Upwey Vacation Rentals : Short-Term Rentals for 2025

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Vacation Rentals in Upwey

Signature Chalet, 3 Bedrooms, Accessible, Sauna

"The property was clean. Just the beds were single Beds in all couple rooms. Would be great if they had double beds instead. "

"Lovely airy cottage - exactly as it looks on the website.Perfect for a quiet retreat."

"The property was a beautifully quaint cottage very clean and had everything we needed. Definitely recommend it."

"Brilliant stay as before. Fantastic, welcoming hosts and beautiful comfortable accommodation "

"We came for a short break Thursday-Sunday. The van was spotless. The host thought about everything from providing fairy liquid, to loo rolls. Even a little sewing kit in the bathroom. We were very lucky with our weather even had a coffee on the veranda. The views over to chesil very pretty at night with the lights. Would highly recommend and use again. Thank you. "

Superior House, 4 Bedrooms, Hot Tub, Garden View

"A lovely venue for a few days R&R in this part of Dorset. The accommodation is modern, spacious and of good quality, with great on-site facilities (pool, sauna, etc). Recommended."

"we came friday after noon the flat was easy to find we had a lovely time the flat was lovely the sea veiw fabulous clean light and lovely and warm and even the weather was good westbay is a joy and my ageing mother and german shepard was happy "

"The views are amazing. Walking path and the sea right behind house. View after view. Well equipped kitchen with tons of space, comfy living room- and I loved the sunroom out back! This was October weather with occasional rain and wind. Must be truly amazing in summer with outdoor spaces.. convenient for Dorset exploring."

"Lovely host, well presented and loved the fact it had a bbq. Travel cot provided which helped good communication with host. "

"Set in isolated rural village with lovely views and walks. Our vist was marred by horrendous wet weather,but we made the best of it. Mark and Madeline were lovely people who made us welcome and dealt with any issues and gave advice about the area."

"We have had an amazing weekend at this beautiful property which is spacious, comfortable, quirky and full of home comforts. Everything you need is here and Wareham was a delight…we had fun in Wareham pottery painting at Pottery Corner and an amazing meal at The Italian Kitchen. Thank you so much. "

"Good communication with Suzanne. House was well equipped and comfortable. Location was perfect for us … close to the cycle path into Weymouth and over to Portland. "

"Excellent family house for celebrating a70th and 40th birthdays . The owners were very generous with the heating. "

"Clean bright and fully equipped if you like cooking."

"The cottage has all the facilities you might need, and the Welcome Box of goodies was a nice touch. The heating came on morning and evening and warmed the cottage very well. We didn't need to use the log fire. The Spar shop, located a minute's walk away, was very useful. I can recommend this accommodation to anyone thinking about a holiday to short break in Dorset. "

1 bedroom, travel crib, WiFi, bed sheets

"Thank you for a perfect stay - the apartment was beautiful; from the beautiful interior of the cosy cushions and throws to the plants hanging at the window. Everything had been thought of in the kitchen and bathroom and having lots of hanging space in the hallway was a huge bonus. The location is ideal - a few minutes walk from the station in one hour direction and the beach in the other. My son and I had a lovely stay - thank you! beach"

"This apartment was amazing ,very clean and equip with everything you needed. I would definitely stay here again. "

"Very happy with the property. It was a good size for our group to share meals. A lovely circular walk on the doorstep and very nearby chalk stream. A bit of a drive to local coast. It’s near a noisy road which you can’t see but you can’t hear it at all from inside the house. "

"We had a lovely stay over New Year in this very cosy character cottage in a perfect location just off the high street in Bridport, a short walk to all the pubs and shops (but very quiet, being in a small lane tucked in behind the high street)). Susan is very communicative and is quick to reply to any queries. Would definitely stay again."

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"Our stay was perfect it was comfortable and relaxing the staff were polite and helpful will defibe staying there again"

CA $169 total

includes taxes & fees

May 1 - May 2

"Very clean and tidy, sea view, helpful staff, hopefully will return later in the year"

CA $106 total

includes taxes & fees

Apr 21 - Apr 22

"Nice acomodating staff! "

CA $128 total

includes taxes & fees

Apr 21 - Apr 22

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Upwey vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upwey vacation rentals we have selected for you start as low as per night. Entering your travel dates in the search wizard 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.

Upwey Vacation Rental Travel Info

Number of vacation rentals	62
Popular accommodation	Upwey cottages
Known landmarks	Weymouth Beach, Chesil Beach and Weymouth Pavilion
International airport	Bournemouth (BOH-Bournemouth Intl.)

Recent reviews of Upwey properties

5/5 Excellent

"Perfect place to stay. Very good gluten free options for dinner. Very quite No road noise air conditioning. And good shower. Very nice sized rooms "

A verified traveller from Maidstone stayed at The Frampton Arms

Posted 1 day ago

5/5 Excellent

Fishing trip

"Lovely experience, been to west bexington a few times but never stayed but now i have i wouldnt stay anywhere else. Lovely staff nice breakfast and a nice comfortable bar to unwind in the evening. As we were there for a fishing trip was ideal for access to the beach and so peaceful at night so a good sleep was great."

A verified traveller stayed at The Manor House

Posted 3 days ago

5/5 Excellent

A delightful place to stay in Dorchester

"Having booked our parking through Just Park, we received excellent directions to the limited spaces at the rear of the hotel. (The satnav wanted to send us elsewhere!) We were welcomed, offered assistance with our baggage and directed to our room. We had selected a Superior Room as we were celebrating an anniversary and found ourselves (after a long and winding walk along a corridor whose floor was a little uneven in places - showing the history of the building) in a suite! Very nice (although the sofa is not particularly comfortable to sit on). The bedroom was large, with a very comfortable bed, a desk a chair and plenty of drawers to store your clothes. The ‘wardrobe’ is off the sitting area. 2 very large TVs and a lovely, large, well appointed bathroom. It suited us very well. No breakfast, but plenty of advice on options nearby. On checkout, I discovered that, although the message I had received from Hotels.com had stated (as per my selection on booking) that I would pay at the hotel, payment had been taken 2 days previously. It was explained that this was the policy of the hotel. I have no problem with this - but I do think that Hotels.com should reflect this in their booking confirmation. All in all, it suited us very well."

A verified traveller stayed at Sleeping Bear Hotel Dorchester

Posted 6 days ago

5/5 Excellent

"The property was in character with the area and is in itself a fine building. Interesting inside with its multi-levels. Staff and service was excellent - all very helpful and attentive. Lucky with the weather sitting outside looking across the square was really great and our party of 10 had a very relaxed and interesting stay."

A verified traveller stayed at The Duchess of Cornwall Inn

Posted 6 days ago

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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?

The Victorian Barn self catering holidays with pool & hot tubs: You might want to consider this vacation home rental near Upwey, which is located in a rural location and has an indoor pool, a patio, and free WiFi to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a dishwasher, and a stovetop. It offers a terrace, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Upwey?

Choose from 3 Expedia vacation rentals in Upwey for a memorable vacation.

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 Area of Outstanding Natural Beauty. In the larger area, you’ll find Durdle Door 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.

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Upwey Vacation Rentals

Check prices for these dates

Vacation Rentals in Upwey

The Dorset Resort

The Dorset Resort

The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

Beautiful, family friendly Cottage with sea views of Chesil Beach

Beautiful, family friendly Cottage with sea views of Chesil Beach

Self Contained Garden Studio With Private Decked Terrace, close to town and sea

Self Contained Garden Studio With Private Decked Terrace, close to town and sea

Luxury mobile home with spectacular sea views.

Luxury mobile home with spectacular sea views.

The Victorian Barn self catering holidays with pool & hot tubs

The Victorian Barn self catering holidays with pool & hot tubs

Apartment with stunning Sea View

Apartment with stunning Sea View

Apartment on Weymouth beachfront

Apartment on Weymouth beachfront

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach

Hidden Retreat - 4 mins to beach & 3 mins to train station. Pet friendly!

Hidden Retreat - 4 mins to beach & 3 mins to train station. Pet friendly!

Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset

Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset

Beautiful large Georgian house with a big garden. Perfect for a family or two!

Beautiful large Georgian house with a big garden. Perfect for a family or two!

Quiet location, short walk to beach, with views of Portland and Jurassic coast

Quiet location, short walk to beach, with views of Portland and Jurassic coast

Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)

Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)

Delightful country cottage. Stunning views. A few minutes walk to Seatown beach

Delightful country cottage. Stunning views. A few minutes walk to Seatown beach

Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town

Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town

Peacehaven Retreat - 4 minutes from the beach! Pet friendly!

Peacehaven Retreat - 4 minutes from the beach! Pet friendly!

Beachside, stunning apartment with sea and harbour views

Beachside, stunning apartment with sea and harbour views

Gorgeous thatched cottage in Purbeck - ideal for family holidays

Gorgeous thatched cottage in Purbeck - ideal for family holidays

Characterful 18th century cottage in Bridport close to the Jurassic Coast.

Characterful 18th century cottage in Bridport close to the Jurassic Coast.

Other types of properties in Upwey you may be interested in

Best Western Weymouth Hotel Rembrandt

Best Western Weymouth Hotel Rembrandt

Fairhaven Hotel

Fairhaven Hotel

The Jubilee Hotel East- with Spa Facilities

The Jubilee Hotel East- with Spa Facilities

Find out more about Upwey

Find out more about Upwey

Upwey Vacation Rental Travel Info

Recent reviews of Upwey properties

Recent reviews of Upwey properties

The Frampton Arms

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Trending destinations on Expedia.ca

Frequently asked questions