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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sept - 28 Sept

Browse Select Upwey Holiday Homes

Quiet location, short walk to beach, with views of Portland and Jurassic coast
Overlooking a serene pebble beach, this property offers a tranquil coastal retreat.

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

10.0 out of 10, Exceptional, (99)
"The location was great for the sailing, the house met all expectations - clean, good facilities, well kitted out. "
Quiet location, short walk to beach, with views of Portland and Jurassic coast
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Enjoy the view from the spacious conservatory with a triangular roof, and relax on the balcony with a sofa and chairs.

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

10.0 out of 10, Exceptional, (47)
"An excellent property in a great location."
Blue Horizons with uninterrupted Panoramic sea views 2 mins walk from beach
Farmhouse Annexe For 2 People In A Peaceful Location In North Dorset
Escape to a serene garden oasis with lush greenery and vibrant flowers.

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

9.8 out of 10, Exceptional, (55)
"Thoroughly enjoyed our stay in this well equipped accommodation in a a lovely rural setting."
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!
Enjoy a peaceful outdoor space with a table and chairs, surrounded by lush plants and a large tree providing shade.

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

10.0 out of 10, Exceptional, (71)
"Big house more then fully equipped and a very nice yard, walking distance to everything in town."
Beautiful large Georgian house with a big garden. Perfect for a family or two!
The Victorian Barn self catering holidays with pool & hot tubs
Exclusive House, 4 Bedrooms, Hot Tub, Garden Area | Dining room

The Victorian Barn self catering holidays with pool & hot tubs

4.0 star property
9.0 out of 10, Wonderful, (4)
"We stayed in Helena, it was very clean and well equipped. Concern about escape routes in the event of a fire. Some rooms didn’t have a large enough window to get out of. Swimming pool great, as was the hot tub. Lovely setting near Blandford. Would recommend getting shopping delivered as quite remote. "
The Victorian Barn self catering holidays with pool & hot tubs
Beautiful, family friendly Cottage with sea views of Chesil Beach
Enjoy a serene beach experience with gentle waves and scenic views of a nearby town.

Beautiful, family friendly Cottage with sea views of Chesil Beach

9.6 out of 10, Exceptional, (20)
"Great little cottage, within walking distance of the beach. Great host "
Beautiful, family friendly Cottage with sea views of Chesil Beach
Farm House in stunning Dorset countryside with Hardy views
Traditional stone building with a steeply pitched roof, set amidst lush greenery.

Farm House in stunning Dorset countryside with Hardy views

10.0 out of 10, Exceptional, (1)
"Great comms and lovely welcome from Luba and Chris for our two night stay. Easy to find and parking right next to the front door. The cottage was spotlessly clean and very peaceful with two spacious doubles, both with their own TV and modern en-suite facilities. Comfortable lounge with wood burner, TV and jigsaw ready to go - all with lovely views over to Hardy's Monument. Ideal location for visiting the local area by car - we went to Weymouth (Catch! restaurant was fab), Dorchester, Poundbury,...
The price is £172
includes taxes & fees
25 Aug - 26 Aug
Farm House in stunning Dorset countryside with Hardy views
Barn conversion, quiet location and heated swimming pool ( from mid May)
Stunning stone building with a symmetrical facade, featuring two doors and a large arched window.

Barn conversion, quiet location and heated swimming pool ( from mid May)

9.4 out of 10, Exceptional, (60)
"Fantastic property. Great location. Clean, with all the necessary facilities and utilities."
Barn conversion, quiet location and heated swimming pool ( from mid May)
4 bedroom accommodation in Weymouth
Exterior

4 bedroom accommodation in Weymouth

9.4 out of 10, Exceptional, (15)
"Good comfortable house conveniently situated close to town, beach and all local facilities. "
4 bedroom accommodation in Weymouth
Historical, Characterful, Converted Old School House
Traditional stone house with a classic arched doorway and steeply pitched roof, set amidst a well-maintained garden.

Historical, Characterful, Converted Old School House

9.0 out of 10, Wonderful, (2)
"Very nice clean well furnished"
Historical, Characterful, Converted Old School House
Foxearth - sleeps 4 guests in 2 bedrooms
Stroll through our beautifully maintained garden, featuring a variety of plants and flowers.

Foxearth - sleeps 4 guests in 2 bedrooms

Foxearth - sleeps 4 guests in 2 bedrooms
Bay View Luxury Stays - Mount Pleasant, 6 bed with indoor pool
Enjoy meals with friends and family in this stylish dining area, featuring a long table and comfortable seating for six.

Bay View Luxury Stays - Mount Pleasant, 6 bed with indoor pool

10.0 out of 10, Exceptional, (8)
"The property is done up to a really high standard and was ideal for our group. Great Facilities, kids had a blast Location is fabulous"
Bay View Luxury Stays - Mount Pleasant, 6 bed with indoor pool
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Experience the majestic natural rock formation and serene beach with its pebbles and sand.

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

10.0 out of 10, Exceptional, (1)
"A wonderful experience - THANK YOU!"
The price is £285
includes taxes & fees
1 Sept - 2 Sept
Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World
Comfy 2 bed house at Wareham train station; the ‘Gateway to the Purbecks’
Situated at the coast, this natural rock formation features a prominent archway with the sea visible through it.

Comfy 2 bed house at Wareham train station; the ‘Gateway to the Purbecks’

10.0 out of 10, Exceptional, (9)
"A nice house, with all the modern equipment and furnishings. We had a very pleasant and relaxing stay and would happily visit again!"
Comfy 2 bed house at Wareham train station; the ‘Gateway to the Purbecks’
Private detached cottage to rent on Chesil Beach
Enjoy meals with a view of the sea from this dining area, featuring a table for four and a large window.

Private detached cottage to rent on Chesil Beach

10.0 out of 10, Exceptional, (66)
"Stunning location. The house was perfect for a proper break away from it all. Walks, beach fishing and plenty of places to visit nearby."
Private detached cottage to rent on Chesil Beach
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Enjoy cooking in this kitchen with a central island, coffee maker, double oven, and dishwasher.

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

9.8 out of 10, Exceptional, (35)
"Eleven of us 8 adults and 3 children had a lovely time. We stayed for 3 nights. The farmhouse had everything you needed and the views were wonderful Will try to go back"
Self-Catering Farmhouse Cottage set in the Dorset Countryside (Pet Friendly)
Grove Lodge - sleeps 11 guests in 6 bedrooms
Beach nearby

Grove Lodge - sleeps 11 guests in 6 bedrooms

Grove Lodge - sleeps 11 guests in 6 bedrooms
A charming seaside cottage 5 minutes walk from beach on Jurassic Coast
Relax and socialize in this inviting patio area, featuring wicker furniture, a potted plant, and a coffee table perfect for enjoying a drink.

A charming seaside cottage 5 minutes walk from beach on Jurassic Coast

9.2 out of 10, Wonderful, (34)
"Very good property, it suited all of our needs"
The price is £696
includes taxes & fees
22 Aug - 23 Aug
A charming seaside cottage 5 minutes walk from beach on Jurassic Coast
Sunny Barn Stay, Hot Tub & Rural Views – Leopold at The Victorian Barn Dorset
Relax in a hot tub on the patio, surrounded by a grassy field and a gravel path.

Sunny Barn Stay, Hot Tub & Rural Views – Leopold at The Victorian Barn Dorset

10.0 out of 10, Exceptional, (2)
"Lovely location, beautiful and spacious cottage! thank you"
Sunny Barn Stay, Hot Tub & Rural Views – Leopold at The Victorian Barn Dorset
Sea-Esta – A Stylish Coastal Retreat in the Heart of Weymouth
6 bedrooms, iron/ironing board, travel cot, WiFi

Sea-Esta – A Stylish Coastal Retreat in the Heart of Weymouth

Sea-Esta – A Stylish Coastal Retreat in the Heart of Weymouth
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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Top Upwey Hotel Reviews

The Cumberland

The Cumberland

10/10 Excellent
"Nice room with balcony. Good service at brrakfast. "
Milan 2-night trip
Posted 1 day ago
The Cumberland