Photo by Sue Wormald

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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Upwey holiday rentals

Beach nearby
The Grain Store

The Grain Store

The Grain Store
3.0 star property
Weymouth
The price is ฿25,247
฿30,296 total
includes taxes & fees
26 Jan - 27 Jan
The Grain Store
Cottage | Interior
Old Higher Lighthouse Branscombe Lodge

Old Higher Lighthouse Branscombe Lodge

Old Higher Lighthouse Branscombe Lodge
3.0 star property
Portland
10.0 out of 10, Exceptional, (1 review)
"This property was absolutely amazed and having Access to one of the first lighthouses there "
United Kingdom
Trevor
The price is ฿18,595
฿22,315 total
includes taxes & fees
22 Jan - 23 Jan
Old Higher Lighthouse Branscombe Lodge
Dining
4 Bed-2 Bath-bar-pool Table-library- Xmas Venue

4 Bed-2 Bath-bar-pool Table-library- Xmas Venue

4 Bed-2 Bath-bar-pool Table-library- Xmas Venue
2.0 star property
Dorchester
The price is ฿25,891
฿36,118 total
includes taxes & fees
19 Jan - 20 Jan
4 Bed-2 Bath-bar-pool Table-library- Xmas Venue
Cottage | Exterior
Rowdens Barn

Rowdens Barn

Rowdens Barn
3.5 star property
Blandford Forum
10.0 out of 10, Exceptional, (2 reviews)
"Lovely countryside location. "
Canada
Michael
The price is ฿13,517
฿16,221 total
includes taxes & fees
18 Jan - 19 Jan
Rowdens Barn
Cottage | Private kitchen | Fridge, stovetop, cookware/dishes/utensils
Way's Forge

Way's Forge

Way's Forge
3.0 star property
Dorchester
10.0 out of 10, Exceptional, (3 reviews)
"Way's Forge is a quirky, convenient accommodation for exploring a wide variety of locations in the area and further afield. . It was a very comfortable stay and we enjoyed it very much. "
United Kingdom
Virginia
The price is ฿18,166
฿21,800 total
includes taxes & fees
26 Jan - 27 Jan
Way's Forge
Cottage | Interior
The Barn

The Barn

The Barn
3.5 star property
Beaminster
10.0 out of 10, Exceptional, (1 review)
"Absolutely lovely stay at the Barn. Such a great location: a friendly host, comfortable beds, super clean with large living areas. We will certainly be back. Great few days fossil hunting."
United Kingdom
Anonymous traveller
The price is ฿15,363
฿15,363 total
includes taxes & fees
17 Jan - 18 Jan
The Barn
Fridge, dishwasher, electric kettle, toaster
Half Pint Cottage

Half Pint Cottage

Half Pint Cottage
3.0 star property
Beaminster
10.0 out of 10, Exceptional, (1 review)
"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 ฿15,449
฿18,538 total
includes taxes & fees
17 Jan - 18 Jan
Half Pint Cottage
Property grounds
Hide-a-way

Hide-a-way

Hide-a-way
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
The price is ฿12,910
฿15,491 total
includes taxes & fees
26 Jan - 27 Jan
Hide-a-way
Cottage | Interior
Meadow View Barn

Meadow View Barn

Meadow View Barn
3.0 star property
Wareham
10.0 out of 10, Exceptional, (1 review)
"Great little place, perfect for my stay. Nice and clean, all amenities and good communication from the owner."
United Kingdom
Mitch
The price is ฿16,843
฿20,212 total
includes taxes & fees
26 Jan - 27 Jan
Meadow View Barn
Cottage | Interior
Jay Cottage

Jay Cottage

Jay Cottage
3.5 star property
Weymouth
The price is ฿13,196
฿15,835 total
includes taxes & fees
17 Jan - 18 Jan
Jay Cottage
Cottage | Interior
Old Harbour View

Old Harbour View

Old Harbour View
3.5 star property
Weymouth
9.6 out of 10, Exceptional, (4 reviews)
"Apartment was excellent with stunning views of the harbour and local fishing community."
United Kingdom
Caroline
The price is ฿23,566
฿28,279 total
includes taxes & fees
17 Jan - 18 Jan
Old Harbour View
Marina
Day Cottage

Day Cottage

Day Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"The cottage was absolutely excellent , clean, had everything you need,cosy, couldn’t ask for more ,also not far from the beach "
United Kingdom
Cindy
The price is ฿14,090
฿16,908 total
includes taxes & fees
24 Jan - 25 Jan
Day Cottage
Cottage | Marina
2 Driftwood

2 Driftwood

2 Driftwood
3.5 star property
Bridport
10.0 out of 10, Exceptional, (2 reviews)
"2 Driftwood was a perfect place to stay at the perfect location of West Bay. The flat is very new, immaculate and well equipped with all you need for a holiday stay. Only one issue we had was finding the meter cupboard where the key safe was located. This is outside of the rear entrance of the building at ground level. One of the residents advised us of the key safe location and said many other guests had struggled with this. Everything else was perfect and Iwould love to live there."
United Kingdom
Debbie
The price is ฿15,770
฿18,924 total
includes taxes & fees
10 Feb - 11 Feb
2 Driftwood
Cottage | Interior
Badbury Lodge

Badbury Lodge

Badbury Lodge
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
The price is ฿19,039
฿22,846 total
includes taxes & fees
18 Jan - 19 Jan
Badbury Lodge
Cottage | Interior
Little Tern

Little Tern

Little Tern
3.5 star property
Weymouth
The price is ฿22,350
฿26,820 total
includes taxes & fees
18 Jan - 19 Jan
Little Tern
Cottage | Beach | Beach nearby
Barton Cottage

Barton Cottage

Barton Cottage
3.5 star property
Bridport
The price is ฿13,424
฿16,109 total
includes taxes & fees
18 Jan - 19 Jan
Barton Cottage
Beach nearby
The Loft @ No36

The Loft @ No36

The Loft @ No36
3.0 star property
Weymouth
The price is ฿16,307
฿19,568 total
includes taxes & fees
17 Jan - 18 Jan
The Loft @ No36
Cottage | Interior
Firkin Cottage

Firkin Cottage

Firkin Cottage
3.5 star property
Weymouth
8.0 out of 10, Very good, (1 review)
"The stay in general was fantastic With a great location The Firkin cottage was a good size, but the bathrooms really need updating "
United Kingdom
M A
The price is ฿18,859
฿22,631 total
includes taxes & fees
18 Jan - 19 Jan
Firkin Cottage
Cottage | Interior
The Shambles

The Shambles

The Shambles
3.5 star property
Portland
The price is ฿22,314
฿26,777 total
includes taxes & fees
18 Jan - 19 Jan
The Shambles
2 bedrooms, individually decorated, individually furnished, free WiFi
26 High West

26 High West

26 High West
3.0 star property
Weymouth
8.0 out of 10, Very good, (1 review)
"The cottage has everything that is needed amenitieswise a short walk from the harbour and town and a little longer to the beach. The only reason i gave 4 for cleaness was the property needed a bit of a touch up paintwise but nothing drastic an was probably due to a long summer season and clients not givin property due care."
United Kingdom
Robert
The price is ฿14,288
฿17,146 total
includes taxes & fees
18 Jan - 19 Jan
26 High West
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

The Smugglers Inn

The Smugglers Inn

10/10 Excellent
"Really warm welcome at the hotel, taken to our room which was very clean cosy and snuggly. Amenities in the room excellent and we were catered for well, including sufficient space for the dogs. Ate two nights in the bar/restaurant, staff very good, food lovely, excellent selection for gluten free which was amazing to experience. A lovely restful couple of days and made To feel exceptionally welcome "
Tim 2-night trip
Posted 5 days ago
The Smugglers Inn

Find out more about Upwey

Search for holiday rentals in Upwey on Expedia! You can easily find your home rentals, villas, holiday apartments in Upwey using one of the methods below:

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Look no further and take a look at our great range of rental properties in Upwey!

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’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 Bowleaze Cove Beach and Osmington Bay 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.