Upwey Cottages
246 properties found
246 properties found

123 On The Sea - The Eaves
Weymouth, Dorset
123 On The Sea – The Eaves is a delightful apartment resting in Weymouth, Dorset, featuring beach views, off-road parking, and nearby attractions.
- Wifi
- Baby Friendly
- Dishwasher
- Off Road Parking
for 7 nights
£445

123 On The Sea - Victoria’s Place
Weymouth, Dorset
123 On The Sea – Victoria’s Place is a beautifully appointed seafront apartment in Weymouth, Dorset, featuring beach views, private parking, and a bright open-plan layout.
- Wifi
- Baby Friendly
- Dishwasher
- Off Road Parking
for 7 nights
£515

Little Retreat
Upwey, Dorset
One bedroom, village of Upwey, close to Weymouth.
- Wifi
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
for 7 nights
£485

Little Brook
Nottington near Weymouth, Dorset
A charming, stone-built property resting within the village of Nottington, Dorset.
- Wifi
- EV Charging
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
for 7 nights
£552

Sixpenny Cottage
Upwey, Dorset
A beautiful cottage, located in a pretty village near to Weymouth, with private parking and wifi.
- Wifi
- Baby Friendly
- Washing Machine
for 7 nights
£486

Blue Waters
Weymouth, Dorset
A delightful, one-bedroom holiday home resting in Weymouth, Dorset.
- Wifi
- Dishwasher
for 7 nights
£760

123 On The Sea - The Cubby
Weymouth, Dorset
The Cubby is a delightful first-floor apartment in Weymouth, Dorset, boasting a central location close to shops, pubs, beaches and coastal attractions.
- Wifi
- Dishwasher
for 7 nights
£468

4 The Beaches
Weymouth, Dorset
4 The Beaches is a delightful beach view apartment in Weymouth, Dorset, featuring sea views, a furnished balcony, parking permit, and beachside appeal throughout.
- Wifi
- Dishwasher
- Washing Machine
for 7 nights
£601

Ocean Retreat
Weymouth, Dorset
An arresting apartment set on the shores of Weymouth, Dorset.
- Wifi
- Dishwasher
- Washing Machine
for 7 nights
£773

Riverhouse Lodge
Upwey, Dorset
A stunning holiday lodge found on the outskirts of the beautiful area of Dorset AONB.
- Wifi
- Baby Friendly
- Dishwasher
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
for 7 nights
£385

Fountain Cottage
Weymouth, Dorset
A delightful cottage with charm and character but a modern touch.
- Wifi
- Baby Friendly
- Dishwasher
- Ground Floor Bedroom
- Off Road Parking
- Washing Machine
for 7 nights
£512

Red Rose Apartment
Weymouth, Dorset
Red Rose Apartment is a well-appointed apartment in Weymouth, Dorset and offers guests centrally located space, parking, sea views and the beach close by.
- Wifi
- Washing Machine
for 7 nights
£719

Embassy
Brewers Quay Harbour, Dorset
Embassy is a wonderful, third-floor apartment in Weymouth, Dorset.
- Wifi
- Dishwasher
- Washing Machine
for 7 nights
£485

5 The Beaches
Weymouth, Dorset
A modern second-floor apartment in the popular Dorset resort of Weymouth.
- Wifi
- Dishwasher
for 7 nights
£511

The Secret Courtyard
Weymouth, Dorset
The Secret Courtyard is a welcoming ground-floor apartment in Weymouth, Dorset, featuring contemporary styling, a bright kitchen and enclosed courtyard.
- Wifi
- Ground Floor Bedroom
- Washing Machine
for 7 nights
£569

The Loft @ No36
Weymouth, Dorset
The Loft @ No36, a contemporary, third-floor apartment situated in the heart of Weymouth in Dorset, enjoying sea views with the bech on your doorstep.
- Wifi
- Off Road Parking
for 7 nights
£502

Angel Cottage
Weymouth, Dorset
This charming one-bedroom property resides in Weymouth, Dorset.
- Wifi
for 7 nights
£317

Number 3 by the Sea
Weymouth, Dorset
Number 3 by the Sea is a lovely ground‑floor apartment located in Weymouth, Dorset, boasting sea views, a front patio and direct access to the beach.
- Wifi
- Ground Floor Bedroom
- Off Road Parking
for 7 nights
£518

Bella Rosa
Preston, Dorset
Bella Rosa is a practical house in Overcombe, Dorset, featuring an en-suite bedroom, parking, and easy access to Dorset's beaches and amenities.
- Wifi
- Ground Floor Bedroom
- Washing Machine
for 7 nights
£517
Upwey is a beautiful little village nestled alongside the river Wey. Although it’s now part of Weymouth, Upwey has most definitely retained its village charm with everything you need for a wonderfully relaxing countryside retreat.
Walking through Upwey will take you past some beautifully unique houses and then through areas of completely open countryside. It is so tranquil and pretty that a break in a holiday cottage here will ensure that you leave completely relaxed.
It may be a small village, but Upwey is well known for its Wishing Well and Water Gardens. It is alleged that while unwell and staying in Weymouth, King George III would drink the water from the well, believing it to aid his recovery!
Upwey Wishing Well Tea Rooms is the perfect place for afternoon tea. They are big advocates of all things local so the ingredients they use are all of the finest quality from local Dorset producers. Stock up on the beautifully wrapped homemade jars of chutney and pickles to take back to your cottage to accompany your cheese and wine for the evening!
Upwey is home to some beautiful water gardens around the wishing well and it’s glorious here when the sun shines. Pick a spot for a picnic or just keep meandering along the garden pathways to see a new water garden, pond or waterfall at every turn. Don’t forget to make a wish at the wishing well before you leave!
Upwey even has its own 17th century traditional village pub, The Old Ship. It has a huge roaring fire to sit beside during the colder months and it lovingly welcomes well behaved dogs.
You really are in a fantastic location if you choose one of our Upwey holiday cottages. It feels like a world away from anywhere and almost has a ‘back in time’ feel about it, yet you are just 4 miles away from the award winning, golden sands of Weymouth beach, bustling Weymouth Harbour, superb restaurants and pubs and some great shopping. Weymouth is famous for putting on some fantastic events too! Weymouth Harbour plays host to the Wessex Folk Festival every year in June and Weymouth Carnival take place every August. If champagne and seafood takes your fancy, try the Dorset Seafood Festival, also in Weymouth Harbour in July.
A drive ten minutes inland from Upwey will take you to the wonderful market town of Dorchester. Head here for some great shopping, stunning architecture, Michelin starred restaurants and, if you are there for August bank holiday, try the annual French Market, where you can stock up on fine chocolates, baguettes, cheese and crepes.
You really can’t go wrong by choosing an Upwey holiday cottage for your break. We have some really beautiful Upwey self-catering holiday cottages to choose from. Be sure to check when booking if they are dog friendly, if you are bringing your four legged friend.

