Book Holiday Homes in Upwey

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Featured Holiday Homes in Upwey

Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast

Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast

Wyke Regis
When you stay at this vacation home in Weymouth, you'll be on the waterfront, within a 10-minute drive of Weymouth Harbour and Weymouth Beach.
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Gorgeous Georgian Home

Gorgeous Georgian Home

Weymouth
With a stay at this vacation home in Weymouth, you'll be within a 10-minute drive of Weymouth Beach and Weymouth Harbour.
Gorgeous Georgian Home
Luxury Detached House and Grounds, also benefits from full disabled facilities.

Luxury Detached House and Grounds, also benefits from full disabled facilities.

Whitcombe
With a stay at this vacation home in Dorchester, you'll be near the beach, within a 15-minute drive of Weymouth Beach and Max Gate.
Luxury Detached House and Grounds, also benefits from full disabled facilities.
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Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)

Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)

West Milton
Located in Bridport, this vacation home is in a rural location, within a 15-minute drive of Mangerton Mill and Mapperton Gardens.
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Stunning 1-bedroom coach house with free parking

Stunning 1-bedroom coach house with free parking

Weymouth
With a stay at this vacation home in Weymouth, you'll be within a 10-minute drive of Weymouth Beach and Weymouth Harbour.
Stunning 1-bedroom coach house with free parking
Stone's Throw, open plan modern house, a short walk from Chesil Beach

Stone's Throw, open plan modern house, a short walk from Chesil Beach

Portland
When you stay at this vacation home in Portland, you'll be by the ocean, within a 10-minute drive of Weymouth Harbour and Weymouth Beach.
Stone's Throw, open plan modern house, a short walk from Chesil Beach
3 Bed Holiday home close to idyllic Lulworth Cove

3 Bed Holiday home close to idyllic Lulworth Cove

West Lulworth
When you stay at this vacation home in Wareham, you'll be by the ocean, a 2-minute drive from Lulworth Cove and 5 minutes from Durdle Door.
3 Bed Holiday home close to idyllic Lulworth Cove
Seafeathers - Luxury Holiday Home with Sea Views

Seafeathers - Luxury Holiday Home with Sea Views

Weymouth
With a stay at this vacation home in Weymouth (Overcombe), you'll be a 4-minute drive from Weymouth Beach and 6 minutes from Weymouth Harbour.
Seafeathers - Luxury Holiday Home with Sea Views
 Beautiful, family friendly Cottage with sea views of Chesil Beach

Beautiful, family friendly Cottage with sea views of Chesil Beach

Fortuneswell
When you stay at this vacation home in Portland, you'll be by the sea, within a 10-minute drive of Weymouth Harbour and Weymouth Beach.
Beautiful, family friendly Cottage with sea views of Chesil Beach
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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
186 Holiday Homes
Lowest Price
AU$116
Highest Price
AU$260
Popular accommodation
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast , Gorgeous Georgian Home, Luxury Detached House and Grounds, also benefits from full disabled facilities., Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly), Stunning 1-bedroom coach house with free parking, Stone's Throw, open plan modern house, a short walk from Chesil Beach, 3 Bed Holiday home close to idyllic Lulworth Cove, Seafeathers - Luxury Holiday Home with Sea Views, Beautiful, family friendly Cottage with sea views of Chesil Beach

Top trending hotels in Upwey

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$116 per night from 2 Jun to 3 Jun
AU$116
per night
2 Jun - 3 Jun
With a stay at Fairhaven Hotel in Weymouth, you'll be near the beach, a 3-minute walk from Weymouth Harbour and 6 minutes by foot from Weymouth Beach.
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$205 per night from 9 Jun to 10 Jun
AU$205
per night
9 Jun - 10 Jun
When you stay at Best Western Weymouth Hotel Rembrandt in Weymouth, you'll be by the sea, within a 5-minute drive of Weymouth Beach and Weymouth Harbour.
Best Western Weymouth Hotel Rembrandt
The Jubilee Hotel - with Spa, Restaurant and Entertainment

The Jubilee Hotel - with Spa, Restaurant and Entertainment

3 out of 5
143-146 The Esplanade, Weymouth, England
Fully refundableReserve now, pay when you stay
The price is AU$260 per night from 4 Jun to 5 Jun
AU$260
per night
4 Jun - 5 Jun
With a stay at The Jubilee Hotel - with Spa, Restaurant and Entertainment, you'll be centrally located in Weymouth, within a 5-minute drive of Weymouth Beach ...
The Jubilee Hotel - with Spa, Restaurant and Entertainment
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Heights Hotel

Heights Hotel

3 out of 5
Yeates Road, Portland, England
The price is AU$249 per night from 2 Jun to 3 Jun
AU$249
per night
2 Jun - 3 Jun
Located in Portland, Heights Hotel is a 2-minute drive from Verne High Angle Battery and 6 minutes from Portland Bill Lighthouse.
Heights Hotel
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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.