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Top Holiday Rentals in Upwey

Outdoor dining
The Heart of a Dorset Village
The Heart of a Dorset Village
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.
Fridge, microwave, oven, stovetop
Apartment near the beach with private parking and pet friendly
9.4 out of 10, Exceptional, (14)
"Stayed over the bank holiday weekend. Nice quiet location with a very short walk to Weymouth centre. And the parking space was a bonus! The apartment had everything we needed and we had no problems."
Apartment near the beach with private parking and pet friendly
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Property grounds
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
9.6 out of 10, Exceptional, (109)
"Julia and Paul are great hosts, the welcome pack was useful, the location to Bridport is excellent. This was the third time we have been here and will go again in the future. Thanks to our hosts."
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
Beach nearby
Luxury mobile home with spectacular sea views.
9.8 out of 10, Exceptional, (99)
"Very pleasant"
Luxury mobile home with spectacular sea views.
Fridge, microwave, oven, stovetop
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
9.4 out of 10, Exceptional, (16)
"Lots of room for the kids house was delightfully cool despite the heat-wave Barbecues excellent!!Well equipped for family getaways.Great position for coast & walks .Enjoyed by all!"
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
Sun-loungers
The Hide With Private Wood Fired Hot Tub. A truly romantic getaway on a Vineyard
10.0 out of 10, Exceptional, (47)
"Amazing vineyard views, the hide is done out beautifully with all the pots and pans you need for indoor or outdoor hob or bbq cooking so you need to bring nothing. Wood burners in each room and a fire pit outside for cooking/ marshmallow toasting makes it so cozy! Hot tub is so much fun to heat with the wood burner and so relaxing to look over the vineyard sat with a glass of vino. Completely isolated and so peaceful. hosts are so friendly and helpful. We booked the vineyard tour and cheese and...
The Hide With Private Wood Fired Hot Tub. A truly romantic getaway on a Vineyard
Fridge, microwave, oven, stovetop
Luxury Detached House and Grounds, also benefits from full disabled facilities.
9.4 out of 10, Exceptional, (65)
"Perfect property for our trip with teens, grandparents, extended family and our 2 well behaved dogs. Wonderful space, facilities and views. Host very attentive and excellent communication. We needed somewhere we could access with a wheelchair abd this property was well designed for easy access, a lift and multiple wet rooms. Enjoyed large family dining and quality time in the open planned living space. Highly recommend !"
Luxury Detached House and Grounds, also benefits from full disabled facilities.
Bar (on property)
Weymouth, Dorset - Pebble Bank with stunning views of Chesil Beach
9.4 out of 10, Exceptional, (20)
"Very nice"
Weymouth, Dorset - Pebble Bank with stunning views of Chesil Beach
View from property
No.26 Marina View apartment, parking permit, harbour and Marina views
10.0 out of 10, Exceptional, (5)
"Fabulous location and great accommodation. We were first time visitors to the area and absolutely loved it. The apartment is spacious and well cared for with everything you need for a short stay. Would definitely recommend and we hope to return."
No.26 Marina View apartment, parking permit, harbour and Marina views
Signature Chalet, 3 Bedrooms, Accessible, Sauna | Desk, laptop workspace, blackout curtains, iron/ironing board
The Dorset Resort
4.0 star property
10.0 out of 10, Exceptional, (22)
"Everything was great with our visit! The lodge was easy to locate, immaculate, and the staff at the check in desk were fantastic. Would definitely stay here again! The private sauna in the lodge was brilliant too! Couldn't fault the visit at all"
The Dorset Resort
Fridge, microwave, oven, stovetop
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
9.8 out of 10, Exceptional, (30)
"This is probably the very best holiday accommodation i have ever stayed in. It was clean, spacious and the kitchen was superbly well equipped. The grounds are extensive, wirh beautiful views. We were here in late spring when rhe blossom and birdsong are amazing. We had an age range of 9 to 70 and everybody was happy. The games room got a lot of use! The hosts were pleasant and gracious. A very very big thank you to our hosts. Worth every penny!,"
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Beach
The hideaway with free parking
9.6 out of 10, Exceptional, (5)
"Georgous coach house, beautiful decor and had eveything you needed. It was very clean and just lovely. Annabelle, th host, couldnt have been more helpful. Would love to stay here again."
The hideaway with free parking
Beach nearby, sun-loungers
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
10.0 out of 10, Exceptional, (75)
"The cottage is so comfortable, well-located, and well-equipped. I could not have asked for a better experience. Thank you!"
Ideal quiet beach location for walking/cycling/watersports & Jurassic Coast
Interior
Peacehaven Retreat - 4 minutes from the beach!
10.0 out of 10, Exceptional, (1)
"The apartment was a peaceful haven for us to stay in! Small but cosy, amazing to have a Comfortable bed/sofa bed, tv and coffee machine. It was great to meet the host as soon as we made contact when we needed help- they were very attentive! We found free street parking near by, only 5 minute walk away. The location was very close to the beach /shops so very convenient for our short stay. Thank you for all the homely touches which made the most of the space such as plants and the decor was really...
Peacehaven Retreat - 4 minutes from the beach!
Exterior
Beautiful, family friendly Cottage with sea views of Chesil Beach
9.6 out of 10, Exceptional, (14)
"Had a lovely time good central location. Nice place to stay better than a B&B"
Beautiful, family friendly Cottage with sea views of Chesil Beach
Fridge, microwave, oven, stovetop
Thatched Mid Terraced Cottage
8.0 out of 10, Very good, (3)
"Nice property but very moldy inside. When my son entered he began counting spiders. He stopped at 15 but estimated that there must’ve been 30 spiders in the stairwell and main hallway. Now I like spiders and would never kill one, but I realize that’s not for everyone. I would trap them and put them outside. There was no WiFi. Zero, we connected to the router but that had no connection to the Internet. Also there was very limited cell phone service, so mobile hotspot was spotty. We were...
Thatched Mid Terraced Cottage
Property grounds
escape the ordinary - private self catered group holiday stay
10.0 out of 10, Exceptional, (1)
"We had a lovely long weekend at the Piddle Inn. Downstairs is just like a pub - all for us! Bar, games room and pub kitchen fantastic for a family group. Gorgeous bedrooms and the sound of the stream at night. Lovely walks straight from the back and Alan the host, was incredibly helpful and friendly."
escape the ordinary - private self catered group holiday stay
Superior House, 4 Bedrooms, Hot Tub, Garden View | Egyptian cotton sheets, premium bedding, memory-foam beds
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
Exterior
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
10.0 out of 10, Exceptional, (37)
"Had a really great stay here. House was clean, tidy and modern. Views are fantastic. Will go back"
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Don't see what you're looking for?
See all available properties in Upwey
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.

Upwey Holiday Rental Travel Info

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

Other types of properties in Upwey you may be interested in

Deluxe Quadruple Room, Sea View | Desk, bed sheets
Fairhaven Hotel
2.5 star property
8.8 out of 10, Excellent, (299)
"We were upgraded, on arrival, to a family room with a sea view. The room and the view were excellent. Will definitely return"
The price is £73
includes taxes & fees
16 Jun - 17 Jun
Fairhaven Hotel
Restaurant
Best Western Weymouth Hotel Rembrandt
3.0 star property
8.2 out of 10, Very good, (1000)
"Overall a good stay. Spoilt a little as we stayed previously and didn't have to pay for the pool etc. This time however we did as we booked through Expedia, although we tried to book direct there was no room availability. I think it should be as it says on the best western website,if your a resident then it's all included."
The price is £107
includes taxes & fees
2 Jun - 3 Jun
Best Western Weymouth Hotel Rembrandt
Seaview Double with Sofa Bed | Iron/ironing board, free WiFi, bed sheets
The Jubilee Hotel - with Spa, Restaurant and Entertainment
3.0 star property
7.4 out of 10, Good, (309)
"Had a lovely overnight stay lovely sea view room with our dog great breakfast and very dog friendly "
The price is £119
includes taxes & fees
28 May - 29 May
The Jubilee Hotel - with Spa, Restaurant and Entertainment
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.

Everything you need to know about Upwey holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Upwey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Upwey holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Upwey holiday 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 holiday 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 holiday.

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. 

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?

The Heart of a Dorset Village: This highly rated holiday home rental in Upwey is equipped with 1 hot tub, laundry facilities and WiFi to help you feel comfortable during your stay.

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 Durdle Door and Bowleaze Cove 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.

Recent reviews of Upwey properties
Expedia verified reviews

The Manor House

The Manor House

5/5 Excellent
"Great hotel and great staff. Organized our family event superbly. Food excellent and service perfect."
A verified traveller stayed at The Manor House
Posted 1 day ago
The Manor House