Holiday Rentals Upwey from £390: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Upwey holiday rentals

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

1. The Little Cottage

Weymouth

Lea

includes taxes & fees

11 Nov - 12 Nov

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

2. Hardy View Farm House

Dorchester

Carol S.

includes taxes & fees

12 Nov - 13 Nov

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

includes taxes & fees

8 Nov - 9 Nov

A coastal area with a beach, a pier, and a hillside with vegetation.

4. Jurassic Coast Durdle Door, Lulworth Cove cabin

West Lulworth

includes taxes & fees

9 Nov - 10 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

8 Nov - 9 Nov

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

6. 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

8 Nov - 9 Nov

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

9 Nov - 10 Nov

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

8. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

Glanvilles Wootton, near Sherborne

Caroline H.

includes taxes & fees

16 Nov - 17 Nov

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

8 Nov - 9 Nov

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

10. The Apple House at Moorbath Farm

Bridport

christopher b.

includes taxes & fees

8 Nov - 9 Nov

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

11. Cedar Drive

Weymouth

David

includes taxes & fees

11 Nov - 12 Nov

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

12. Cosy country cottage for couples

BRIDPORT

Tracey H.

includes taxes & fees

9 Nov - 10 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

11 Nov - 12 Nov

14. Hide-a-way

Weymouth

Kim

includes taxes & fees

11 Nov - 12 Nov

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

15. 2 Bathsheba Terrace

Dorchester

Rachael

includes taxes & fees

21 Nov - 22 Nov

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

16. Badgers Cottage

Weymouth

Neil

includes taxes & fees

11 Nov - 12 Nov

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

17. 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

11 Nov - 12 Nov

A palm tree by a beach with a clear sky.

18. Flat 6, Thornlow Heights

Southlands

includes taxes & fees

11 Nov - 12 Nov

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

19. Coastguard Lookout

Wyke Regis

includes taxes & fees

22 Nov - 23 Nov

A wooden deck with a pergola, a table with chairs, and a brick pathway.

20. Home Waters

Wyke Regis

includes taxes & fees

11 Nov - 12 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

Lisa

A restaurant with a large copper dome, wooden tables, and potted plants.

The Duchess of Cornwall Inn

Dorchester

10/10 Excellent

Anna

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

Carol

A thatched-roof building with wicker furniture and hanging flower baskets.

Yalbury Cottage

Dorchester

10/10 Excellent

What an awesome find ! As good as anywhere I have ever stayed beautiful building fabulously comfortable and so relaxing. So much effort must go into delivering such exceptional customer service. Rooms are large well stocked ( brownie tasters left with coffee were unreal - thanks apprentice Ben!) warm and comfortable. Food here really deserves to be enjoyed at length as I struggle to think when I have tasted food prepared so well with an imaginative twist on the menu - first class! Breakfast I...

Phill

A table with various bottles and glasses of drinks, including a raspberry liqueur, tonic water, pink grapefruit gin, and fever-tree tonic water, set outdoors with a green umbrella and a stone wall in the background.

The Frampton Arms

Dorchester

10/10 Excellent

KEITH

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

Anonymous traveller

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

Vivian

A kitchen with a green countertop, a coffee machine, and jars of spices.

Driftwood B&B

Westham

10/10 Excellent

Chris

A building with a black iron balcony and hanging flower baskets.

The Clarence

Weymouth Town Center

10/10 Excellent

JUNE

A room with a purple sofa, a grey sofa, and a white table with a vase of flowers.

Sleeping Bear Hotel Dorchester

Dorchester

10/10 Excellent

Anonymous traveller

A table set with a vase of flowers, salt and pepper shakers, a teapot, and cutlery, overlooking a coastal view with buildings and a red buoy.

The Anchorage

Weymouth Town Center

10/10 Excellent

Maggie

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

10/10 Excellent

Megan

A bedroom with a bed, a nightstand, a lamp, a wardrobe, and a view of the outdoors through large windows.

Lulworth Cove Inn

Wareham

10/10 Excellent

James

A bedroom with a bed, two bedside tables, a chandelier, and a geometric-patterned wall.

Ashmira Guest House

Greenhill

10/10 Excellent

Pauline

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 £390 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.

Search Holiday Rentals in Upwey

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Upwey holiday rentals

1. The Little Cottage

2. Hardy View Farm House

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

4. Jurassic Coast Durdle Door, Lulworth Cove cabin

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

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

7. 1 bedroom accommodation in Ibberton, Blandford Forum

8. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

9. Battys Barn at Moorbath Farm

10. The Apple House at Moorbath Farm

11. Cedar Drive

12. Cosy country cottage for couples

13. Sea Spray

14. Hide-a-way

15. 2 Bathsheba Terrace

16. Badgers Cottage

17. Norden Cottage

18. Flat 6, Thornlow Heights

19. Coastguard Lookout

20. Home Waters

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?