Book Holiday Homes in Upwey

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Featured Holiday Homes in Upwey

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
With a stay at this vacation home in Weymouth, you'll be on the waterfront, within a 10-minute drive of Weymouth Beach and Weymouth Bay.
Quiet location, short walk to beach, with views of Portland and Jurassic coast
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
With a stay at this vacation home in Weymouth, you'll be on the waterfront, within a 10-minute drive of Weymouth Beach and Weymouth Bay.
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset

Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset

Sturminster Newton
Located in Sturminster Newton, this vacation home is on a river, within a 10-minute drive of Dorset Area of Outstanding Natural Beauty and Badger Watch ...
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset
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Beautiful large Georgian house with a big garden. Perfect for a family or two!

Beautiful large Georgian house with a big garden. Perfect for a family or two!

Wareham
When you stay at this vacation home in Wareham, you'll be by the sea, within a 15-minute drive of Poole Harbour and Corfe Castle.
Beautiful large Georgian house with a big garden. Perfect for a family or two!
The Victorian Barn self catering holidays with pool & hot tubs

The Victorian Barn self catering holidays with pool & hot tubs

4 out of 5
Dairy House Farm Woolland, Blandford Forum, England
With a stay at The Victorian Barn self catering holidays with pool & hot tubs in Blandford Forum, you'll be 12.4 mi (20 km) from Cerne Abbas Giant and 19.9 mi ...
The Victorian Barn self catering holidays with pool & hot tubs
 Beautiful, family friendly Cottage with sea views of Chesil Beach

Beautiful, family friendly Cottage with sea views of Chesil Beach

Fortuneswell
With a stay at this vacation home in Portland, you'll be by the sea, within a 10-minute drive of Weymouth Beach and Dorset and East Devon Coast.
Beautiful, family friendly Cottage with sea views of Chesil Beach
Farm House in stunning Dorset countryside with Hardy views

Farm House in stunning Dorset countryside with Hardy views

Dorchester
With a stay at this vacation home in Dorchester, you'll be within a 15-minute drive of Dorset Area of Outstanding Natural Beauty and The Keep Military ...
Farm House in stunning Dorset countryside with Hardy views
  Barn conversion, quiet location and  heated swimming  pool ( from mid May)

Barn conversion, quiet location and heated swimming pool ( from mid May)

Dorchester
With a stay at this vacation home in Dorchester, you'll be by the sea, within a 15-minute drive of Weymouth Beach and Maiden Castle.
Barn conversion, quiet location and heated swimming pool ( from mid May)
4 bedroom accommodation in Weymouth

4 bedroom accommodation in Weymouth

Weymouth
With a stay at this vacation home in Weymouth, you'll be by the ocean, within a 5-minute drive of Weymouth Beach and Jubilee Clock Tower of Weymouth.
4 bedroom accommodation in Weymouth
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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.

Upwey Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Upwey vacation homes are the perfect way for you to wing it.

Holiday houses in Upwey let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Upwey in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Upwey adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Upwey with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Upwey vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Upwey Holiday Homes essential information

Accommodation
260 Holiday Homes
Lowest Price
AU$150
Highest Price
AU$257
Popular accommodation
Quiet location, short walk to beach, with views of Portland and Jurassic coast, Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach, Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset, Beautiful large Georgian house with a big garden. Perfect for a family or two!, The Victorian Barn self catering holidays with pool & hot tubs, Beautiful, family friendly Cottage with sea views of Chesil Beach , Farm House in stunning Dorset countryside with Hardy views, Barn conversion, quiet location and heated swimming pool ( from mid May) , 4 bedroom accommodation in Weymouth

Top trending hotels in Upwey

Fairhaven Hotel

Fairhaven Hotel

2.5 out of 5
Fairhaven Hotel, 37 Esplanade, Weymouth, England
The price is AU$150 per night from 10 Aug to 11 Aug
AU$150
10 Aug - 11 Aug
includes taxes & fees
When you stay at Fairhaven Hotel in Weymouth, you'll be near the beach, within a 10-minute walk of Weymouth Beach and Weymouth Bay.
Fairhaven Hotel
Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

3 out of 5
12-18 Dorchester Road, Weymouth, England
Fully refundableReserve now, pay when you stay
The price is AU$257 per night from 17 Aug to 18 Aug
AU$257
17 Aug - 18 Aug
includes taxes & fees
With a stay at Best Western Weymouth Hotel Rembrandt in Weymouth, you'll be by the sea, within a 5-minute drive of Weymouth Beach and Greenhill Beach.
Best Western Weymouth Hotel Rembrandt
The Jubilee Hotel East- with Spa Facilities

The Jubilee Hotel East- with Spa Facilities

3 out of 5
143-146 The Esplanade, Weymouth, England
With a stay at The Jubilee Hotel East- with Spa Facilities, you'll be centrally located in Weymouth, within a 5-minute drive of Weymouth Beach and Weymouth ...
The Jubilee Hotel East- with Spa Facilities
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Durdle Door Hotel

Durdle Door Hotel

3 out of 5
West Lulworth House, Main Road, West Lulworth, Wareham, England
Located in Wareham, Durdle Door Hotel is in a rural location, within a 15-minute walk of Weymouth Bay and Dorset and East Devon Coast.
Durdle Door Hotel
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See all available properties in Upwey
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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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^Subject to availability and chosen travel dates.