Upwey Vacation Rentals from $174: Search Short-Term Rentals

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Our top choices for Upwey vacation 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

$640 nightly

Oct 29 - Oct 30

Total with taxes and fees

A compact kitchen with a built-in oven, a stainless steel range hood, and a window above the sink.

2. Walkersbase - Nutallergy Friendly - Stay3 - Petsok

Bridport

$158 nightly

Nov 4 - Nov 5

Total with taxes and fees

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

3. Ash Corner Cottage

Overcombe

$909 nightly

Oct 17 - Oct 18

Total with taxes and fees

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

4. Cedar Drive

Weymouth

David

$575 nightly

Nov 6 - Nov 7

Total with taxes and fees

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

5. 2 Bathsheba Terrace

Dorchester

Rachael

$484 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

6. Sea Spray

Overcombe

$531 nightly

Oct 17 - Oct 18

Total with taxes and fees

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

7. Badgers Cottage

Weymouth

Neil

$574 nightly

Oct 17 - Oct 18

Total with taxes and fees

8. Hide-a-way

Weymouth

Kim

$457 nightly

Oct 17 - Oct 18

Total with taxes and fees

9. Sunningdale Rise

Overcombe

$1,246 nightly

Oct 17 - Oct 18

Total with taxes and fees

A grassy area with a view of a calm body of water and distant landforms.

10. Lobster Cottage

Rodwell

Sharon

$558 nightly

Oct 17 - Oct 18

Total with taxes and fees

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

11. Home Waters

Wyke Regis

$683 nightly

Oct 31 - Nov 1

Total with taxes and fees

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

$648 nightly

Oct 17 - Oct 18

Total with taxes and fees

A bedroom with a green upholstered headboard, a floral bedspread, and a painting of flowers on the wall.

13. Rodwell Holt

Weymouth

$494 nightly

Oct 23 - Oct 24

Total with taxes and fees

A room with a large window overlooking a beach, a stone wall, and a small white table.

14. Weymouth Bay Apartment C

Greenhill

STEVEN

$744 nightly

Nov 14 - Nov 15

Total with taxes and fees

A row of colorful beach huts numbered 16 to 17, with a gravel path in front.

15. Bay Cottage

Rodwell

Neil

$1,151 nightly

Oct 17 - Oct 18

Total with taxes and fees

A palm tree by a beach with a clear sky.

16. Flat 6, Thornlow Heights

Southlands

$552 nightly

Oct 17 - Oct 18

Total with taxes and fees

A harbor with boats docked, a building labeled 'The George Inn', and a cloudy sky.

17. Brewery View

Rodwell

Helen

$507 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

18. Still Waters

Wyke Regis

$883 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

19. Coastguard Lookout

Wyke Regis

$503 nightly

Oct 17 - Oct 18

Total with taxes and fees

A coastal view with boats on the water, a sandy beach, and a clear sky.

20. Beach View House

Wyke Regis

$805 nightly

Oct 22 - Oct 23

Total with taxes and fees

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Top Upwey Hotel Reviews

Durdle Door Hotel

10/10 Excellent

"Excellent location for walking to Durdle Door and beyond. Close to local pubs and restaurants. Staff are very helpful and knowledgeable. Clean and tidy bedrooms. Discounted parking across the road. Visited in late September so wasn’t too busy."

Heights Hotel

8/10 Good

"Very friendly and welcoming staff on arrival. Nice Reception area, but once you get beyond the reception the corridors and our room (203) were somewhat austere. Nice breakfast, but a wider selection of fresh fruit salad would be very welcome. The red berries were still frozen but the cooked breakfast was nice, plus a good choice of teas and coffee. Fabulous views over Chesil Beach from the restaurant, but the view from our room was compromised by the double glazing having condensation between the panes of glass (plus a net curtain for privacy). I would stay here again purely for the view and convenience of being where we needed to be (on Portland)"

The Duchess of Cornwall Inn

10/10 Excellent

"Lovely clean large room. Great tv with a superb picture. Plenty of tea / coffee and biscuits welcome tray. We were surprised how quiet our sleep was, the pub below was busy but no sound from it. The decoration of the whole venue is incredible with so much to look at. There is a lot of car spaces but the area is very busy so it’s a bit of a search to find one."

The Bull Hotel

8/10 Good

"Late online-booking led to some issues with the location end parking nearby. Which was professionally and friendly solved by the staff. The room was rather small for two. Though the bathroom was OK and clean. The hotel has an historical flair and still many original features. Breakfast was plenty een very good. We stayed for one night."

The Jubilee Hotel West- with Spa Facilities

10/10 Excellent

"The room was a good size, we had a family room for 5. The room was clean and tidy and good amenities in the room itself. The best aspect was the seaview which was fantastic helped by some good October weather. We didn't use the bar much as we were visiting relatives who live in Weymouth - but it looked good with plenty to do. The best thing about staying in the older hotels on the front is access to the beach/Weymouth centre, room size and view. Overall very happy with the hotel and the price. Would definitely stay again - thanks."

Find out more about Upwey

Everything you need to know about Upwey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upwey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Upwey vacation 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 low season months. For more hustle and bustle, you may prefer to visit Upwey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $174 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Upwey rentals

At Expedia, we put the best Upwey vacation 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 vacation.

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 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?

Classic Holiday Home for 6, relaxing family getaway near Durdle Door: Visitors like this Upwey vacation home rental. It comes with WiFi so 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 larger area, you’ll find Lodmoor Country Park and Bowleaze Cove Beach.

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.

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Check prices for these dates

Our top choices for Upwey vacation rentals

1. The Little Cottage

2. Walkersbase - Nutallergy Friendly - Stay3 - Petsok

3. Ash Corner Cottage

4. Cedar Drive

5. 2 Bathsheba Terrace

6. Sea Spray

7. Badgers Cottage

8. Hide-a-way

9. Sunningdale Rise

10. Lobster Cottage

11. Home Waters

12. Norden Cottage

13. Rodwell Holt

14. Weymouth Bay Apartment C

15. Bay Cottage

16. Flat 6, Thornlow Heights

17. Brewery View

18. Still Waters

19. Coastguard Lookout

20. Beach View House

Find vacation rentals that suit your style

Top Upwey Hotel Reviews

Durdle Door Hotel

Crown Hotel

Heights Hotel

The Duchess of Cornwall Inn

Moonfleet Manor

The Bull Hotel

The Jubilee Hotel West- with Spa Facilities

The Frampton Arms

Find out more about Upwey

Frequently asked questions

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