Winder Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Winder vacation rentals

A rustic stone wall with a wooden table and two blue chairs.

1. High Dyke 1 - bed Studio Apartment nr Cockermouth

High Dyke 1 - bed Studio Apartment nr Cockermouth
3.0 star property
Cockermouth
8.4 out of 10, Very good, (6 reviews)
"A really lovely place to stay! The studio is lovely, a really comfortable space and very clean and in a lovely location. We were greeted by Lee a lovely guy and happy to help with any questions we had. We would happily stay there again! "
United Kingdom
Paul
$91 nightly
The price is $91
Nov 15 - Nov 16
Total with taxes and fees
High Dyke 1 - bed Studio Apartment nr Cockermouth
A beach with people walking and playing, a rocky area, and a grassy hill in the background.

2. 1 bedroom accommodation in St Bees, near Whitehaven

1 bedroom accommodation in St Bees, near Whitehaven
St Bees, near Whitehaven
10.0 out of 10, Exceptional, (11 reviews)
"Good base for accessing Lake District."
United States
Neal Ferrie
$273 nightly
The price is $273
Nov 7 - Nov 8
Total with taxes and fees
1 bedroom accommodation in St Bees, near Whitehaven
A living room with a wooden coffee table, a TV, a black door, and a kitchen in the background.

3. High Wreah Bolt Hole

High Wreah Bolt Hole
2.0 star property
Whitehaven
10.0 out of 10, Exceptional, (2 reviews)
"Lovely unique little property ideal for a relaxing getaway. Thoroughly enjoyed my time there and can see me returning."
United Kingdom
Dean
$354 nightly
The price is $425
Nov 21 - Nov 22
Total with taxes and fees
High Wreah Bolt Hole
A coastal marina with boats, a crane, and a grassy area with a bench.

4. 2 bedroom accommodation in Ritson Wharf, near Cockermouth

2 bedroom accommodation in Ritson Wharf, near Cockermouth
Ritson Wharf, near Cockermouth
10.0 out of 10, Exceptional, (8 reviews)
"Absolutely fabulous place to stay.Everything provided by very friendly hostsGreat area to explore"
United States
PETER WILKINSON
$238 nightly
The price is $238
Nov 26 - Nov 27
Total with taxes and fees
2 bedroom accommodation in Ritson Wharf, near Cockermouth
A beach with people walking and playing, a rocky area, and a grassy hill in the background.

5. 2 bedroom accommodation in St Bees, near Whitehaven

2 bedroom accommodation in St Bees, near Whitehaven
St Bees, near Whitehaven
10.0 out of 10, Exceptional, (6 reviews)
"We enjoyed our stay immensely. The owner was very attentive to our needs, property was very cosy and warm, and ideally located for local amenities and touring the area. We will return!"
United States
Steven Harrison
$246 nightly
The price is $246
Nov 7 - Nov 8
Total with taxes and fees
2 bedroom accommodation in St Bees, near Whitehaven
A modern living room with a sofa, a coffee table, a dining area with a table and chairs, and a lamp.

6. Cosy Keswick 1BR Sleeps 2 by Stay With Us

Cosy Keswick 1BR Sleeps 2 by Stay With Us
2.0 star property
Keswick
$291 nightly
The price is $349
Nov 22 - Nov 23
Total with taxes and fees
Cosy Keswick 1BR Sleeps 2 by Stay With Us
A coastal road with a sea view, a red stop sign, and a grassy embankment.

7. 1 bedroom accommodation in St Bees, near Whitehaven

1 bedroom accommodation in St Bees, near Whitehaven
St Bees, near Whitehaven
10.0 out of 10, Exceptional, (10 reviews)
"Lovely stay in a nice quiet little town"
United States
Dan Smith
$273 nightly
The price is $273
Nov 13 - Nov 14
Total with taxes and fees
1 bedroom accommodation in St Bees, near Whitehaven
A modern kitchen with white cabinets, a built-in oven, a microwave, and a window with a view of the outside.

8. 1 bedroom accommodation in Keswick

1 bedroom accommodation in Keswick
Keswick
9.8 out of 10, Exceptional, (19 reviews)
"Lovely appartment and great location.A bonus having allocated parking.The only reason i didnt give a 5* is due to the bathroom tap was really difficult to turn on and off when running cold water and both the bath and sink slow to drain."
United States
Linda Bonner
$373 nightly
The price is $373
Nov 21 - Nov 22
Total with taxes and fees
1 bedroom accommodation in Keswick
A modern living room with a dark brown leather sofa, a dining table with four chairs, and a large flat-screen TV on a wooden stand.

9. Carlton 2

Carlton 2
3.5 star property
Keswick
10.0 out of 10, Exceptional, (8 reviews)
"The room was lovely, it was very central for all the amenities, it was handy having a car parking free space ,everything was spotless we will definitely be back."
United Kingdom
Gladys
$295 nightly
The price is $295
Dec 3 - Dec 4
Total with taxes and fees
Carlton 2
A white building with a sloped roof, surrounded by a well-maintained lawn and a gravel path leading to the entrance.

10. Lake View Cottage - an apartment that sleeps 4 guests in 2 bedrooms

Lake View Cottage - an apartment that sleeps 4 guests in 2 bedrooms
Thornthwaite
9.8 out of 10, Exceptional, (38 reviews)
"We had a wonderful stay at Lake View Cottage. The cottage was clean, comfortable and well maintained, with a fantastic location for exploring the area. We thoroughly enjoyed our visit and would happily stay here again when we next visit the Lake District."
United States
Ivan K.
$545 nightly
The price is $545
Nov 23 - Nov 24
Total with taxes and fees
Lake View Cottage - an apartment that sleeps 4 guests in 2 bedrooms
A wooden cabin with a dining area, a television mounted on the wall, and a view of the outside.

11. 1 bedroom accommodation in Corney, near Millom

1 bedroom accommodation in Corney, near Millom
Corney, near Millom
10.0 out of 10, Exceptional, (1 review)
"if you like peace and quiet this place is for you"
United States
Tomasz Dec
$198 nightly
The price is $198
Nov 9 - Nov 10
Total with taxes and fees
1 bedroom accommodation in Corney, near Millom
A building labeled "Chaucer Lodge" with a sign indicating "PRIVATE Parking Only."

12. Short breaks available all year.

Short breaks available all year.
Keswick
9.0 out of 10, Wonderful, (18 reviews)
"Had a great holiday. Even the weather was good!"
United States
Jane Richards
$273 nightly
The price is $273
Dec 6 - Dec 7
Total with taxes and fees
Short breaks available all year.
A living room with a fireplace, a sofa, a large window with a view of houses, and a television on a shelf.

13. Highlands Way Lodge

Highlands Way Lodge
3.0 star property
Workington
10.0 out of 10, Exceptional, (1 review)
"Wonderful cabin in a great location. Super clean and pristine when we arrived. Highly recommend and definitely booking with this host/cabin again 👍"
United Kingdom
Rebecca
$455 nightly
The price is $546
Nov 13 - Nov 14
Total with taxes and fees
Highlands Way Lodge
A spacious living area with a staircase, a dining table, a sofa, and a television.

14. Glen Cottage - sleeps 4 guests in 2 bedrooms

Glen Cottage - sleeps 4 guests in 2 bedrooms
Braithwaite
9.8 out of 10, Exceptional, (36 reviews)
"We had a lovely stay here, perfect location for walks, pubs/restaurants, Keswick town. The cottage had everything we needed and more, loved the garden for our dog and very comfy bed."
United States
Michelle E.
$482 nightly
The price is $482
Nov 8 - Nov 9
Total with taxes and fees
Glen Cottage - sleeps 4 guests in 2 bedrooms
A neatly made bed with a headboard, a mirror above it, and a fireplace below.

15. Spa Cottage - a cottage that sleeps 3 guests in 2 bedrooms

Spa Cottage - a cottage that sleeps 3 guests in 2 bedrooms
Braithwaite
9.8 out of 10, Exceptional, (84 reviews)
"This was our third visit to Spa Cottages. It is a great base for exploring the Lake District. Parking can be a bit tight, but for the majority of the time we were able to park directly outside the property."
United States
Anonymous traveler
$476 nightly
The price is $476
Nov 9 - Nov 10
Total with taxes and fees
Spa Cottage - a cottage that sleeps 3 guests in 2 bedrooms
A conservatory with wicker furniture, a stone floor, and a view of a garden.

16. Millside Cottage - a cottage that sleeps 4 guests in 2 bedrooms

Millside Cottage - a cottage that sleeps 4 guests in 2 bedrooms
Braithwaite
9.6 out of 10, Exceptional, (36 reviews)
"Beautiful cottage, very well equipped in fantastic location with parking. Could not have asked for more! Will definitely be back!"
United States
Gillian M.
$484 nightly
The price is $484
Nov 8 - Nov 9
Total with taxes and fees
Millside Cottage - a cottage that sleeps 4 guests in 2 bedrooms
A room with a view of mountains through a window, a green armchair with a pillow, and a small table with a vase.

17. Roslin - a cottage that sleeps 4 guests in 2 bedrooms

Roslin - a cottage that sleeps 4 guests in 2 bedrooms
Portinscale
9.4 out of 10, Exceptional, (44 reviews)
"Great accommodation in a lovely little village with fantastic views. Everything you could need to make this a home from home and only a 20 minute walk into Keswick."
United States
Anonymous traveler
$538 nightly
The price is $538
Nov 16 - Nov 17
Total with taxes and fees
Roslin - a cottage that sleeps 4 guests in 2 bedrooms
A traditional two-story house with a stone pathway leading to the entrance.

18. Rose Bank Cottage - a cottage that sleeps 5 guests in 3 bedrooms

Rose Bank Cottage - a cottage that sleeps 5 guests in 3 bedrooms
Braithwaite
9.6 out of 10, Exceptional, (40 reviews)
"Plenty of room for 4 adults & an excited Springer spaniel. Great to have a dog friendly garden - not always the case when advertised as such! Lots of walks from the doorstep. Local shop sells delicious cakes to take on walks!"
United States
Anonymous traveler
Rose Bank Cottage - a cottage that sleeps 5 guests in 3 bedrooms
A bedroom with a bed, bedside tables, a chair, a window, and a skylight.

19. Barf Cottage - a cottage that sleeps 5 guests in 3 bedrooms

Barf Cottage - a cottage that sleeps 5 guests in 3 bedrooms
Portinscale
9.6 out of 10, Exceptional, (38 reviews)
"Really nice characterful cottage in a great location for hiking from the door with parking for two cars. Easy access to Braithwaite and the facilities and walks from there , and also to Keswick town centre. Would benefit from a more extensive ‘welcome pack’ and other basics you often get in cottages these days ( fresh milk , kitchen roll , oils and condiments etc ) but overall would definitely recommend the cottage ."
United States
Ian R.
$578 nightly
The price is $578
Nov 16 - Nov 17
Total with taxes and fees
Barf Cottage - a cottage that sleeps 5 guests in 3 bedrooms
Keswick | Cumbria, England

20. Flat 2 Lonsdale House

Flat 2 Lonsdale House
Keswick
10.0 out of 10, Exceptional, (16 reviews)
"Stayed here for two nights, the property is superb. Spotless clean and in a brilliant location. Will definitely return, and 100% recommend."
United Kingdom
Stephen C.
$354 nightly
The price is $354
Nov 29 - Nov 30
Total with taxes and fees
Flat 2 Lonsdale House
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 Winder Hotel Reviews

A spacious restaurant with a high ceiling and large windows, featuring wooden flooring and modern furniture.
The Melbreak Hotel

The Melbreak Hotel

The Melbreak Hotel
Workington

10/10 Excellent

It was all good.
United States
James
Reviewed September 7, 2025
The Melbreak Hotel

Find out more about Winder

Everything you need to know about Winder 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 Winder vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Winder vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winder vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winder. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winder in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $91 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winder rentals

At Expedia, we put the best Winder 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 Winder 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 Winder 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 Winder. 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 a vacation rental in Winder?

Yes, we offer vacation rentals near the most popular attractions in Winder, or you can choose a more secluded option if you're looking for a relaxing stay. Winder is known for its parks.

What are some of the best vacation home rentals in Winder?

Lovely mews cottage in the western Lake District: This vacation home rental outside of Winder is equipped with a garden, laundry facilities, and WiFi to help you feel comfortable during your stay.

What can I see and do in Winder?

Explore the area and family-friendly sights such as Rowrah Circuit, or get out into nature at a spot like St. Bees Beach. Frizington Library and Crummock Water are a couple of places you'll find in the larger area.

What are vacation rentals like in Winder?

Vacation rentals are privately owned properties you can book for several days or longer in Winder. Vacation rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you to travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for small groups.

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