Upwey Holiday Rentals from €99: Search Short-Term Rentals

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Our top choices for Upwey holiday rentals

A compact kitchen with a microwave, oven, washing machine, and a sink under a window.

1. Atlantic Apartment 1

Weymouth

includes taxes & fees

17 Nov - 18 Nov

A modern kitchen with white cabinets, a wooden countertop, a built-in oven, and a window with a view of houses.

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

Weymouth Town Center

Chloe

includes taxes & fees

18 Nov - 19 Nov

A stone house with a sloped roof, surrounded by dense hedges and leafless trees, with a clear sky above.

3. Hardy View Farm House

Dorchester

Carol S.

includes taxes & fees

23 Nov - 24 Nov

A dining table set with plates of grapes, a loaf of bread, wine glasses, and a bottle of wine.

4. The Apple Loft at Jordan House

Overcombe

includes taxes & fees

19 Nov - 20 Nov

A beach with a natural rock arch formation.

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

Wool

Kristina

includes taxes & fees

29 Nov - 30 Nov

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

6. The Apple House at Moorbath Farm

Bridport

christopher b.

includes taxes & fees

3 Dec - 4 Dec

A caravan-style accommodation with a covered outdoor area, including seating and a table.

7. 1 bedroom accommodation in Ibberton, Blandford Forum

Ibberton, Blandford Forum

Paul Mitchell

includes taxes & fees

20 Nov - 21 Nov

A picnic area with a directional sign, wooden benches, and a small structure labeled 'Dorset Tea'.

8. Cosy country cottage for couples

BRIDPORT

Tracey H.

includes taxes & fees

16 Nov - 17 Nov

A garden pathway leading to a wooden gate, surrounded by lush greenery and flowering plants.

9. Battys Barn at Moorbath Farm

Bridport

Catherine L.

includes taxes & fees

16 Nov - 17 Nov

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

10. 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

16 Nov - 17 Nov

A stone building with a pitched roof, a door, and windows.

11. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

Glanvilles Wootton, near Sherborne

Caroline H.

includes taxes & fees

16 Nov - 17 Nov

A narrow water channel with stone walls and greenery on both sides.

12. The Little Cottage

Weymouth

Lea

includes taxes & fees

19 Nov - 20 Nov

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

13. 2 Bathsheba Terrace

Dorchester

Rachael

includes taxes & fees

21 Nov - 22 Nov

A wooden table with a bowl of fruit and a bottle of wine, set against a scenic backdrop of a garden and a view of the sea.

14. Sea Spray

Overcombe

includes taxes & fees

25 Nov - 26 Nov

A dining area with a wooden table set for four, a fireplace, and a staircase leading to another room.

15. 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

23 Nov - 24 Nov

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

16. Cedar Drive

Weymouth

David

includes taxes & fees

19 Nov - 20 Nov

17. Hide-a-way

Weymouth

Kim

includes taxes & fees

20 Nov - 21 Nov

A beach with waves, pebbles, and distant hills.

18. Badgers Cottage

Weymouth

Neil

includes taxes & fees

19 Nov - 20 Nov

A two-story house with a conservatory, a blue door, and a view of the sea.

19. Still Waters

Wyke Regis

Rory

includes taxes & fees

19 Nov - 20 Nov

A hot tub with a wine bottle, wicker chairs, and a wooden fence.

20. Anchor House

Westham

includes taxes & fees

26 Nov - 27 Nov

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Find holiday rentals that suit your style

Top Upwey Hotel Reviews

A rustic interior with wooden tables and chairs, a patterned carpet, and a brick wall.

The Spice Ship

Weymouth

10/10 Excellent

Ifeyinwa

A window with binoculars and a mug on the windowsill, overlooking a beach with waves and a cloudy sky.

Channel View Guest House

Weymouth Town Center

8/10 Good

Lovely location and view. Slept to the wonderful sound of lapping waves. Check-in is strictly before 7pm don’t get caught! I did and with apologies of course as it was a busy work day . The breakfast was good I took the full English breakfast and it had everything on ( depends on what you tick though so tick away) I will be back if that’s helpful to others . I did get a full smile in the morning! So yay !!

Ifeyinwa

A reception desk with a plant, a sign, and a stack of magazines.

Driftwood B&B

Westham

10/10 Excellent

Graham

A pebbled beach with a clear sky and calm sea.

Oaklands Guest House

Weymouth Town Center

10/10 Excellent

Guy

A dining area with a wooden table set for four, surrounded by chairs.

The Clarence

Weymouth Town Center

10/10 Excellent

Anonymous traveller

A beach with a statue, people, and buildings in the background.

Alexandra Hotel

Weymouth Town Center

8/10 Good

Ifeyinwa

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, apart-hotels, 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 favorite 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 depends 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 €99 per night. Entering your travel dates in the search wizard you might find 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.

Holiday Rentals in Upwey

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upwey holiday rentals

1. Atlantic Apartment 1

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

3. Hardy View Farm House

4. The Apple Loft at Jordan House

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

6. The Apple House at Moorbath Farm

7. 1 bedroom accommodation in Ibberton, Blandford Forum

8. Cosy country cottage for couples

9. Battys Barn at Moorbath Farm

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

11. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

12. The Little Cottage

13. 2 Bathsheba Terrace

14. Sea Spray

15. Norden Cottage

16. Cedar Drive

17. Hide-a-way

18. Badgers Cottage

19. Still Waters

20. Anchor House

Find holiday rentals that suit your style

Top Upwey Hotel Reviews

The Spice Ship

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?