Upwey Vacation Rentals : Short-Term Rentals for 2026

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Our top choices for Upwey vacation rentals

A cozy living room with a green sofa, a dining table set with plates and cups, and a variety of wall art.

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

Weymouth Town Center

Chloe

CA $244 total

includes taxes & fees

Sep 11 - Sep 12

A marina with boats docked, a statue in the foreground, and buildings in the background.

2. The Lighthouse Suite|Sleeps4|Weymouth Beach|

Weymouth Town Center

"Property very difficult to find as out of date pictures & false impression of outside. Property inside was fairly clean. But access stairs & Outlook really let it down as not clean. Apartmentment was well equipped & comfortable. Sadly shower was not working nor was the fan in the bathroom. It is however in a very noisy area late at night & early in the morning, so personally would not stay here with children. However it is very close to all amenities."

Lynn

A bedroom with a bed, pillows, a red blanket, and a window with plants.

3. Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!

Weymouth Town Center

Kim E.

CA $273 total

includes taxes & fees

Sep 13 - Sep 14

A two-story house with a white exterior, a stone wall on the right, and a small garden with potted plants and flowers.

4. The Little Cottage

Weymouth

Lea

CA $1,088 total

includes taxes & fees

Sep 21 - Sep 22

A bathroom with a window, a sink, and two potted plants.

5. Hardy View Farm House

Dorchester

Carol S.

CA $320 total

includes taxes & fees

Sep 9 - Sep 10

A beach with a natural rock arch formation.

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

Wool

Kristina

CA $629 total

includes taxes & fees

Oct 1 - Oct 2

A two-story house with a sloped roof, large windows, and a patio area with outdoor furniture.

7. Cosy cottage for Autumn breaks

Morcombelake

Gary C.

CA $412 total

includes taxes & fees

Sep 13 - Sep 14

A stone house with a thatched-roof extension, a stone well, and a grassy yard.

8. The Apple House at Moorbath Farm

Bridport

christopher b.

CA $377 total

includes taxes & fees

Sep 27 - Sep 28

A small wooden structure with a door and steps leading up to it, surrounded by greenery and a picnic table with cushions.

9. 1 bedroom accommodation in Ibberton, Blandford Forum

Ibberton, Blandford Forum

Paul Mitchell

CA $334 total

includes taxes & fees

Oct 2 - Oct 3

A two-story house with a sloped roof, a front porch with chairs, and a small garden area.

10. Cosy country cottage for couples

BRIDPORT

Tracey H.

CA $436 total

includes taxes & fees

Sep 8 - Sep 9

A brick house with a sloped roof, a patio with a table and chairs, and a garden with various plants.

11. Battys Barn at Moorbath Farm

Bridport

James A.

CA $478 total

includes taxes & fees

Sep 8 - Sep 9

A cozy room with exposed brick walls, wooden beams, and a mix of leather and fabric seating.

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

Winterborne Whitechurch

"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...

Stacia B.

CA $685 total

includes taxes & fees

Sep 16 - Sep 17

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

13. Sea Spray

Overcombe

CA $903 total

includes taxes & fees

Oct 2 - Oct 3

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

14. 2 Bathsheba Terrace

Dorchester

Rachael

CA $823 total

includes taxes & fees

Sep 23 - Sep 24

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

15. Ash Corner Cottage

Overcombe

CA $1,546 total

includes taxes & fees

Sep 21 - Sep 22

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

16. Cedar Drive

Weymouth

David

CA $977 total

includes taxes & fees

Oct 3 - Oct 4

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

17. Coastguard Lookout

Wyke Regis

CA $855 total

includes taxes & fees

Sep 12 - Sep 13

18. Hide-a-way

Weymouth

Kim

CA $777 total

includes taxes & fees

Sep 27 - Sep 28

A waterfront with several boats docked, a row of buildings with various businesses, and a clear sky.

19. Day Cottage

Weymouth Town Center

Cindy

CA $752 total

includes taxes & fees

Sep 10 - Sep 11

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.

20. Bracken Cottage

Weymouth

"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...

michael

CA $875 total

includes taxes & fees

Sep 12 - Sep 13

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Top Upwey Hotel Reviews

The Jubilee Hotel West- with Spa Facilities

10/10 Excellent

"So lovely here the hotel is great all staff are so lovely will defo return next time i will ask for a bath in the bathroom as i did struggle with shower as i have disabilities but it was 2 late for me to get a room like that but thats my fault not theirs.The restaurant in there is on point had a lush steak n garlic mushrooms also crumble for pudding also was lovely and the breakfast was also fab the staff work hard in there and got to say prices at the bar are the best ever and we played bingo and the karaoke was hilarious such a great 2 night break xx"

The Jubilee Hotel East- with Spa Facilities

8/10 Good

"Only spent 1 night there in a small single room in the East wing, exactly as advertised though, small but comfortable bed, good value for money in my opinion. Paid for the buffet breakfast on the day, good value for money though even at the higher rate. Evening in the bar waa quite lively considering the time of year. Would recommend."

Best Western Weymouth Hotel Rembrandt

10/10 Excellent

"We were welcomed by friendly staff, Clare at reception was great. The Hotel was exceptionally clean. The room was well furnished, beds comfortable. Facilities were perfect. Bar and restaurant very comfortable. We had evening meal and breakfast both well cooked and a great variety at breakfast. Bar staff worked hard and remembered our drink choices . We saw a cleaner working in the lobby she was very attentive, the hotel was spotless . The Spa was relaxing. We saw locals comingni to use the pool which says alot for the hotel facilities . Its a flat 5 minute walk to the beachfront. Plenty of parking spaces. Will definitely return."

The Frampton Arms

8/10 Good

"On arrival, mid afternoon on a Saturday, bar tables were not cleared or wiped plus the floor could of done with a good sweep, on booking in we found the room to be of a good standard, we had dinner in the restaurant and the food was excellent, but again on getting refill drinks we had to ask for the used glasses to be removed. Coming down to breakfast Sunday morning, everything was great, the young man on duty making sure tables was cleared and wiped, breakfast items replenished and fresh coffee maintained, Well done him, Sundays roast was good but Monday morning things could of been a lot better, I asked if there was any tea spoons, and one was produced from behind the bar, sadly breakfast items were not replenished , and the area was not kept clean or tidy!!! Well done to the guy who did breakfast Sunday morning, 30/8"

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 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.

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Check prices for these dates

Our top choices for Upwey vacation rentals

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

2. The Lighthouse Suite|Sleeps4|Weymouth Beach|

3. Seaside Escape - Free parking! 4 minutes to the beach! Pet friendly!

4. The Little Cottage

5. Hardy View Farm House

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

7. Cosy cottage for Autumn breaks

8. The Apple House at Moorbath Farm

9. 1 bedroom accommodation in Ibberton, Blandford Forum

10. Cosy country cottage for couples

11. Battys Barn at Moorbath Farm

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

13. Sea Spray

14. 2 Bathsheba Terrace

15. Ash Corner Cottage

16. Cedar Drive

17. Coastguard Lookout

18. Hide-a-way

19. Day Cottage

20. Bracken Cottage

Find vacation rentals that suit your style

Top Upwey Hotel Reviews

The Jubilee Hotel West- with Spa Facilities

Aaran Guesthouse

The Duchess of Cornwall Inn

Heights Hotel

The Jubilee Hotel East- with Spa Facilities

Fairhaven Hotel

Best Western Weymouth Hotel Rembrandt

The Frampton Arms

Sleeping Bear Hotel Dorchester

Find out more about Upwey

Frequently asked questions

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