A lush garden with a pond, ferns, and flowering plants.

Upwey Holiday Rentals

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Upwey holiday rentals

Exterior

The Little Cottage

The Little Cottage
3.0 star property
Weymouth
The price is S$1,011
includes taxes & fees
31 Jul - 1 Aug
The Little Cottage
Property grounds

Beautiful Pad Near World Heritage Jurassic Coast

Beautiful Pad Near World Heritage Jurassic Coast
3.0 star property
Bridport
The price is S$350
includes taxes & fees
18 Jul - 19 Jul
Beautiful Pad Near World Heritage Jurassic Coast
Property grounds

Manhattan Beach

Manhattan Beach
3.0 star property
Portland
The price is S$1,609
includes taxes & fees
20 Jul - 21 Jul
Manhattan Beach
Dining

Sunningdale Rise

Sunningdale Rise
3.0 star property
Overcombe
The price is S$2,920
includes taxes & fees
20 Jul - 21 Jul
Sunningdale Rise
Terrace/patio

Ash Corner Cottage

Ash Corner Cottage
2.0 star property
Overcombe
The price is S$1,596
includes taxes & fees
20 Jul - 21 Jul
Ash Corner Cottage
Beach

Braiders Rest

Braiders Rest
3.0 star property
Bridport
The price is S$892
includes taxes & fees
22 Jul - 23 Jul
Braiders Rest
Dining

Amy Cottage

Amy Cottage
3.0 star property
Wareham
The price is S$1,301
includes taxes & fees
20 Jul - 21 Jul
Amy Cottage
Fridge, dishwasher, electric kettle, toaster

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 S$766
includes taxes & fees
28 Jul - 29 Jul
Half Pint Cottage
Interior

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 S$1,513
includes taxes & fees
30 Jul - 31 Jul
Old Higher Lighthouse Branscombe Lodge
Front of property

Beach View House

Beach View House
3.5 star property
Weymouth
The price is S$1,276
includes taxes & fees
22 Jul - 23 Jul
Beach View House
Interior

Still Waters

Still Waters
2.0 star property
Weymouth
The price is S$1,396
includes taxes & fees
31 Jul - 1 Aug
Still Waters
Beach

The View

The View
2.0 star property
Portland
The price is S$2,300
includes taxes & fees
31 Jul - 1 Aug
The View
Interior

The Studio - Arne

The Studio - Arne
3.5 star property
Wareham
The price is S$6,383
includes taxes & fees
20 Jul - 21 Jul
The Studio - Arne
Beach nearby

Flat 6, Thornlow Heights

Flat 6, Thornlow Heights
3.0 star property
Weymouth
The price is S$873
includes taxes & fees
16 Aug - 17 Aug
Flat 6, Thornlow Heights
Interior

The Cow Shed

The Cow Shed
3.0 star property
Dorchester
The Cow Shed
Private kitchen

Coastguard Lookout

Coastguard Lookout
2.0 star property
Weymouth
The price is S$797
includes taxes & fees
28 Jul - 29 Jul
Coastguard Lookout
2 bedrooms, individually decorated, individually furnished, free WiFi

Sea Spray

Sea Spray
3.0 star property
Overcombe
The price is S$842
includes taxes & fees
28 Jul - 29 Jul
Sea Spray
Beach

74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is S$819
includes taxes & fees
31 Jul - 1 Aug
74 Reap Lane
Beach

Keepers Cottage

Keepers Cottage
3.5 star property
Blandford Forum
The price is S$709
includes taxes & fees
16 Aug - 17 Aug
Keepers Cottage
Marina

Brewery View

Brewery View
2.0 star property
Weymouth
The price is S$802
includes taxes & fees
31 Jul - 1 Aug
Brewery View
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

Aaran Guesthouse

Aaran Guesthouse

8/10 Good
"Great location at tip of Esplanade. Somewhat older and worn guesthouse, could do with a refresh such as carpets. No fans in room (A/C not expected) but fridge was an excellent surprise. Very friendly."
Gordon 1-night trip
Posted 7 hours ago
Aaran Guesthouse

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 Durdle Door and Lodmoor Country Park.

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.