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Upwey Cottages

246 properties found

A wooden front door next to a window with shutters and a gray mailbox numbered 20 at Smugglers Cottage in Weymouth

Smugglers Cottage

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£653

A terrace with table and chair overlooking a street at Harbour Retreat in Weymouth

Harbour Retreat

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£504

A living room with a sofa, chair, coffee table and television at 123 On The Sea – Victoria’s Place in Weymouth
New

123 On The Sea - Victoria’s Place

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£453

A window with champagne and glasses overlooking the sea at 123 On The Sea – The Eaves in Weymouth
New

123 On The Sea - The Eaves

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£453

A stone cottage with a white door and windows a wooden gate and gravel driveway at Little Brook in Nottington near Weymouth

Little Brook

Nottington near Weymouth, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£552

A hallway with door opening to the sea at 123 On The Sea - The Cubby in Weymouth
New

123 On The Sea - The Cubby

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£423

A living room with furniture including a sofa and a dresser at 4 The Beaches in Weymouth
New

4 The Beaches

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£601

A house with a deck and garden at Little Retreat in Upwey

Little Retreat

Upwey, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£485

A garden with grass a wooden deck with a swing and a patio with chairs and a table at Blue Waters in Weymouth

Blue Waters

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£760

A patio with a round table and chairs under a green umbrella surrounded by potted plants and garden furniture at Sixpenny Cottage in Upwey

Sixpenny Cottage

Upwey, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£485

A living room with a grey sofa with colorful cushions a glass coffee table and a fireplace at Ocean Retreat in Weymouth
Offer

Ocean Retreat

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£773

An outside view of a small brick building with a red door and a window with plants and a green utility box at Fountain Cottage in Weymouth

Fountain Cottage

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£495

An outdoor garden area with a gravel path picnic table plastic chairs and trees at Riverhouse Lodge in Upwey

Riverhouse Lodge

Upwey, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£385

A living room with a sofa and dining table at Red Rose Apartment in Weymouth

Red Rose Apartment

Weymouth, Dorset

3 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£776

A small dining area with a round table set for four near a window with a view of the beach and ocean at 5 The Beaches Weymouth

5 The Beaches

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£511

A brick house exterior with white framed windows a door a mailbox and a small outdoor table with a bench at Goliath in Brewers Quay Harbour
Offer

Goliath

Brewers Quay Harbour, Dorset

2 Guests
1 Beds
Pet Friendly
Wifi

for 7 nights

From

£525

A street view of terraced houses with white doors and windows at Angel Cottage in Weymouth

Angel Cottage

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£317

A window looking out onto a harbor with fishing boats and buildings at Embassy Brewers Quay Harbour

Embassy

Brewers Quay Harbour, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£485

A garden with tables and chairs at Beck House in Weymouth
Offer

Beck House

Weymouth, Dorset

4 Guests
2 Beds
No pets
Wifi

for 7 nights

From

£444

A small dining area with a round glass table set for two and wicker chairs by two windows with ocean views at 6 The Beaches in Weymouth

6 The Beaches

Weymouth, Dorset

2 Guests
1 Beds
No pets
Wifi

for 7 nights

From

£456

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.

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