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

Upwey Vacation Rentals

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Our top choices for Upwey vacation rentals

1. The Sailors Studio|Sleeps2|Weymouth Beach|

The Sailors Studio|Sleeps2|Weymouth Beach|
Weymouth Town Center
10.0 out of 10, Exceptional, (1 review)
The price is CA $103
CA $244 total
includes taxes & fees
Oct 25 - Oct 26
The Sailors Studio|Sleeps2|Weymouth Beach|

2. Hardy View Farm House

Hardy View Farm House
Dorchester
10.0 out of 10, Exceptional, (3 reviews)
"Absolutely Fabulous Stay at this Farmhouse. Wonderful hosts in Luba and Chris who were so informative and helpful.Lovely property inside and out. So relaxing and peaceful. Missing the wonderful breakfasts already. 10 out of 10 !!"
Australia
Carol S.
The price is CA $301
CA $340 total
includes taxes & fees
Oct 28 - Oct 29
Hardy View Farm House

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

Cosy Peacehaven. Free on site Parking! Pet friendly!
Weymouth Town Center
9.4 out of 10, Exceptional, (3 reviews)
"Perfect flat which contained everything we needed for a great stay. It is in an excellent location and parking was a great bonus to us. Communication was great with clear instructions and thoughtful little extras."
United Kingdom
Chloe
The price is CA $147
CA $224 total
includes taxes & fees
Nov 4 - Nov 5
Cosy Peacehaven. Free on site Parking! Pet friendly!

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
The price is CA $690
CA $828 total
includes taxes & fees
Nov 21 - Nov 22
2 Bathsheba Terrace

5. Walkersbase Nutallergy Friendly - Sleeps3 - Petsok

Walkersbase Nutallergy Friendly - Sleeps3 - Petsok
3.0 star property
Bridport
The price is CA $129
CA $268 total
includes taxes & fees
Nov 9 - Nov 10
Walkersbase Nutallergy Friendly - Sleeps3 - Petsok

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

Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Wool
10.0 out of 10, Exceptional, (5 reviews)
"The house was outstanding, probably the best we’ve ever experienced. It is exceptionally clean, comfortable for our family of 5, and convenient to the sites in the area. We would stay there again if we return."
United States
Kristina
The price is CA $169
CA $517 total
includes taxes & fees
Nov 1 - Nov 2
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

7. The Apple House at Moorbath Farm

The Apple House at Moorbath Farm
Bridport
10.0 out of 10, Exceptional, (6 reviews)
"Really nice property ,all nicely finished to a high standard.liked the oak used. We had a nice few days-if you want somewhere peaceful and quiet this is ideal. "
United Kingdom
christopher b.
The price is CA $199
CA $340 total
includes taxes & fees
Nov 17 - Nov 18
The Apple House at Moorbath Farm

8. 1 bedroom accommodation in Ibberton, Blandford Forum

1 bedroom accommodation in Ibberton, Blandford Forum
Ibberton, Blandford Forum
10.0 out of 10, Exceptional, (12 reviews)
"Lovely place, lovely countryside."
United States
Paul Mitchell
The price is CA $276
CA $276 total
includes taxes & fees
Nov 12 - Nov 13
1 bedroom accommodation in Ibberton, Blandford Forum

9. Cosy country cottage for couples

Cosy country cottage for couples
BRIDPORT
9.4 out of 10, Exceptional, (6 reviews)
"We had a great stay ...house was lovely, well equipped & communication was very good with owner."
United Kingdom
Tracey H.
The price is CA $282
CA $445 total
includes taxes & fees
Oct 26 - Oct 27
Cosy country cottage for couples

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

The Old Police House, sleeps 10, 1850,s cottage, Family Stay!
Winterborne Whitechurch
10.0 out of 10, Exceptional, (2 reviews)
"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...
United States
Stacia B.
The price is CA $602
CA $681 total
includes taxes & fees
Oct 31 - Nov 1
The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

11. Battys Barn at Moorbath Farm

Battys Barn at Moorbath Farm
Bridport
10.0 out of 10, Exceptional, (7 reviews)
"Host was very helpful with good communication. The property was very well presented and very clean. It was a really nice stay."
United Kingdom
James A.
The price is CA $353
CA $494 total
includes taxes & fees
Nov 17 - Nov 18
Battys Barn at Moorbath Farm

12. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

2 bedroom accommodation in Glanvilles Wootton, near Sherborne
Glanvilles Wootton, near Sherborne
10.0 out of 10, Exceptional, (30 reviews)
"The accommodation was very spacious and the hospitality was great"
United Kingdom
Caroline H.
The price is CA $645
CA $645 total
includes taxes & fees
Nov 18 - Nov 19
2 bedroom accommodation in Glanvilles Wootton, near Sherborne

13. Sea Spray

Sea Spray
3.0 star property
Overcombe
The price is CA $756
CA $907 total
includes taxes & fees
Nov 11 - Nov 12
Sea Spray

14. 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 CA $911
CA $1,093 total
includes taxes & fees
Nov 4 - Nov 5
The Little Cottage

15. Hide-a-way

Hide-a-way
3.0 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 CA $651
CA $781 total
includes taxes & fees
Nov 6 - Nov 7
Hide-a-way

16. Norden Cottage

Norden Cottage
3.0 star property
Weymouth
6.0 out of 10, (1 review)
"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...
United Kingdom
Hilary
The price is CA $922
CA $1,107 total
includes taxes & fees
Nov 4 - Nov 5
Norden Cottage

17. Cedar Drive

Cedar Drive
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"So clean I could roll around in the property, also very thoughtful of the host, even a fly squatter was available. Would highly recommend if you’re in the area."
United Kingdom
David
The price is CA $818
CA $982 total
includes taxes & fees
Oct 25 - Oct 26
Cedar Drive

18. Badgers Cottage

Badgers Cottage
3.0 star property
Weymouth
10.0 out of 10, Exceptional, (1 review)
"Nice"
United Kingdom
Neil
The price is CA $817
CA $980 total
includes taxes & fees
Nov 18 - Nov 19
Badgers Cottage

19. Flat 6, Thornlow Heights

Flat 6, Thornlow Heights
3.0 star property
Southlands
The price is CA $786
CA $944 total
includes taxes & fees
Nov 3 - Nov 4
Flat 6, Thornlow Heights

20. 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 CA $630
CA $756 total
includes taxes & fees
Nov 12 - Nov 13
Day Cottage
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

Find out more about Upwey

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Upwey. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.