Rolling hills, a field, and scattered trees.

Winsham Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Winsham vacation rentals

A cozy living room with a fireplace, wooden furniture, and a decorative vase.

1. Church Farmhouse

Church Farmhouse
3.0 star property
Chard
The price is CA $977
CA $1,173 total
includes taxes & fees
Sep 16 - Sep 17
Church Farmhouse
A spacious living area with a kitchen, a dining table, and a comfortable seating arrangement.

2. Ammerham Farm Cottage

Ammerham Farm Cottage
3.0 star property
Chard
The price is CA $938
CA $1,125 total
includes taxes & fees
Sep 26 - Sep 27
Ammerham Farm Cottage

3. Briar Orchard Annex

Briar Orchard Annex
2.0 star property
Chard
The price is CA $919
CA $1,102 total
includes taxes & fees
Sep 26 - Sep 27
Briar Orchard Annex
A silver trailer-like structure in a rural setting with a view of houses and a body of water in the background.

4. Rare Mini Airstream style Clipper in the The Jurassic Coast with optional Hot Tub & Sauna

Rare Mini Airstream style Clipper in the The Jurassic Coast with optional Hot Tub & Sauna
Devon
The price is CA $158
CA $233 total
includes taxes & fees
Sep 14 - Sep 15
Rare Mini Airstream style Clipper in the The Jurassic Coast with optional Hot Tub & Sauna
A modern kitchen with a wooden table, two chairs, a sink, and a window with a view of greenery.

5. Woodstock Retreat

Woodstock Retreat
3.5 star property
Axminster
10.0 out of 10, Exceptional, (2 reviews)
"A very nice property in a quiet location. Ideal for a complete getaway, with plenty of interesting places to visit not far away. Debbie is a lovely host, very welcoming and helpful. Would definitely recommend Woodstock Retreat. "
United Kingdom
Paul
The price is CA $443
CA $531 total
includes taxes & fees
Sep 18 - Sep 19
Woodstock Retreat
A two-story house with a sloped roof, large windows, and a patio area with outdoor furniture.

6. Cosy cottage for Autumn breaks

Cosy cottage for Autumn breaks
Morcombelake
9.6 out of 10, Exceptional, (7 reviews)
"Great place to stay, "
United Kingdom
Gary C.
The price is CA $261
CA $414 total
includes taxes & fees
Sep 14 - Sep 15
Cosy cottage for Autumn breaks
A two-story house with a sloped roof, a front porch with chairs, and a small garden area.

7. Cosy country cottage for couples

Cosy country cottage for couples
BRIDPORT
9.4 out of 10, Exceptional, (6 reviews)
"We had a great stay ...house was lovely, well equipped & communication was very good with owner."
United Kingdom
Tracey H.
The price is CA $280
CA $435 total
includes taxes & fees
Sep 16 - Sep 17
Cosy country cottage for couples
A stone house with a thatched-roof extension, a stone well, and a grassy yard.

8. The Apple House at Moorbath Farm

The Apple House at Moorbath Farm
Bridport
10.0 out of 10, Exceptional, (5 reviews)
"Really nice property ,all nicely finished to a high standard.liked the oak used. We had a nice few days-if you want somewhere peaceful and quiet this is ideal. "
United Kingdom
christopher b.
The price is CA $242
CA $382 total
includes taxes & fees
Sep 27 - Sep 28
The Apple House at Moorbath Farm
A brick house with a sloped roof, a patio with a table and chairs, and a garden with various plants.

9. Battys Barn at Moorbath Farm

Battys Barn at Moorbath Farm
Bridport
10.0 out of 10, Exceptional, (7 reviews)
"Host was very helpful with good communication. The property was very well presented and very clean. It was a really nice stay."
United Kingdom
James A.
The price is CA $381
CA $521 total
includes taxes & fees
Sep 13 - Sep 14
Battys Barn at Moorbath Farm
An outdoor patio with wicker furniture, a grill with food, and a stone building in the background.

10. Withy Cottages

Withy Cottages
3.5 star property
Langport
9.6 out of 10, Exceptional, (45 reviews)
"Lovely quaint cottage ideal for a rural stay."
United Kingdom
James
The price is CA $272
CA $326 total
includes taxes & fees
Sep 10 - Sep 11
Withy Cottages
A vintage trailer with a hot tub and wooden deck, surrounded by a grassy field.

11. Vintage 1950 Airstream with valley views, fire pit and stargazing

Vintage 1950 Airstream with valley views, fire pit and stargazing
Devon
10.0 out of 10, Exceptional, (1 review)
"Fantastic stay , will definitely be coming back , the owner couldn’t help enough, great stay"
United States
John B.
The price is CA $177
CA $261 total
includes taxes & fees
Sep 10 - Sep 11
Vintage 1950 Airstream with valley views, fire pit and stargazing
A tent with a central bed, two lanterns, and a fireplace.

12. Bell Tent Sleeps 4 with Woodburner & Sauna · Blackdown Hills

Bell Tent Sleeps 4 with Woodburner & Sauna · Blackdown Hills
Devon
The price is CA $233
CA $308 total
includes taxes & fees
Sep 10 - Sep 11
Bell Tent Sleeps 4 with Woodburner & Sauna · Blackdown Hills
A room with a large window overlooking a beach and cliffs.

13. Private off-grid vintage Airstream hideaway for Jurassic Coast adventures and stargazing nights

Private off-grid vintage Airstream hideaway for Jurassic Coast adventures and stargazing nights
Devon
The price is CA $205
CA $298 total
includes taxes & fees
Sep 10 - Sep 11
Private off-grid vintage Airstream hideaway for Jurassic Coast adventures and stargazing nights
A small, single-story house with a stone wall and a wooden deck, surrounded by lush greenery and a stone pathway.

14. 1 bedroom accommodation in Uplyme, near Lyme Regis

1 bedroom accommodation in Uplyme, near Lyme Regis
Uplyme, near Lyme Regis
10.0 out of 10, Exceptional, (35 reviews)
"The Lodge is beautifully clean , well equipped and with access to a lovely garden and views of all the inquisitive wildlife .. We enjoyed the walk along the River Lim to Lyme Regis and onwards to a walk along the coastal path and back to Uplyme. There isn't much in Uplyme , but Lyme Regis is close , especially by car , where we found very good restaurants . We had a fabulous weekend break and would highly recommend the Lodge."
United States
Sara Todd
The price is CA $565
CA $565 total
includes taxes & fees
Oct 9 - Oct 10
1 bedroom accommodation in Uplyme, near Lyme Regis
A conservatory with wicker furniture, a glass table, and a red vase.

15. Downside

Downside
3.5 star property
Crewkerne
10.0 out of 10, Exceptional, (1 review)
"Good value for money option"
Greece
Theodoros
The price is CA $481
CA $577 total
includes taxes & fees
Sep 26 - Sep 27
Downside
A row of colorful beach huts with numbered doors, each featuring a small window and a door handle.

16. Holiday Cottage with seafront beach hut - sleeps 4

Holiday Cottage with seafront beach hut - sleeps 4
Lyme Regis
9.4 out of 10, Exceptional, (121 reviews)
"Great central location."
United Kingdom
Shane H.
The price is CA $308
CA $347 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Cottage with seafront beach hut - sleeps 4
A cozy living room with a stone fireplace, a patterned rug, a leather sofa with colorful cushions, and a stone wall.

17. Set in the heart of Lyme Regis in the conservation area of the old town

Set in the heart of Lyme Regis in the conservation area of the old town
Lyme Regis
9.8 out of 10, Exceptional, (27 reviews)
"Drakes cottage is in the centre of Lyme Regis, perfect. It also has a parking place, which is very useful. Lovely bedrooms and bathrooms."
United States
Kathryn R.
The price is CA $454
CA $519 total
includes taxes & fees
Sep 24 - Sep 25
Set in the heart of Lyme Regis in the conservation area of the old town
A dining area with a wooden table, chairs, and a sofa. There is a chandelier above the table and a window with a view of the outdoors.

18. Cosy yet spacious cottage in heart of East Devon near Jurassic Coast

Cosy yet spacious cottage in heart of East Devon near Jurassic Coast
Ottery Saint Mary
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful property lovely host"
United Kingdom
Jane
The price is CA $252
CA $364 total
includes taxes & fees
Sep 11 - Sep 12
Cosy yet spacious cottage in heart of East Devon near Jurassic Coast
A cozy living room with a fireplace, leather sofas, a wooden coffee table, and a TV mounted on the wall.

19. Cozy Gnome Cottage Annex Near Sidmouth

Cozy Gnome Cottage Annex Near Sidmouth
3.5 star property
Ottery St Mary
9.8 out of 10, Exceptional, (7 reviews)
"It was very well equipped and comfortable beds."
United Kingdom
JV
The price is CA $295
CA $295 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Gnome Cottage Annex Near Sidmouth
A modern living room with a sofa, coffee table, and a kitchen area with a washing machine.

20. Streamside Apartments

Streamside Apartments
3.5 star property
Yeovil
10.0 out of 10, Exceptional, (37 reviews)
"Excellent accommodation!"
Norway
Anonymous traveller
The price is CA $205
CA $205 total
includes taxes & fees
Oct 6 - Oct 7
Streamside Apartments
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

TheHillbrookSherborne

TheHillbrookSherborne

10/10 Excellent
"Great location and large clean and comfortable room"
Stephen 1-night trip
Posted 2 hours ago
TheHillbrookSherborne

Find out more about Winsham

Everything you need to know about Winsham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winsham vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Winsham vacation 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winsham vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winsham vacation rentals we have selected for you start as low as CA $326 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winsham rentals

At Expedia, we put the best Winsham vacation 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 vacation.

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 vacation rentals in Winsham?

Yes, we give you a choice of vacation rentals close to the most popular sights in Winsham, or you can select a more secluded option if you're looking for relaxation.

What's the top vacation rental that Winsham has to offer?

Holiday Home of the Year | Sleeps 20 | Tennis, Gardens | 1m Jurassic Coast Beach: This vacation home rental near Winsham is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 9 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself 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 National Landscape. In the larger area, you’ll find Barrington Court and Charmouth Heritage Coast Centre.

What are vacation rentals like in Winsham?

Vacation rentals are private properties you can book for several days or more in Winsham. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family trip.