A curving country road flanked by dense green trees and grass.

Winder Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
$87 nightly
The price is $87
Nov 1 - Nov 2
Total with taxes and fees
High Dyke 1 - bed Studio Apartment nr Cockermouth
Luxury Bedroom

2. Luxury Loft Studio Apartment - Town Centre

Luxury Loft Studio Apartment - Town Centre
Whitehaven
10.0 out of 10, Exceptional, (3 reviews)
"Nice stay beautiful apartment in a lost part of the lakes"
United Kingdom
Martin J.
$145 nightly
The price is $145
Oct 9 - Oct 10
Total with taxes and fees
Luxury Loft Studio Apartment - Town Centre
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
$316 nightly
The price is $380
Nov 2 - Nov 3
Total with taxes and fees
High Wreah Bolt Hole
A beach with people walking and playing, a rocky area, and a grassy hill in the background.

4. 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
$287 nightly
The price is $287
Nov 2 - Nov 3
Total with taxes and fees
1 bedroom accommodation in St Bees, near Whitehaven
A beach with people walking and playing, a rocky area, and a grassy hill in the background.

5. 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
$283 nightly
The price is $283
Oct 12 - Oct 13
Total with taxes and fees
1 bedroom accommodation in St Bees, near Whitehaven
A beach with people walking and playing, a rocky area, and a grassy hill in the background.

6. 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
$308 nightly
The price is $308
Oct 6 - Oct 7
Total with taxes and fees
2 bedroom accommodation in St Bees, near Whitehaven
A rural setting with wooden cabins, gravel paths, and a clear sky.

7. 2 bedroom accommodation in Corney, near Millom

2 bedroom accommodation in Corney, near Millom
Corney, near Millom
10.0 out of 10, Exceptional, (2 reviews)
"absolutely beautiful up there! Will 100% be going back up there. staff were so kind&helpful if you needed anything. Cottages had basically everything you needed, very clean!"
United States
Lilli Maddocks
$222 nightly
The price is $222
Nov 2 - Nov 3
Total with taxes and fees
2 bedroom accommodation in Corney, near Millom
A stone building with a sloped roof, a gravel pathway, a wooden fence, and a grassy area with a gate.

8. 2 bedroom accommodation in Bassenthwaite, near Keswick

2 bedroom accommodation in Bassenthwaite, near Keswick
Bassenthwaite, near Keswick
9.6 out of 10, Exceptional, (7 reviews)
"Good, comfortable cottage in a great part of the Lakes."
United Kingdom
David P.
$393 nightly
The price is $393
Oct 29 - Oct 30
Total with taxes and fees
2 bedroom accommodation in Bassenthwaite, near Keswick
A stone building with a wooden door and a small patio area with two wicker chairs and a round table.

9. Stanger Cottage - a cottage that sleeps 4 guests in 2 bedrooms

Stanger Cottage - a cottage that sleeps 4 guests in 2 bedrooms
Braithwaite
8.8 out of 10, Excellent, (18 reviews)
"We had a wonderful stay in this cosy, quiet cottage with plenty of space and everything you needed. The beds were very comfortable, the kitchen well stocked but, you will need to bring any essentials salt and pepper, oil, etc. very nice pet welcome pack and packs of welcome with tea and cleaning items. There is a village shop nearby and several pub restaurants. There are a number of great walks on your doorstep from easy to more challenging without needing drive.. A beautiful area to explore so...
United Kingdom
Heather L.
$676 nightly
The price is $676
Oct 12 - Oct 13
Total with taxes and fees
Stanger Cottage - a cottage that sleeps 4 guests in 2 bedrooms
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, (37 reviews)
"Keswick Cottages has a range of high class properties in its portfolio. Being a smaller, local company they are able to provide excellent, personal service and support and have a detailed knowledge of the area. You cannot get this from larger agencies. Our stay at Lake View Cottage was very good. It was very clean, comfortable and well equipped and in an ideal yet quiet location for accessing all of the north Lake District and coast."
United States
Anonymous traveler
$1,531 nightly
The price is $1,531
Oct 25 - Oct 26
Total with taxes and fees
Lake View Cottage - an apartment that sleeps 4 guests in 2 bedrooms
A restaurant with wooden tables and chairs, a stone wall with logs, and a kitchen area.

11. Tawny Cottage - a cottage that sleeps 4 guests in 2 bedrooms

Tawny Cottage - a cottage that sleeps 4 guests in 2 bedrooms
Portinscale
9.8 out of 10, Exceptional, (26 reviews)
"Lovely cottage in a beautiful village with easy access into Keswick Town. Would definitely book again."
United States
Anonymous traveler
$669 nightly
The price is $669
Nov 2 - Nov 3
Total with taxes and fees
Tawny Cottage - a cottage that sleeps 4 guests in 2 bedrooms
A neatly made bed with a headboard, a mirror above it, and a fireplace below.

12. 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
$935 nightly
The price is $935
Nov 2 - Nov 3
Total with taxes and fees
Spa Cottage - a cottage that sleeps 3 guests in 2 bedrooms
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
$381 nightly
The price is $458
Oct 15 - Oct 16
Total with taxes and fees
Highlands Way Lodge
A cozy living room with a sofa, a coffee table, a fireplace, and a television on a cabinet.

14. Fell View - sleeps 4 guests in 2 bedrooms

Fell View - sleeps 4 guests in 2 bedrooms
Portinscale
9.8 out of 10, Exceptional, (28 reviews)
"Very comfortable and thoughtful accommodation, a lot of care had been taken with design. Location is convenient for accessing lots of walks. The Chalet and Lingholm are very good for lunch."
United States
Anonymous traveler
$823 nightly
The price is $823
Oct 12 - Oct 13
Total with taxes and fees
Fell View - sleeps 4 guests in 2 bedrooms
A conservatory with wicker furniture, a stone floor, and a view of a garden.

15. 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, (35 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.
$823 nightly
The price is $823
Oct 19 - Oct 20
Total with taxes and fees
Millside Cottage - a cottage that sleeps 4 guests in 2 bedrooms
A lush landscape with a variety of trees and a grassy area.

16. 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, (42 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
$736 nightly
The price is $736
Oct 8 - Oct 9
Total with taxes and fees
Roslin - a cottage that sleeps 4 guests in 2 bedrooms
Indulge and unwind in a hot tub - available to hire

17. Brandlehow - a house that sleeps 7 guests in 4 bedrooms

Brandlehow - a house that sleeps 7 guests in 4 bedrooms
Portinscale
8.8 out of 10, Excellent, (23 reviews)
"Our 3rd visit to Brandlehow and another truly stunning week, a mix of activity and relaxation. The house, the location, and the Keswick Cottages team all combine to make a fantastic experience … plus meeting our late changes to suit the wedding vows renewal at Gretna midweek. It made it all so very special for all of us, thank you"
United States
Richard H.
$1,757 nightly
The price is $1,757
Oct 5 - Oct 6
Total with taxes and fees
Brandlehow - a house that sleeps 7 guests in 4 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)
"Rosebank is a very clean, comfortable cottage. Lovely views across to the hills at the back & pheasants & lots of birds visit the garden.Very handy for the Coledale Inn, & the Royal Oak & 5 minutes in the car to Keswick if you want to try something different like Thai food at the the Star of Siam. We have stayed there frequently & will definitely go again. Many thanks."
United States
Brenda G.
$1,187 nightly
The price is $1,187
Nov 2 - Nov 3
Total with taxes and fees
Rose Bank Cottage - a cottage that sleeps 5 guests in 3 bedrooms
A compact kitchen with a gas stove, oven, and a microwave. There is a window providing natural light and a view of the outside.

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

Abacourt Cottage - a cottage that sleeps 5 guests in 3 bedrooms
Central Keswick
9.4 out of 10, Exceptional, (16 reviews)
"Great location "
United Kingdom
Gary B.
$861 nightly
The price is $861
Oct 19 - Oct 20
Total with taxes and fees
Abacourt Cottage - a cottage that sleeps 5 guests in 3 bedrooms
A sunlit room with a large window, a plush armchair, a heart-shaped decoration, and a dining area in the background.

20. Fern Cottage - a house that sleeps up to 7 guests in 4 bedrooms

Fern Cottage - a house that sleeps up to 7 guests in 4 bedrooms
Portinscale
10.0 out of 10, Exceptional, (12 reviews)
"A great location and very homely comfortable and well equipped cottage. ."
United States
Andrew T.
$851 nightly
The price is $851
Oct 4 - Oct 5
Total with taxes and fees
Fern Cottage - a house that sleeps up to 7 guests in 4 bedrooms
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

Lake District Castle Inn hotel & Spa

Lake District Castle Inn hotel & Spa

8/10 Good
"The property is in a nice quiet area with plenty of parking. There is also a bus stop right outside. Our room was great with a great view of the valley. I think the stay is good for a relaxing evening with lots to do in the property and around. They have some vegetarian options in the menu as well. They have spa treatments that are advertised for 7 days a week, but don’t seem to operate on Sundays or Mondays, which is bad if you’re planning to spend the weekend there. Not the property if you were planning to get a massage after a long hike. As it is a period property, there are no lifts to the rooms, so you may need to carry your luggage up the stairs through a maze of doors although I think it’s only one floor so should generally be okay.."
Ayush 3-night trip
Posted 2 days ago
Lake District Castle Inn hotel & Spa

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 $287 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.

Explore a world of travel with Expedia

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.