Upwey Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Upwey vacation rentals

Beach nearby

The Grain Store

The Grain Store
3.0 star property
Weymouth
The price is P51,226
P61,472 total
includes taxes & fees
May 30 - May 31
The Grain Store
Beach

Braiders Rest

Braiders Rest
3.0 star property
Bridport
The price is P35,492
P42,590 total
includes taxes & fees
May 30 - May 31
Braiders Rest
Dining

Sunningdale Rise

Sunningdale Rise
3.0 star property
Overcombe
The price is P84,954
P101,945 total
includes taxes & fees
Jun 6 - Jun 7
Sunningdale Rise
Beach nearby

74 Reap Lane

74 Reap Lane
3.0 star property
Portland
The price is P32,547
P39,056 total
includes taxes & fees
Jun 6 - Jun 7
74 Reap Lane
Outdoor dining

Littlesea Holiday Park - Holiday Accommodation 19270

Littlesea Holiday Park - Holiday Accommodation 19270
2.5 star property
Weymouth
The price is P27,448
P32,937 total
includes taxes & fees
May 30 - May 31
Littlesea Holiday Park - Holiday Accommodation 19270
Interior

Mill House

Mill House
3.0 star property
Dorchester
The price is P94,409
P94,409 total
includes taxes & fees
May 31 - Jun 1
Mill House
Interior

Tithe Barn Cottage

Tithe Barn Cottage
2.0 star property
Dorchester
The price is P40,501
P48,602 total
includes taxes & fees
Jun 2 - Jun 3
Tithe Barn Cottage
Beach nearby

Betty's Buoy

Betty's Buoy
2.0 star property
Weymouth
The price is P29,776
P35,731 total
includes taxes & fees
Jun 12 - Jun 13
Betty's Buoy
Exterior

Bracken Cottage

Bracken Cottage
2.0 star property
Weymouth
The price is P31,752
P38,102 total
includes taxes & fees
Jun 7 - Jun 8
Bracken Cottage
Interior

Jay Cottage

Jay Cottage
3.5 star property
Weymouth
The price is P26,037
P31,244 total
includes taxes & fees
Jun 6 - Jun 7
Jay Cottage
Living area

Groves House

Groves House
3.0 star property
Portland
Groves House
Beach

Fairways

Fairways
2.0 star property
Weymouth
Fairways
Fridge, dishwasher, electric kettle, toaster

Half Pint Cottage

Half Pint Cottage
3.0 star property
Beaminster
10.0 out of 10, Exceptional, (1 review)
"We stayed here for 3 nights, the property was spotlessly clean on arrival. Parking at the cottage was a blessing as the road outside was busy with residents cars. An ideal base to explore Dorset, and several pubs within easy walking distance. Would stay here again."
United Kingdom
nikki
The price is P30,482
P36,578 total
includes taxes & fees
Jun 6 - Jun 7
Half Pint Cottage
Interior

The Shambles

The Shambles
3.5 star property
Portland
The price is P43,747
P52,496 total
includes taxes & fees
May 30 - May 31
The Shambles
Beach

Agua de Plata, 16 Wakeling Island, Silverlake

Agua de Plata, 16 Wakeling Island, Silverlake
3.0 star property
Dorchester
The price is P57,153
P68,584 total
includes taxes & fees
May 30 - May 31
Agua de Plata, 16 Wakeling Island, Silverlake
Interior

Admiral's Quarter Apartment 5

Admiral's Quarter Apartment 5
3.0 star property
Weymouth
Admiral's Quarter Apartment 5
Interior

Harbour Reach 6

Harbour Reach 6
3.0 star property
Weymouth
The price is P27,307
P32,768 total
includes taxes & fees
May 30 - May 31
Harbour Reach 6
Interior

Pebbles Reach

Pebbles Reach
3.5 star property
Portland
Pebbles Reach
Outdoor spa tub

Anchor House

Anchor House
3.0 star property
Weymouth
The price is P95,750
P114,900 total
includes taxes & fees
May 31 - Jun 1
Anchor House
Outdoor dining

Two @ No36

Two @ No36
3.0 star property
Weymouth
The price is P45,088
P54,105 total
includes taxes & fees
Jun 5 - Jun 6
Two @ No36
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upwey Hotel Reviews

Fairhaven Hotel

Fairhaven Hotel

10/10 Excellent
"Superb location, amazing views of the bay and a short walk to pretty much everything that Weymouth has to offer. The room was clean and tidy, and well stocked with a variety of refreshments (tea, coffee and milk portions). The hotel offers discounted parking with the Q Park at Commercial Road which is worth having (no need to pre-book). I'd happily book another stay here in the future."
David 2-night trip
Posted 2 hours ago
Fairhaven Hotel

Find out more about Upwey

Search for holiday rentals in Upwey on Expedia! You can easily find your home rentals, villas, holiday apartments in Upwey using one of the methods below:

  • View our selection of featured holiday rentals in Upwey
  • Use the map to find apartments and other holiday homes in the Upwey neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Upwey while they last

Look no further and take a look at our great range of rental properties in Upwey!

Explore a world of travel with Expedia

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’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.