A lush garden with a pond, ferns, and flowering plants.

Upwey Vacation Rentals

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    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Upwey vacation rentals

Exterior

1. The Little Cottage

The Little Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Clean cottage, great location, comfortable beds."
Australia
Lea
$653 nightly
The price is $784
Aug 14 - Aug 15
Total with taxes and fees
The Little Cottage
2 bedrooms, WiFi (free), individually decorated, individually furnished

2. Sea Spray

Sea Spray
3.0 star property
Overcombe
$542 nightly
The price is $650
Aug 8 - Aug 9
Total with taxes and fees
Sea Spray
Outdoor dining

3. 39 Greenlands, Littlesea Holiday Park

39 Greenlands, Littlesea Holiday Park
3.0 star property
Weymouth
$383 nightly
The price is $460
Aug 16 - Aug 17
Total with taxes and fees
39 Greenlands, Littlesea Holiday Park
Interior

4. 2 Bathsheba Terrace

2 Bathsheba Terrace
3.0 star property
Dorchester
10.0 out of 10, Exceptional, (2 reviews)
"Everything was there that we needed. It was clean, well laid out and comfortable. "
Canada
Rachael
$494 nightly
The price is $593
Aug 23 - Aug 24
Total with taxes and fees
2 Bathsheba Terrace
Property grounds

5. Hide-a-way

Hide-a-way
2.5 star property
Weymouth
10.0 out of 10, Exceptional, (2 reviews)
"It was in a peaceful location, although a bit far for walking into town. But the facilities were spot on, though there is no oven to cook proper meals. For someone who needs a quiet, chilled out, restful timeout, it is the perfect place to stay."
United Kingdom
Kim
$466 nightly
The price is $560
Aug 16 - Aug 17
Total with taxes and fees
Hide-a-way
Exterior

6. Bracken Cottage

Bracken Cottage
3.0 star property
Weymouth
8.0 out of 10, Very Good, (1 review)
"Had a great 6 night stay here. Check in was very easy, key safe on the wall outside. As soon as we got inside the cottage, which had a lovely warm welcoming cosy feel to it. We loved all the little extra decorations scattered around. Well stocked with plates, glasses cutlery etc.. Even some extras that we didn't expect like the smoothie blender and spice rack. Only downside was all the towels were bundled in a heap on the bathroom floor. Not sure what had happened here, whether the cleaners had...
United Kingdom
michael
$516 nightly
The price is $619
Aug 14 - Aug 15
Total with taxes and fees
Bracken Cottage
Beach nearby

7. Betty's Buoy

Betty's Buoy
2.0 star property
Weymouth
$484 nightly
The price is $580
Aug 10 - Aug 11
Total with taxes and fees
Betty's Buoy
Cottage | Property grounds

8. Wessex View

Wessex View
3.5 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Stunning view, great location. We loved the property so much we booked to go again as soon as we got home. Looking forward to our next trip!"
United Kingdom
Kimberley
Wessex View
Exterior

9. Badgers Cottage

Badgers Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Nice"
United Kingdom
Neil
$586 nightly
The price is $703
Aug 28 - Aug 29
Total with taxes and fees
Badgers Cottage
Terrace/patio

10. Ash Corner Cottage

Ash Corner Cottage
2.0 star property
Overcombe
$1,018 nightly
The price is $1,221
Aug 28 - Aug 29
Total with taxes and fees
Ash Corner Cottage
Marina

11. Brewery View

Brewery View
2.0 star property
Weymouth
$518 nightly
The price is $622
Aug 7 - Aug 8
Total with taxes and fees
Brewery View
Beach nearby

12. Flat 6, Thornlow Heights

Flat 6, Thornlow Heights
3.0 star property
Weymouth
$564 nightly
The price is $677
Aug 11 - Aug 12
Total with taxes and fees
Flat 6, Thornlow Heights
2 bedrooms, WiFi (free), individually decorated, individually furnished

13. 26 High West

26 High West
3.0 star property
Weymouth
9.0 out of 10, Wonderful, (2 reviews)
"2nd stay, house on a side road just up from the harbour with free parking if you are lucky, but parking nearby is £6.30 in a car park very close if you are unlucky and cannot park outside. House is comfortable without being stuffy, has all mod cons and a small backyard for smokers or eating breakfast on a warm day. No doubt we will return in the near future."
United Kingdom
Robert
$455 nightly
The price is $546
Aug 6 - Aug 7
Total with taxes and fees
26 High West
Marina

14. Day Cottage

Day Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"The cottage was absolutely excellent , clean, had everything you need,cosy, couldn’t ask for more ,also not far from the beach "
United Kingdom
Cindy
$452 nightly
The price is $542
Aug 24 - Aug 25
Total with taxes and fees
Day Cottage
Dining

15. Sunningdale Rise

Sunningdale Rise
3.0 star property
Overcombe
$1,272 nightly
The price is $1,527
Aug 7 - Aug 8
Total with taxes and fees
Sunningdale Rise
Dining

16. Anchor Cottage

Anchor Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Very nice cottage. Very clean, and a lovely stay."
United Kingdom
Carolyn
$532 nightly
The price is $638
Aug 10 - Aug 11
Total with taxes and fees
Anchor Cottage
Cottage | 3 bedrooms, WiFi (free), individually decorated, individually furnished

17. Wey Cottage

Wey Cottage
3.5 star property
Weymouth
$515 nightly
The price is $617
Aug 29 - Aug 30
Total with taxes and fees
Wey Cottage
Property grounds

18. Victoria House

Victoria House
3.0 star property
Weymouth
$575 nightly
The price is $690
Aug 6 - Aug 7
Total with taxes and fees
Victoria House
Marina

19. Harbour Retreat

Harbour Retreat
3.0 star property
Weymouth
$499 nightly
The price is $598
Aug 22 - Aug 23
Total with taxes and fees
Harbour Retreat
Exterior

20. Weyside

Weyside
2.0 star property
Weymouth
$755 nightly
The price is $906
Aug 5 - Aug 6
Total with taxes and fees
Weyside
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Upwey Hotel Reviews

Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

10/10 Excellent
"What a beautiful hotel !! The staff was so lovely and helpful and the sizing of the rooms the utilities was all perfect !"
Rhian 1-night trip
Posted 5 hours ago
Best Western Weymouth Hotel Rembrandt

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 $475 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?

Quiet location, short walk to beach, with views of Portland and Jurassic coast: Visitors like this Upwey vacation home rental. It is located on the waterfront and has a balcony, a terrace, and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and a selection of books.

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 Durdle Door and Lodmoor Country Park.

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.