Photo by Sue Wormald

Upwey Holiday Rentals

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Holiday Rentals in Upwey

The Dorset Resort
Signature Chalet, 3 Bedrooms, Accessible, Sauna
The Dorset Resort
4.0 star property
10.0 out of 10, Exceptional, (27)
"The property was clean. Just the beds were single Beds in all couple rooms. Would be great if they had double beds instead. "
The Dorset Resort
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
Property grounds
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
10.0 out of 10, Exceptional, (1)
"Had a wonderful stay on this beautiful boat, extremely clean and tidy with all the amenities you could hope for. Excellent location and lovely marina to enjoy with great facilities. Will definitely be returning again very soon. Very highly recommended."
Sunseeker Renagade 60ft in Weymouth. Perfect to explore the Jurassic Coast.
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Beach nearby, sun-loungers
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
9.8 out of 10, Exceptional, (89)
"It was very clean and all the things there that was needed wih loverly views and surrounding area .i would recommend the stay there."
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Private detached cottage to rent on Chesil Beach
Dining
Private detached cottage to rent on Chesil Beach
10.0 out of 10, Exceptional, (61)
"Back to Greenbanks to get our annual fix. Fab house, fab location, total isolation away from it all."
Private detached cottage to rent on Chesil Beach
Luxury mobile home with spectacular sea views.
Beach nearby
Luxury mobile home with spectacular sea views.
9.8 out of 10, Exceptional, (109)
"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. "
Luxury mobile home with spectacular sea views.
Beachside, stunning apartment with sea and harbour views
Interior
Beachside, stunning apartment with sea and harbour views
9.6 out of 10, Exceptional, (63)
"Came for a short autumn break. Loved it! Great apartment, ideally located for exploring all of the Jurassic coast. Perfectly positioned to either pop down to the beach or to sit on the balcony and enjoy the views and watch the world go by. "
Beachside, stunning apartment with sea and harbour views
Apartment near the beach with private parking and pet friendly
Fridge, microwave, oven, stovetop
Apartment near the beach with private parking and pet friendly
9.4 out of 10, Exceptional, (20)
"Couldn't as for more, clean, lovely little property about 10 mins from the beach and town center."
Apartment near the beach with private parking and pet friendly
Luxury Detached House and Grounds, also benefits from full disabled facilities.
Interior
Luxury Detached House and Grounds, also benefits from full disabled facilities.
9.4 out of 10, Exceptional, (73)
"We absolutely love this gorgeous house. It's really well kitted out, it's clean, it's in a beautiful place and it's so so quiet. We all slept like logs and had a wonderful relaxing time. Thank you so much again."
Luxury Detached House and Grounds, also benefits from full disabled facilities.
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
Exterior detail
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
9.6 out of 10, Exceptional, (123)
"A lovely, cosy cabin with an enclosed decked area, perfect for me & my labrador to have a 4 day getaway. Short walk into town, short drive to the coast. Delightful place."
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
Exterior
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
9.0 out of 10, Wonderful, (42)
"Very nice and i will stay again"
Edwardian House in the Heart of Weymouth 200m from Sandy Beach by the Sea
No.26 Marina View apartment, parking permit, harbour and Marina views
View from property
No.26 Marina View apartment, parking permit, harbour and Marina views
10.0 out of 10, Exceptional, (15)
"All aspects excellent, would recommend without hesitation."
No.26 Marina View apartment, parking permit, harbour and Marina views
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset
Property grounds
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset
9.8 out of 10, Exceptional, (52)
"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."
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset
Peacehaven Retreat - 4 minutes from the beach!
1 bedroom, travel cot, WiFi, bed sheets
Peacehaven Retreat - 4 minutes from the beach!
10.0 out of 10, Exceptional, (2)
"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"
The price is AU$171
includes taxes & fees
16 Nov - 17 Nov
Peacehaven Retreat - 4 minutes from the beach!
Beautiful, family friendly Cottage with sea views of Chesil Beach
Exterior
Beautiful, family friendly Cottage with sea views of Chesil Beach
9.6 out of 10, Exceptional, (17)
"The property was a beautifully quaint cottage very clean and had everything we needed. Definitely recommend it."
Beautiful, family friendly Cottage with sea views of Chesil Beach
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom
Outdoor spa tub
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom
9.6 out of 10, Exceptional, (33)
"We had a lovely stay, the property was clean, spacious and had everything we needed. The location for us was great, if you like walking then highly recommend. Within 40 minutes drive there is a large number of places to visit and the village has everything you need. Pub within a couple of minutes walk as well as shops for supplies. Would happily stay here again."
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom
Thatched Mid Terraced Cottage
Fridge, microwave, oven, stovetop
Thatched Mid Terraced Cottage
8.8 out of 10, Excellent, (5)
"A cosy base with all we needed for a lovely stay in a lovely area. A nice welcome package of flowers, drinks and biscuits, along with a few extras - cooking oil and tea bags. Impressed with the kitchen area, which was well stocked with equipment to enable easy self catering. Denise was a very thoughtful host, willing to respond quickly to questions. One point to note - we didn't want one, but there isn't a hot tub!"
Thatched Mid Terraced Cottage
The Victorian Barn self catering holidays with pool & hot tubs
Superior House, 4 Bedrooms, Hot Tub, Garden View
The Victorian Barn self catering holidays with pool & hot tubs
4.0 star property
9.4 out of 10, Exceptional, (3)
"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."
The Victorian Barn self catering holidays with pool & hot tubs
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Terrace/patio
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
10.0 out of 10, Exceptional, (44)
"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."
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town
Beach nearby
Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town
10.0 out of 10, Exceptional, (49)
"Cottage is exactly as described and very well set up. Lovely design choices that make for a cosy and quiet break away. A lovely welcome box on arrival and prompt responses from the owner both during and before our trip. We would certainly hope to be back atbsome point, thank you!"
Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
Fridge, microwave, oven, stovetop
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
9.6 out of 10, Exceptional, (20)
"Perfect venue for a cosy week catching up with friends, we had been looking for somewhere large enough for all 10 of us to get together, play board games and have a film night! This was perfect! The dining table accomodated us all, as did the sofa! We also did all our own cooking and found the kitchen to be well equiped, (far more so than some professional kitchens weve used!) Will definitely be keeping this saved for future catch ups!!"
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
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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Other types of properties in Upwey you may be interested in

Fairhaven Hotel
Deluxe Quadruple Room, Sea View
Fairhaven Hotel
2.5 star property
8.6 out of 10, Excellent, (499)
"Great location, helpful staff, bar onsite and live music Superior rooms are huge :)"
The price is AU$116
includes taxes & fees
17 Nov - 18 Nov
Fairhaven Hotel
Best Western Weymouth Hotel Rembrandt
Restaurant
Best Western Weymouth Hotel Rembrandt
3.0 star property
8.2 out of 10, Very good, (1002)
"This hotel was lovely and clean and in a quiet location, and it was an easy quick walk to the beach and town. Would recommend."
The price is AU$175
includes taxes & fees
1 Dec - 2 Dec
Best Western Weymouth Hotel Rembrandt
The Jubilee Hotel East- with Spa Facilities
Outdoor spa tub
The Jubilee Hotel East- with Spa Facilities
3.0 star property
7.0 out of 10, Good, (348)
"Some of the staff was very helpful, had a bad experience at the restaurant my table was not clean so requested if they could help me, the staff member gives me a duster and I had to clean it on my own, No cleaning was done of the room on the next day as my bins were full and no towels were refreshed and so I had to request to do so, and soon it was done. Had requested for a room with sea view they replied that it was not available didn’t give any options and there was no reply for the note I...
The price is AU$123
includes taxes & fees
19 Nov - 20 Nov
The Jubilee Hotel East- with Spa Facilities
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.

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 are some of the best holiday rentals that Upwey has to offer?

Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast : This holiday home rental outside of Upwey is located on the waterfront, and has a balcony, a terrace and laundry facilities to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals will I find in Upwey?

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

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