Upwey Holiday Rentals from €152: Search Short-Term Rentals

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Our top choices for Upwey holiday rentals

A stone house with a paved patio, a small garden, and a view of the sea.

1. Ash Corner Cottage

Overcombe

includes taxes & fees

7 Oct - 8 Oct

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

2. Hardy View Farm House

Dorchester

Carol S.

includes taxes & fees

29 Oct - 30 Oct

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

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

Weymouth Town Center

Chloe

A beach with people, a large striped tower, and buildings in the background.

4. The Sailors Studio|Sleeps2|Weymouth Beach|

Weymouth Town Center

includes taxes & fees

7 Oct - 8 Oct

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

11 Oct - 12 Oct

A marina with boats docked, a statue in the foreground, and buildings in the background.

6. The Lighthouse Suite|Sleeps4|Weymouth Beach|

Weymouth Town Center

"Property very difficult to find as out of date pictures & false impression of outside. Property inside was fairly clean. But access stairs & Outlook really let it down as not clean. Apartmentment was well equipped & comfortable. Sadly shower was not working nor was the fan in the bathroom. It is however in a very noisy area late at night & early in the morning, so personally would not stay here with children. However it is very close to all amenities."

Lynn

includes taxes & fees

4 Oct - 5 Oct

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

7. 1 bedroom accommodation in Ibberton, Blandford Forum

Ibberton, Blandford Forum

Paul Mitchell

includes taxes & fees

2 Oct - 3 Oct

A picnic table in a grassy area with a wooden fence and trees in the background.

8. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

Glanvilles Wootton, near Sherborne

Caroline H.

includes taxes & fees

12 Oct - 13 Oct

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

9. Battys Barn at Moorbath Farm

Bridport

James A.

includes taxes & fees

6 Oct - 7 Oct

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

10. Cosy country cottage for couples

BRIDPORT

Tracey H.

includes taxes & fees

5 Oct - 6 Oct

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

11. Sea Spray

Overcombe

includes taxes & fees

29 Oct - 30 Oct

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

12. 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

26 Oct - 27 Oct

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

13. The Apple House at Moorbath Farm

Bridport

christopher b.

includes taxes & fees

4 Oct - 5 Oct

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

14. Badgers Cottage

Weymouth

Neil

includes taxes & fees

14 Oct - 15 Oct

A coastal area with a beach, boats, and a clear sky.

15. Marina Vista

Southlands

"Great, well appointed apartment which is very central. Can be quite noisy at night especially having to have the windows open when it’s hot. Seemed to be a popular location for late night drinkers to have heart to hearts in the wee hours. Can’t fault the apartment, it had everything you could need. Minutes away from the town and beach. On the rainy days we had there were even board games for kids which my son loved. Thanks for a great stay. "

M

includes taxes & fees

7 Oct - 8 Oct

16. Hide-a-way

Weymouth

Kim

includes taxes & fees

4 Oct - 5 Oct

A marina with multiple sailboats docked along a waterfront promenade.

17. Harbour Reach 7

Weymouth

Austin

includes taxes & fees

13 Oct - 14 Oct

18. Anchor Cottage

Weymouth Town Center

Carolyn

includes taxes & fees

4 Oct - 5 Oct

A wicker table with a bottle of wine, a bowl of fruit, two glasses, and a magazine.

19. Two @ No36

Weymouth Town Center

includes taxes & fees

7 Oct - 8 Oct

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

20. 2 Bathsheba Terrace

Dorchester

Rachael

includes taxes & fees

13 Oct - 14 Oct

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Top Upwey Hotel Reviews

The Jubilee Hotel East- with Spa Facilities

8/10 Good

"We had to move rooms as the first one was too small. The staff were very helpful and moved us into a lovely spacious room. There was plenty to eat at breakfast with a good choice of hot or cold buffet food."

Belhuish Farmhouse

10/10 Excellent

"This property is unique and rare - owned by an innkeeper who welcomes you to his table with warm hospitality and decades of history to share. Mr. Miller is a wealth of information and retired thatcher. This is not a place for you if you need a well-appointed hotel to feel good about leaving your home. This is a historic property with purbeck flag stones and Welsh slate on the kitchen floor. The stove is as wide as your arms. There are wild pheasants in the fields and silent nights nestled in a hidden valley a bit off the main road. This a place where ruins of the past sit on the land beside a welcoming farmhouse. Great for introverts, writers, couples, families, and solo travelers. Backpackers will love it."

Lulworth Cove Inn

10/10 Excellent

"We loved our stay at the Lulworth Cove. The parking wasn’t free and it was a bit difficult but doable. The room was very clean and the bed was comfortable. The restaurant was very good and the area was beautiful and very walkable. There are several trails along the cliffs and the coast and we felt very safe walking around. Having to lug our suitcases up 2 flights of stairs was difficult but because we prefer to stay in older, more historic buildings, not having a lift was expected. I would definitely stay here again."

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 €152 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upwey holiday rentals

1. Ash Corner Cottage

2. Hardy View Farm House

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

4. The Sailors Studio|Sleeps2|Weymouth Beach|

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

6. The Lighthouse Suite|Sleeps4|Weymouth Beach|

7. 1 bedroom accommodation in Ibberton, Blandford Forum

8. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

9. Battys Barn at Moorbath Farm

10. Cosy country cottage for couples

11. Sea Spray

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

13. The Apple House at Moorbath Farm

14. Badgers Cottage

15. Marina Vista

16. Hide-a-way

17. Harbour Reach 7

18. Anchor Cottage

19. Two @ No36

20. 2 Bathsheba Terrace

Find holiday rentals that suit your style

Top Upwey Hotel Reviews

The Jubilee Hotel East- with Spa Facilities

The Frampton Arms

Kingston Country Courtyard

Belhuish Farmhouse

Driftwood B&B

Lulworth Cove Inn

Fairhaven Hotel

Sleeping Bear Hotel Dorchester

The Bull Hotel

Find out more about Upwey

Frequently asked questions

Go further with the Expedia app

Holiday Rentals in Upwey

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upwey holiday rentals

1. Ash Corner Cottage

2. Hardy View Farm House

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

4. The Sailors Studio|Sleeps2|Weymouth Beach|

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

6. The Lighthouse Suite|Sleeps4|Weymouth Beach|

7. 1 bedroom accommodation in Ibberton, Blandford Forum

8. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

9. Battys Barn at Moorbath Farm

10. Cosy country cottage for couples

11. Sea Spray

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

13. The Apple House at Moorbath Farm

14. Badgers Cottage

15. Marina Vista

16. Hide-a-way

17. Harbour Reach 7

18. Anchor Cottage

19. Two @ No36

20. 2 Bathsheba Terrace

Find holiday rentals that suit your style

Top Upwey Hotel Reviews

The Jubilee Hotel East- with Spa Facilities

Find out more about Upwey

Frequently asked questions

Go further with the Expedia app