional, (51)
"Outstanding house in ideal location. I could have sat in the garden all week!"
United Kingdom
Robert G.
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

Beachside, stunning apartment with sea and harbour views

Beachside, stunning apartment with sea and harbour views
West Bay, Bridport
9.6 out of 10, Exceptional, (74)
"Great property with all the facilities you need (even sky sports), great location and superb communication with the host. Would definitely stay again.."
United Kingdom
Marie E.
Beachside, stunning apartment with sea and harbour views

The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom
Maiden Newton
9.6 out of 10, Exceptional, (46)
"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

Luxury barn conversion sleeping 16 with hot tub and ensuite bedrooms

Luxury barn conversion sleeping 16 with hot tub and ensuite bedrooms
Woolland Blandford Forum
9.4 out of 10, Exceptional, (10)
"The property was perfect for what we needed - so much useable space that even with a group of 15 of us we never felt on top of each other. The facilities on site were brilliant for families - something for everyone and the swimming pool was a definite win! The location is remote and incredibly beautiful. An absolute perfect place for a getaway "
United Kingdom
Heather M.
Luxury barn conversion sleeping 16 with hot tub and ensuite bedrooms

Quiet location, short walk to beach, with views of Portland and Jurassic coast

Quiet location, short walk to beach, with views of Portland and Jurassic coast
Wyke Regis
10.0 out of 10, Exceptional, (109)
"Lovely Cottage for a Great vacation. "
Germany
Victoria Sylvia H.
Quiet location, short walk to beach, with views of Portland and Jurassic coast

Dolmans Retreat

Dolmans Retreat
Lytchett Matravers
The price is AU$222
includes taxes & fees
17 Dec - 18 Dec
Dolmans Retreat

18 Chamberlaine Road

18 Chamberlaine Road
2.5 star property
Weymouth
The price is AU$804
includes taxes & fees
28 Dec - 29 Dec
18 Chamberlaine Road

Characterful 18th century cottage in Bridport close to the Jurassic Coast.

Characterful 18th century cottage in Bridport close to the Jurassic Coast.
Bridport
10.0 out of 10, Exceptional, (71)
"Lovely cottage, perfect location Will definitely try to go again at some point "
United Kingdom
Peter L.
Characterful 18th century cottage in Bridport close to the Jurassic Coast.

The Secret: Stylish and Spacious En Suite Bathroom

The Secret: Stylish and Spacious En Suite Bathroom
Blandford Forum
9.0 out of 10, Wonderful, (2)
"Unique centrally located "
United Kingdom
Jennifer
The price is AU$183
includes taxes & fees
7 Jan - 8 Jan 2026
The Secret: Stylish and Spacious En Suite Bathroom

Leo's Place

Leo's Place
3.0 star property
Weymouth
Leo's Place

The Studio - Arne

The Studio - Arne
3.5 star property
Wareham
The price is AU$2,710
includes taxes & fees
16 Jan - 17 Jan 2026
The Studio - Arne

Luxury mobile home with spectacular sea views.

Luxury mobile home with spectacular sea views.
Weymouth
9.8 out of 10, Exceptional, (124)
"Very clean, great communication, amazing views."
United Kingdom
Neil
Luxury mobile home with spectacular sea views.

Half Pint Cottage

Half Pint Cottage
3.0 star property
Beaminster
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$855
includes taxes & fees
20 Dec - 21 Dec
Half Pint Cottage

Private detached cottage to rent on Chesil Beach

Private detached cottage to rent on Chesil Beach
Abbotsbury
10.0 out of 10, Exceptional, (68)
"Greenbanks is outstanding and most definitely 5 starLocation is superb , the house was impeccable , we thoroughly enjoyed our stay and will hopefully visit again "
United Kingdom
Anonymous traveller
Private detached cottage to rent on Chesil Beach

Upwey - Wessex Quarters

Upwey - Wessex Quarters
Weymouth
8.0 out of 10, Very good, (1)
"Excellent location. Well priced convenient parking near property "
United Kingdom
rachel g.
Upwey - Wessex Quarters

Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
Weymouth
8.8 out of 10, Excellent, (45)
"A lovely stay in Weymouth. Minutes to the beach and the train station. Harbour within 15 minutes. Downstairs space amazing . "
United Kingdom
Gemma K.
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea

Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake

Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake
2.0 star property
Dorchester
Tadnoll Escape- Shepards Hut- Sleeps 2- Bbq- Lake

Delightful thatched cottage in beautiful sleepy Dorset village and countryside

Delightful thatched cottage in beautiful sleepy Dorset village and countryside
West Knighton, nr Dorchester, Dorset
9.8 out of 10, Exceptional, (53)
"Cracking property very well equipped, excellent all round cottage, lovely setting."
United Kingdom
Robert F.
Delightful thatched cottage in beautiful sleepy Dorset village and countryside
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.
Save an average of 15% on thousands of hotels when you're signed in

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$183 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?

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach: This holiday home rental outside of Upwey is located on the waterfront, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Kick off your shoes and enjoy yourself 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 Abbotsbury Swannery, or get outside and enjoy nature at Dorset Area of Outstanding Natural Beauty. In the wider area, you’ll find Lodmoor Country Park 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.