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, just a 1-minute walk from Weymouth Bay and 6 minutes by foot from South West Coast ...
Opens in a new windowQuiet location, short walk to beach, with views of Portland and Jurassic coast
3 Bed Holiday home close to idyllic Lulworth Cove

3 Bed Holiday home close to idyllic Lulworth Cove

West Lulworth
With a stay at this vacation home in Wareham, you'll be by the ocean, within a 10-minute drive of Durdle Door and Mupe Bay Beach.
Opens in a new window3 Bed Holiday home close to idyllic Lulworth Cove
Farm House in stunning Dorset countryside with Hardy views

Farm House in stunning Dorset countryside with Hardy views

Dorchester
The price is AU$325 per night from 16 Nov to 17 Nov
AU$325
16 Nov - 17 Nov
includes taxes & fees
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 ...
Opens in a new windowFarm House in stunning Dorset countryside with Hardy views
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4 bedroom accommodation in Weymouth

4 bedroom accommodation in Weymouth

Weymouth
With a stay at this vacation home in Weymouth, you'll be a 5-minute walk from Weymouth Harbour and 7 minutes by foot from Weymouth Marina.
Opens in a new window4 bedroom accommodation in Weymouth
Foxearth - sleeps 4 guests  in 2 bedrooms

Foxearth - sleeps 4 guests in 2 bedrooms

Blandford Forum
When you stay at this vacation home in Blandford Forum, you'll be 14 minutes by car from Dorset Area of Outstanding Natural Beauty.
Opens in a new windowFoxearth - sleeps 4 guests in 2 bedrooms
Private detached cottage to rent on Chesil Beach

Private detached cottage to rent on Chesil Beach

Abbotsbury
When you a stay at this vacation home in Weymouth, you'll be on the beach, just steps from Dorset and East Devon Coast and Chesil Beach.
Opens in a new windowPrivate detached cottage to rent on Chesil Beach
Historical, Characterful, Converted Old School House

Historical, Characterful, Converted Old School House

Lower Bockhampton
Located in Dorchester, this vacation home is in a rural location, within a 5-minute drive of Kingston Maurward Park and Gardens and Dorset Teddy Bear ...
Opens in a new windowHistorical, Characterful, Converted Old School House
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
With a stay at this vacation home in Weymouth, you'll be by the sea, within a 5-minute drive of Weymouth Beach and Weymouth Bay.
Opens in a new windowEdwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Wool
The price is AU$540 per night from 19 Nov to 20 Nov
AU$540
19 Nov - 20 Nov
includes taxes & fees
Located in Wareham, this vacation home is a 5-minute drive from Monkey World Ape Rescue Center and 6 minutes from Purbeck Shooting School.
Opens in a new windowFamily home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
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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
207 Holiday Homes
Lowest Price
AU$125
Highest Price
AU$540
Popular accommodation
Quiet location, short walk to beach, with views of Portland and Jurassic coast, 3 Bed Holiday home close to idyllic Lulworth Cove, Farm House in stunning Dorset countryside with Hardy views, 4 bedroom accommodation in Weymouth, Foxearth - sleeps 4 guests in 2 bedrooms, Private detached cottage to rent on Chesil Beach, Historical, Characterful, Converted Old School House, Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea, Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Top trending hotels in Upwey

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$191 per night from 16 Nov to 17 Nov
AU$191
16 Nov - 17 Nov
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.
Opens in a new windowBest Western Weymouth Hotel Rembrandt
Fairhaven Hotel

Fairhaven Hotel

2.5 out of 5
Fairhaven Hotel, 37 Esplanade, Weymouth, England
Fully refundableReserve now, pay when you stay
The price is AU$125 per night from 14 Nov to 15 Nov
AU$125
14 Nov - 15 Nov
includes taxes & fees
Located in Weymouth, Fairhaven Hotel is near the beach, within a 5-minute walk of Weymouth Bay and Cineworld Weymouth.
Opens in a new windowFairhaven Hotel
Durdle Door Hotel

Durdle Door Hotel

3 out of 5
West Lulworth House, Main Road, West Lulworth, Wareham, England
Fully refundableReserve now, pay when you stay
The price is AU$271 per night from 16 Nov to 17 Nov
AU$271
16 Nov - 17 Nov
includes taxes & fees
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.
Opens in a new windowDurdle Door Hotel
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George Albert Hotel & Spa

George Albert Hotel & Spa

3 out of 5
Wardon Hill Farm, Evershot, Dorchester, England
Fully refundableReserve now, pay when you stay
The price is AU$181 per night from 16 Nov to 17 Nov
AU$181
16 Nov - 17 Nov
includes taxes & fees
Located in Dorchester, George Albert Hotel & Spa is a 1-minute drive from Clay Pigeon Raceway and 6 minutes from Dorset Area of Outstanding Natural Beauty.
Opens in a new windowGeorge Albert Hotel & Spa
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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.