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

Upwey Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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

The Little Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Clean cottage, great location, comfortable beds."
Australia
Lea
The price is P40,767
P48,920 total
includes taxes & fees
Sep 2 - Sep 3
The Little Cottage
A kitchen with a stove, oven, microwave, and a window with a view of cacti.

2. Honeypot Cottage

Honeypot Cottage
2.0 star property
Weymouth
Honeypot Cottage

3. 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
The price is P29,109
P34,931 total
includes taxes & fees
Sep 8 - Sep 9
Hide-a-way
A bedroom with a bed, a wooden chair, a desk with a mirror, and a window with curtains.

4. Sea Spray

Sea Spray
3.0 star property
Overcombe
Sea Spray
A cozy living room with a grey sofa, a green throw blanket, and a dining area with wicker chairs.

5. 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
The price is P30,852
P37,023 total
includes taxes & fees
Sep 24 - Sep 25
2 Bathsheba Terrace
A harbor with boats docked, a building labeled 'The George Inn', and a cloudy sky.

6. Brewery View

Brewery View
2.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Very clean, location great, comfortable and we received regular updates and communication. All very helpful"
United Kingdom
Helen
The price is P32,351
P38,821 total
includes taxes & fees
Sep 2 - Sep 3
Brewery View
A stone building with a thatched roof, multiple windows, and a door. There is a small outdoor seating area with two chairs and a table.

7. 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
The price is P32,840
P39,407 total
includes taxes & fees
Sep 10 - Sep 11
Bracken Cottage
A waterfront with several boats docked, a row of buildings with various businesses, and a clear sky.

8. 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
The price is P28,179
P33,815 total
includes taxes & fees
Sep 3 - Sep 4
Day Cottage
A stone house with a paved patio, a small garden, and a view of the sea.

9. Ash Corner Cottage

Ash Corner Cottage
2.0 star property
Overcombe
The price is P57,932
P69,518 total
includes taxes & fees
Sep 4 - Sep 5
Ash Corner Cottage
A traditional stone building with a thatched roof and a chimney.

10. Badgers Cottage

Badgers Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Nice"
United Kingdom
Neil
The price is P36,547
P43,857 total
includes taxes & fees
Sep 5 - Sep 6
Badgers Cottage
A seaside promenade with colorful buildings, a palm tree, and a beach.

11. 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
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

Aaran Guesthouse

Aaran Guesthouse

10/10 Excellent
"Amazing stay for the night the owners very helpful and kind let us keep our suitcases in the building while we went out, definitely staying again"
Jade 1-night trip
Posted 23 hours ago
Aaran Guesthouse

Find out more about Upwey

Search for holiday rentals in Upwey on Expedia! You can easily find your home rentals, villas, holiday apartments in Upwey using one of the methods below:

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Look no further and take a look at our great range of rental properties in Upwey!

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’s there to see and do in Upwey?

While exploring the area, visit family-friendly sights like SEA LIFE Centre Weymouth, or get outside and enjoy nature at Dorset National Landscape. In the larger area, you’ll find Bowleaze Cove Beach and Osmington Bay 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.