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

Upwey Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Upwey vacation rentals

The Little Cottage

The Little Cottage
3.0 star property
Weymouth
The price is CA $914
CA $1,097 total
includes taxes & fees
Jul 27 - Jul 28
The Little Cottage

Hardy View Farm House

Hardy View Farm House
Dorchester
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely Fabulous Stay at this Farmhouse. Wonderful hosts in Luba and Chris who were so informative and helpful.Lovely property inside and out. So relaxing and peaceful. Missing the wonderful breakfasts already. 10 out of 10 !!"
Australia
Carol S.
The price is CA $302
CA $345 total
includes taxes & fees
Aug 9 - Aug 10
Hardy View Farm House

Duck Cottage, Sutton Poyntz

Duck Cottage, Sutton Poyntz
Weymouth
The price is CA $2,495
CA $2,495 total
includes taxes & fees
Aug 17 - Aug 18
Duck Cottage, Sutton Poyntz

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
10.0 out of 10, Exceptional, (4 reviews)
"Responsive owner and lovely property"
United Kingdom
Benjamin
The price is CA $321
CA $691 total
includes taxes & fees
Aug 4 - Aug 5
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Ideal Spring Breaks for Couples

Ideal Spring Breaks for Couples
Morcombelake
9.8 out of 10, Exceptional, (6 reviews)
"Great place to stay, "
United Kingdom
Gary C.
The price is CA $225
CA $370 total
includes taxes & fees
Jul 27 - Jul 28
Ideal Spring Breaks for Couples

Spring Cottage Escape for Couples

Spring Cottage Escape for Couples
BRIDPORT
9.4 out of 10, Exceptional, (6 reviews)
"We had a great stay ...house was lovely, well equipped & communication was very good with owner."
United Kingdom
Tracey H.
The price is CA $230
CA $373 total
includes taxes & fees
Jul 23 - Jul 24
Spring Cottage Escape for Couples

The Halt Maiden Newton, Dorset

The Halt Maiden Newton, Dorset
Dorchester
The price is CA $648
CA $648 total
includes taxes & fees
Aug 10 - Aug 11
The Halt Maiden Newton, Dorset

Sea View Coastal Cottage Sleeps 6 | Jurassic Coast, 6-Min Walk to Beach, Dogs

Sea View Coastal Cottage Sleeps 6 | Jurassic Coast, 6-Min Walk to Beach, Dogs
Fortuneswell
10.0 out of 10, Exceptional, (3 reviews)
"We had a great stay in Portland. The house had everything we needed, as a base to explore the local area. "
United Kingdom
Ruby C.
Sea View Coastal Cottage Sleeps 6 | Jurassic Coast, 6-Min Walk to Beach, Dogs

Battys Barn at Moorbath Farm

Battys Barn at Moorbath Farm
Bridport
10.0 out of 10, Exceptional, (6 reviews)
"Host was very helpful with good communication. The property was very well presented and very clean. It was a really nice stay."
United Kingdom
James A.
The price is CA $569
CA $710 total
includes taxes & fees
Aug 21 - Aug 22
Battys Barn at Moorbath Farm

1 bedroom accommodation in Ibberton, Blandford Forum

1 bedroom accommodation in Ibberton, Blandford Forum
Ibberton, Blandford Forum
10.0 out of 10, Exceptional, (11 reviews)
"Great location & lovely place to stay, had everything you need for a weekend break or longer…"
United Kingdom
Dominic
The price is CA $402
CA $402 total
includes taxes & fees
Aug 20 - Aug 21
1 bedroom accommodation in Ibberton, Blandford Forum

Sea Spray

Sea Spray
3.0 star property
Overcombe
The price is CA $759
CA $910 total
includes taxes & fees
Aug 9 - Aug 10
Sea Spray

Spacious, entire 3 bedroom house in Wool (The Purbecks)

Spacious, entire 3 bedroom house in Wool (The Purbecks)
Wool
The price is CA $566
CA $778 total
includes taxes & fees
Aug 9 - Aug 10
Spacious, entire 3 bedroom house in Wool (The Purbecks)

The Apple House at Moorbath Farm

The Apple House at Moorbath Farm
Bridport
10.0 out of 10, Exceptional, (5 reviews)
"Really nice property ,all nicely finished to a high standard.liked the oak used. We had a nice few days-if you want somewhere peaceful and quiet this is ideal. "
United Kingdom
christopher b.
The price is CA $360
CA $501 total
includes taxes & fees
Jul 26 - Jul 27
The Apple House at Moorbath Farm

Keepers Cottage, Winterborne Stickland

Keepers Cottage, Winterborne Stickland
Blandford Forum
9.4 out of 10, Exceptional, (3 reviews)
"Quiet but well located for many Dorset attractions"
United Kingdom
Peter M.
The price is CA $793
CA $793 total
includes taxes & fees
Aug 5 - Aug 6
Keepers Cottage, Winterborne Stickland

South Lodge, Hazelbury Bryan

South Lodge, Hazelbury Bryan
Sturminster Newton
The price is CA $812
CA $812 total
includes taxes & fees
Aug 9 - Aug 10
South Lodge, Hazelbury Bryan

The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

The Old Police House, sleeps 10, 1850,s cottage, Family Stay!
Winterborne Whitechurch
10.0 out of 10, Exceptional, (1 review)
"Great place!"
United States
Cord
The price is CA $755
CA $862 total
includes taxes & fees
Jul 27 - Jul 28
The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

Half Pint Cottage, Beaminster.

Half Pint Cottage, Beaminster.
Beaminster
The price is CA $897
CA $897 total
includes taxes & fees
Aug 8 - Aug 9
Half Pint Cottage, Beaminster.

Oke Apple Cottage, Okeford Fitzpaine

Oke Apple Cottage, Okeford Fitzpaine
Blandford Forum
The price is CA $1,177
CA $1,177 total
includes taxes & fees
Aug 14 - Aug 15
Oke Apple Cottage, Okeford Fitzpaine

Coastguard Lookout

Coastguard Lookout
2.0 star property
Weymouth
The price is CA $719
CA $862 total
includes taxes & fees
Aug 10 - Aug 11
Coastguard Lookout

2 Bathsheba Terrace

2 Bathsheba Terrace
3.0 star property
Dorchester
10.0 out of 10, Exceptional, (2 reviews)
"Everything was there that we needed. It was clean, well laid out and comfortable. "
Canada
Rachael
The price is CA $706
CA $847 total
includes taxes & fees
Aug 3 - Aug 4
2 Bathsheba Terrace
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Upwey Hotel Reviews

Find out more about Upwey

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Upwey. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Upwey?

Yes, we offer vacation rentals near well known points of interest in Upwey, or you can go with a secluded option if you'd like a relaxing place to stay.

What are some of the best vacation home rentals that Upwey has to offer?

Quiet location, short walk to beach, with views of Portland and Jurassic coast: You might want to consider this vacation rental near Upwey, which is located on the waterfront and has a balcony, a terrace, and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of books.

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 larger area, you’ll find Durdle Door and Lodmoor Country Park.

What’s a vacation rental in Upwey like?

Vacation rentals are private properties you can book for a long or short time in Upwey. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for families.