Upwey Holiday Rentals from AU$161: Search Short-Term Rentals

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Our top choices for Upwey holiday rentals

A cozy living room with a green sofa, a dining table set with plates and cups, and a variety of wall art.

1. Cosy Peacehaven. Free on site Parking! Pet friendly!

Weymouth Town Center

Chloe

includes taxes & fees

29 Nov - 30 Nov

A bathroom with a window, a sink, and two potted plants.

2. Hardy View Farm House

Dorchester

Carol S.

includes taxes & fees

25 Nov - 26 Nov

A cozy living room with a grey sofa, a green throw blanket, and a dining area with wicker chairs.

3. 2 Bathsheba Terrace

Dorchester

Rachael

includes taxes & fees

26 Nov - 27 Nov

A beach with a natural rock arch formation.

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

Wool

Kristina

includes taxes & fees

15 Nov - 16 Nov

A stone house with a thatched-roof extension, a stone well, and a grassy yard.

5. The Apple House at Moorbath Farm

Bridport

christopher b.

includes taxes & fees

3 Dec - 4 Dec

A small wooden structure with a door and steps leading up to it, surrounded by greenery and a picnic table with cushions.

6. 1 bedroom accommodation in Ibberton, Blandford Forum

Ibberton, Blandford Forum

Paul Mitchell

includes taxes & fees

3 Dec - 4 Dec

A brick house with a sloped roof, a patio with a table and chairs, and a garden with various plants.

7. Battys Barn at Moorbath Farm

Bridport

Catherine L.

includes taxes & fees

30 Nov - 1 Dec

A two-story house with a sloped roof, a front porch with chairs, and a small garden area.

8. Cosy country cottage for couples

BRIDPORT

Tracey H.

includes taxes & fees

17 Nov - 18 Nov

A cozy room with exposed brick walls, wooden beams, and a mix of leather and fabric seating.

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

Winterborne Whitechurch

"Excellent cottage! Super quirky and perfect for a large group. My husband’s family all met at the Langham vineyard (jut 8 minute’s drive up the road from the accommodation) to celebrate his 50th ; adults, kids, dog…we had a wonderful time and carried on the celebrations with an evening of chat in the comfortable lounge and some food in the spacious dining area before heading to bed (all 10 of us). Martin was a wonderful host, very quick responses and super accommodating. The whole area is...

Stacia B.

includes taxes & fees

15 Nov - 16 Nov

A cozy living room with a fireplace, wooden furniture, and a comfortable sofa.

10. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

Glanvilles Wootton, near Sherborne

Caroline H.

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a white exterior, a stone wall on the right, and a small garden with potted plants and flowers.

11. The Little Cottage

Weymouth

Lea

includes taxes & fees

17 Nov - 18 Nov

A cozy room with a stone wall, a fireplace, a sofa, and a window.

12. Norden Cottage

Weymouth

"The cottage itself is lovely, and has a lot of potential. It’s a large cottage which accomodates 5. Lighting wasn’t working in all rooms which was a nuisance and the facilities in the kitchen were dirty and not maintained well. Oven and stove worked, coffee machine filthy. Given that you would hire a cottage to do self catering, it wasn’t one of the better cottages we have stayed in. We found it a cold welcoming, no welcome note, only a small box of biscuits on entry. Cottage was really...

Hilary

includes taxes & fees

27 Nov - 28 Nov

A bedroom with a bed, a wooden chair, a desk with a mirror, and a window with curtains.

13. Sea Spray

Overcombe

includes taxes & fees

27 Nov - 28 Nov

A residential property with a patio, a sliding glass door, and a brick exterior.

14. Cedar Drive

Weymouth

David

includes taxes & fees

26 Nov - 27 Nov

15. Hide-a-way

Weymouth

Kim

includes taxes & fees

18 Nov - 19 Nov

A room with a large window overlooking a body of water, a small table with candles, and a mirror on the wall.

16. Still Waters

Wyke Regis

Rory

includes taxes & fees

19 Nov - 20 Nov

17. Anchor House

Westham

includes taxes & fees

26 Nov - 27 Nov

A modern kitchen with a dining area, featuring a large window, a microwave, and a sink.

18. Coastguard Lookout

Wyke Regis

includes taxes & fees

22 Nov - 23 Nov

A traditional stone building with a thatched roof, a small window, and a sign prohibiting parking on the grass.

19. Badgers Cottage

Weymouth

Neil

includes taxes & fees

27 Nov - 28 Nov

A wide, pebbled beach with a clear sky and calm sea.

20. Chandlers Nook

Portland

includes taxes & fees

19 Nov - 20 Nov

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Find holiday rentals that suit your style

Top Upwey Hotel Reviews

A modern living room with a fireplace, a sofa, a dining table, and a view of the garden.

Birch House B&B

Radipole

10/10 Excellent

Craig

A white door with the number 8, a black mailbox, and a stone wall with purple flowers.

The Heritage Bed & Breakfast

Weymouth

10/10 Excellent

Kathleen

A traditional pub with a clock, wooden beams, and outdoor seating.

The Smugglers Inn

Weymouth

10/10 Excellent

Leonore

A modern dining area with a round table set for six, large windows, and a view of the garden.

Bay Tree House

Dorchester

10/10 Excellent

Nice and clean - a good stay. The hosts were really great when I arrived quite late at night due to a missed train, and were really helpful in making sure I could get right into my room easily. I really appreciated their helpfulness and easy communication. There are a number of pets about the house including dogs, who make a bit of noise in the evening and early morning, but not too bad. I would be quite happy to stay here again.

Olivia

A corner building with a bay window, a black wrought iron balcony, and a brick facade.

The Clarence

Weymouth Town Center

10/10 Excellent

Katherine

A room with a large window overlooking a beach, a table with a vase of flowers, and a chair with a floral pattern.

Beach View Guesthouse

Weymouth Town Center

10/10 Excellent

Peter

A dining area with a wooden table and chairs, a potted plant, and a large window with natural light.

Coach House Inn

Dorchester

8/10 Good

Alan

Find out more about Upwey

Everything you need to know about Upwey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upwey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upwey holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Upwey holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Upwey. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upwey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upwey holiday rentals we have selected for you start as low as AU$161 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Upwey rentals

At Expedia, we put the best Upwey holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Upwey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upwey holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upwey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 are some of the best holiday rentals that Upwey has to offer?

Classic Holiday Home for 6, relaxing family getaway near Durdle Door: This holiday home rental outside of Upwey comes with WiFi so that you can feel at home during your trip. Kitchen amenities include a fridge, a stovetop and a microwave.

What’s there to see and do in Upwey?

While exploring the area, visit family-friendly sights like Abbotsbury Swannery, or get outside and enjoy nature at Dorset National Landscape. In the wider area, you’ll find Lodmoor Country Park and Bowleaze Cove Beach.

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.

Upwey Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upwey holiday rentals

1. Cosy Peacehaven. Free on site Parking! Pet friendly!

2. Hardy View Farm House

3. 2 Bathsheba Terrace

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

5. The Apple House at Moorbath Farm

6. 1 bedroom accommodation in Ibberton, Blandford Forum

7. Battys Barn at Moorbath Farm

8. Cosy country cottage for couples

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

10. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

11. The Little Cottage

12. Norden Cottage

13. Sea Spray

14. Cedar Drive

15. Hide-a-way

16. Still Waters

17. Anchor House

18. Coastguard Lookout

19. Badgers Cottage

20. Chandlers Nook

Find holiday rentals that suit your style

Top Upwey Hotel Reviews

Birch House B&B

10/10 Excellent

Find out more about Upwey

Upwey holiday rentals: An excellent choice for every season

How to find incredible deals on Upwey rentals

Frequently Asked Questions

Can I find a holiday rental in Upwey?

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

What’s there to see and do in Upwey?

What’s a holiday rental in Upwey like?