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

Upwey Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

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

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 S$1,001
includes taxes & fees
26 Sept - 27 Sept
The Little Cottage

2. 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 S$715
includes taxes & fees
11 Sept - 12 Sept
Hide-a-way
A spacious living room with a high ceiling, a dining area, and a television on a wooden stand.

3. The Apple Loft at Jordan House

The Apple Loft at Jordan House
3.0 star property
Overcombe
The Apple Loft at Jordan House
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
The price is S$831
includes taxes & fees
2 Oct - 3 Oct
Sea Spray
A harbor with boats docked, a building labeled 'The George Inn', and a cloudy sky.

5. Brewery View

Brewery View
2.0 star property
Rodwell
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 S$795
includes taxes & fees
11 Sept - 12 Sept
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.

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
The price is S$806
includes taxes & fees
12 Sept - 13 Sept
Bracken Cottage
A cozy living room with a grey sofa, a green throw blanket, and a dining area with wicker chairs.

7. 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 S$758
includes taxes & fees
24 Sept - 25 Sept
2 Bathsheba Terrace
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 Town Center
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 S$692
includes taxes & fees
15 Sept - 16 Sept
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 S$1,423
includes taxes & fees
5 Sept - 6 Sept
Ash Corner Cottage
A harbor with boats docked along the waterfront, surrounded by buildings with various storefronts.

10. Harbour Retreat

Harbour Retreat
3.0 star property
Weymouth Town Center
10.0 out of 10, Exceptional, (1 review)
"A very good location and a lovely property. You are in the centre of town so expect some noise. The only downside is the parking. I misunderstood the zone map and got a ticket. When I did understand the map I couldn’t find a space anywhere so use the recommended car park across the river which is reasonably priced. Visit was in May half term and the town was busy on a bank holiday weekend so probably why"
United Kingdom
christian
The price is S$764
includes taxes & fees
15 Sept - 16 Sept
Harbour Retreat
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

Sleeping Bear Hotel Dorchester

Sleeping Bear Hotel Dorchester

10/10 Excellent
"This hotel was in a great location with many nice restaurants on the door step and plenty of history in the town. The staff were so friendly and helpful would definitely stay there again"
Angela 1-night trip
Posted 10 hours ago
Sleeping Bear Hotel Dorchester

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’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 wider area, you’ll find Bowleaze Cove Beach and Osmington Bay 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.