Winsham Holiday Rentals

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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Holiday Rentals in Winsham

A charming character cottage with Abbey view
Outdoor dining

A charming character cottage with Abbey view

10.0 out of 10, Exceptional, (143)
"Bensly Cottage is a wonderfully cosy and characterful place to stay that is within easy walking distance for everything in Sherborne including the castles (and only a couple of minutes walk from the abbey). It makes it an ideal place to stay if you want to explore Sherborne on foot. We thoroughly enjoyed our stay! "
A charming character cottage with Abbey view
Withy Cottages
Superior Villa, Private Bathroom (Withy House) | Miscellaneous

Withy Cottages

3.5 star property
9.6 out of 10, Exceptional, (43)
"Lovely quaint cottage ideal for a rural stay."
The price is AU$303
includes taxes & fees
5 Oct - 6 Oct
Withy Cottages
Spacious Converted Barn on a Flower Farm, Devon Countryside, Family Friendly
Dining

Spacious Converted Barn on a Flower Farm, Devon Countryside, Family Friendly

9.8 out of 10, Exceptional, (38)
"We had a lovely week’s stay as three families. The house is great, lovely location for walks and bike rides, and easy to get to other places across Devon. "
Spacious Converted Barn on a Flower Farm, Devon Countryside, Family Friendly
Dragonfly
Cottage | Interior

Dragonfly

3.0 star property
Dragonfly
10 Bay View Court
Beach nearby

10 Bay View Court

3.0 star property
10.0 out of 10, Exceptional, (1)
"The bottom lock on the front door is too stiff. One side of the double bed is broken. There is no mention of the parking permit and car park on the agents website. "
The price is AU$872
includes taxes & fees
7 Oct - 8 Oct
10 Bay View Court
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
Exterior detail

Self Contained Garden Studio With Private Decked Terrace, close to town and sea

9.6 out of 10, Exceptional, (143)
"Very pleasant stay; will pass on info to other family members for when they visit Bridport. "
Self Contained Garden Studio With Private Decked Terrace, close to town and sea
BUTTERCUP COTTAGE in beautiful Devon countryside.
Sun-loungers

BUTTERCUP COTTAGE in beautiful Devon countryside.

9.8 out of 10, Exceptional, (86)
"Everything was excellent from Day 1 Accommodation had everything one needs and a fabulous welcome pack! Host was around and ensured we had good local knowledge. Definitely recommend!"
BUTTERCUP COTTAGE in beautiful Devon countryside.
Cosy Somerset cottage, open fire, country walks, pet friendly.
Exterior detail

Cosy Somerset cottage, open fire, country walks, pet friendly.

9.8 out of 10, Exceptional, (59)
"Lovely place to stay in Somerset. Spacious and quiet."
Cosy Somerset cottage, open fire, country walks, pet friendly.
Edwardian country house on Dorset's Jurassic coast
Beach nearby, sun-loungers

Edwardian country house on Dorset's Jurassic coast

10.0 out of 10, Exceptional, (30)
"This house is perfect for large groups, with space to comfortably sleep everyone and lots of communal space, both inside and out. The grounds are lovely with beautiful views out over the countryside. Its location, is perfect for visiting Lyme Regis, we spent a great day by the sea. "
Edwardian country house on Dorset's Jurassic coast
Beautiful thatched country cottage, quiet countryside position .
Outdoor dining

Beautiful thatched country cottage, quiet countryside position .

9.8 out of 10, Exceptional, (68)
"The cottage was great, small but just what we needed and great to be near the coast but have our own quiet, cosy space to come back to. "
Beautiful thatched country cottage, quiet countryside position .
DAISY COTTAGE in peaceful rural location
Sun-loungers

DAISY COTTAGE in peaceful rural location

9.6 out of 10, Exceptional, (100)
"Cozy cottage, beautiful landscape, invites you to relax. We'll be back."
DAISY COTTAGE in peaceful rural location
Fabulous river and coastal views. Seaton beach 5 min drive, Lyme Regis 10 mins.
Marina

Fabulous river and coastal views. Seaton beach 5 min drive, Lyme Regis 10 mins.

9.8 out of 10, Exceptional, (38)
"A beautiful property in the perfect location, close to Lyme Regis, Beer and many more. The house was lovely, so comfortable with a view to die for. We will be back! Thanks so much Stephanie for a wonderful week! "
Fabulous river and coastal views. Seaton beach 5 min drive, Lyme Regis 10 mins.
Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town
Beach nearby

Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town

10.0 out of 10, Exceptional, (57)
"Quiet, peaceful location with amenities close to hand just the place for a relaxing week. Property is very well equipped and the secluded garden at the back a bonus."
Luxury cottage, 15 minutes to beach, stunning garden views, two min walk to town
Homeland
Fridge, dishwasher, electric kettle, toaster

Homeland

3.0 star property
The price is AU$2,470
includes taxes & fees
26 Oct - 27 Oct
Homeland
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom
Outdoor spa tub

The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom

9.6 out of 10, Exceptional, (44)
"A lovely relaxed stay, nice peaceful area, plenty of places to walk, highly recommend gor a bit of r&r."
The Old Coach House in Dorset's Area of Outstanding Beauty - 1 bedroom
52 Fernhill Heights
Living room

52 Fernhill Heights

3.5 star property
6.0 out of 10, (2)
"What an amazing place to stay! Close to many activities but at the same time a lovely quiet location. Very well equipped with lots of DVD choices, board games and everything you need to maintain your stay. The beds and bedding was my highlight one of the most comfortable beds I’ve slept in for years! Will definitely be back, thanks for having us."
The price is AU$811
includes taxes & fees
11 Oct - 12 Oct
52 Fernhill Heights
Period apartment set in Grade 2 listed building
Marina

Period apartment set in Grade 2 listed building

Period apartment set in Grade 2 listed building
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
Fridge, microwave, oven, stovetop

Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly

9.6 out of 10, Exceptional, (21)
"Ten friends and family enjoyed a long weekend in this very pretty location. Lots to see and do near by but we also made great use of the garden and pool room."
Large, cosy Self Catering Cottage Set In Beautiful Countryside. Pet friendly
A wonderful Grade II listed cottage in stunning countryside with private beach
Exterior

A wonderful Grade II listed cottage in stunning countryside with private beach

10.0 out of 10, Exceptional, (4)
"We have had a great weekend stay for our family. Perfect in every way for what we required. Although the beech path was closed - which was a shame. "
A wonderful Grade II listed cottage in stunning countryside with private beach
Half Pint Cottage
Fridge, dishwasher, electric kettle, toaster

Half Pint Cottage

3.0 star property
10.0 out of 10, Exceptional, (1)
"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."
The price is AU$858
includes taxes & fees
7 Oct - 8 Oct
Half Pint Cottage
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 Winsham Hotel Reviews

The Great Western Hotel

The Great Western Hotel

10/10 Excellent
"Lovely hotel with beautiful rooms. Very interesting history. Handy for town , 5 mins walk, hundreds of different restaurants Lovely to have decent tea and coffee facilities in our room, with delicious biscuits. A really pleasant little hotel, very handy for the Station – just opposite. Staff are extremely friendly "
Julia 1-night trip
Posted 3 days ago
The Great Western Hotel

Find out more about Winsham

Find out more about Winsham

Everything you need to know about Winsham 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 Winsham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, 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 Winsham holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winsham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winsham. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winsham 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 Winsham holiday rentals we have selected for you start as low as AU$303 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winsham rentals

At Expedia, we put the best Winsham 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 Winsham 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 Winsham 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 Winsham. 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 holiday rentals in Winsham?

Yes, there are holiday rentals close to the most popular sights in Winsham, 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 Winsham has to offer?

Spacious Converted Barn on a Flower Farm, Devon Countryside, Family Friendly: This holiday home rental outside of Winsham offers a fireplace, a balcony and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What can I see and do in Winsham?

While exploring the area, visit family-friendly sights like Lyme Regis Marine Aquarium, or get outside and enjoy nature at Dorset Area of Outstanding Natural Beauty. In the wider area, you’ll find Barrington Court and Charmouth Heritage Coast Centre.

What are holiday rentals like in Winsham?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winsham. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for a small group gathering.