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Castleton Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Castleton vacation rentals

Dishwasher, highchair
2 bedroom accommodation in Castleton near Whitby

Cottage in Castleton near Whitby

2 bedroom accommodation in Castleton near Whitby
10.0 out of 10, Exceptional, (1)
"We had a fantastic 10-day stay in this wonderful cottage. Sara and Jason welcomed us with a great welcome package and a heated cottage. The house is well furnitured, and many details make the stay very comfortable. Hope to come back soon. "
Germany
Sonja F.
$386 nightly
The price is $386
Jan 4 - Jan 5, 2026
Total with taxes and fees
2 bedroom accommodation in Castleton near Whitby
Bar (on property)
Station Suites

Aparthotel in Middlesbrough

Station Suites
4.0 star property
9.6 out of 10, Exceptional, (19)
"My stay was beautiful,clean environment"
United Kingdom
Yemi
$91 nightly
The price is $109
Dec 27 - Dec 28
Total with taxes and fees
Station Suites
Cottage | Interior
Weavers Cottage

Cottage in Middlesbrough

Weavers Cottage
3.5 star property
$1,047 nightly
The price is $1,257
Jan 8 - Jan 9, 2026
Total with taxes and fees
Weavers Cottage
Smart TV
Entire house 🏠. suitable for families and workers.

Vacation Home in Middlesbrough

Entire house 🏠. suitable for families and workers.
10.0 out of 10, Exceptional, (2)
"Very clean and a good area"
United Kingdom
Marek
$170 nightly
The price is $170
Dec 29 - Dec 30
Total with taxes and fees
Entire house 🏠. suitable for families and workers.
Studio | Dining
Welbury Studio Retreat

Apartment in Northallerton

Welbury Studio Retreat
3.0 star property
9.0 out of 10, Wonderful, (2)
"Very helpful, we were going to be later than anticipated arriving, phoned to let them know, they reassured us it was no problem, everything was ready for our stay. Check-in at the bar was easy, staff showed us to our studio, staff very cheerful. Food in the pub was great, not just pub grub. Only downside, studio was small."
United Kingdom
Gillian
$87 nightly
The price is $105
Jan 1 - Jan 2, 2026
Total with taxes and fees
Welbury Studio Retreat
Superior Cottage, 2 Bedrooms (Mustard) | Iron/ironing board, free WiFi, bed sheets
Craven Garth Cottages

Cottage in Pickering

Craven Garth Cottages
3.0 star property
9.4 out of 10, Exceptional, (46)
"Really nice place,friendly landlord and very helpful"
United Kingdom
Corin
$251 nightly
The price is $302
Jan 10 - Jan 11, 2026
Total with taxes and fees
Craven Garth Cottages
Fridge, microwave, oven, stovetop
Stoney Nook Cottage

Cottage in Guisborough

Stoney Nook Cottage
9.2 out of 10, Wonderful, (5)
"Beautifully renovated cottage with comfortable bed and modern washroom. Conveniently located for exploring Guisborough and helpful guidebook with suggestions for the kids and adults. The grocery store is a 5-minute block away also. Andy was very helpful and easy to communicate with."
Canada
Shelley & J.
$130 nightly
The price is $130
Jan 18 - Jan 19, 2026
Total with taxes and fees
Stoney Nook Cottage
Premium Apartment, Private Bathroom, Marina View (3 -Bedroom Lux Apartment) | Lounge
Whitby Bridge Luxury Apartments

Apartment in Whitby

Whitby Bridge Luxury Apartments
3.5 star property
7.8 out of 10, Good, (17)
"Very close to Whitby swing bridge so handy for attractions, restaurants, coop 3 minute walk if want self catering. Newly renovated, very clean, lovely views."
United Kingdom
Susan
$152 nightly
The price is $174
Jan 4 - Jan 5, 2026
Total with taxes and fees
Whitby Bridge Luxury Apartments
2 bedrooms, free WiFi, bed sheets
Keldholme Cottage 1 - UK10992

Cottage in Keldholme, near Kirkbymoorside

Keldholme Cottage 1 - UK10992
9.8 out of 10, Exceptional, (7)
"Excellent for get away from it all beautiful countryside and walks."
United States
John Kelly
$353 nightly
The price is $353
Jan 2 - Jan 3, 2026
Total with taxes and fees
Keldholme Cottage 1 - UK10992
1 bedroom, iron/ironing board, travel crib, free WiFi
Luxury couple's country retreat in spectacular location in the North York Moors

Cottage in glaisdale

Luxury couple's country retreat in spectacular location in the North York Moors
10.0 out of 10, Exceptional, (93)
"Property was immaculate. Mark and Moira.where amazing, went way over and above without being asked. We would recommend this wee star of a place to anyone. Views are amazing, and the peace and quiet, just wow. "
United Kingdom
Pau K.
$393 nightly
The price is $393
Jan 5 - Jan 6, 2026
Total with taxes and fees
Luxury couple's country retreat in spectacular location in the North York Moors
2 bedrooms, desk, iron/ironing board, travel crib
2 Bedroom House with Garden next to the River Tees

Vacation Home in Stockton on Tees

2 Bedroom House with Garden next to the River Tees
10.0 out of 10, Exceptional, (2)
"Good location, host was very responsive, property had everything we needed. Good check-in/out process "
United Kingdom
David R.
$119 nightly
The price is $119
Jan 5 - Jan 6, 2026
Total with taxes and fees
2 Bedroom House with Garden next to the River Tees
Living area
2 bedroom accommodation in Pickering

Cottage in Pickering

2 bedroom accommodation in Pickering
9.0 out of 10, Wonderful, (8)
"Most enjoyable, well appointed cottage comfortable central to the town. Plenty to do and see with the railway nearby. We are looking forward to coming back next year. The Young family. "
United Kingdom
Sonia Y.
$284 nightly
The price is $284
Jan 23 - Jan 24, 2026
Total with taxes and fees
2 bedroom accommodation in Pickering
Cottage | Interior
Ghyll Cottage

Cottage in Pickering

Ghyll Cottage
3.5 star property
$340 nightly
The price is $408
Jan 6 - Jan 7, 2026
Total with taxes and fees
Ghyll Cottage
Exterior
Old Mill Tiny Homes

Aparthotel in Yarm

Old Mill Tiny Homes
2.0 star property
$132 nightly
The price is $159
Jan 5 - Jan 6, 2026
Total with taxes and fees
Old Mill Tiny Homes
Interior
Luxury retreat for 2 couples/ family in spectacular location in North York Moors

Vacation Home in Glaisdale

Luxury retreat for 2 couples/ family in spectacular location in North York Moors
10.0 out of 10, Exceptional, (42)
"Loved the location and the property was lovely. We would return again!"
United States
Cynthia T.
$535 nightly
The price is $535
Dec 30 - Dec 31
Total with taxes and fees
Luxury retreat for 2 couples/ family in spectacular location in North York Moors
Interior
4 bedroom accommodation in Goathland

Cottage in Goathland

4 bedroom accommodation in Goathland
8.0 out of 10, Very Good, (1)
"Will definitely go back again my family loved it had a power cut made it more adventurous loved every minute off it neighbours across the way gave us some candles next day didn't use them but people made you welcome"
United States
Fredrick Dobbs
$692 nightly
The price is $692
Jan 10 - Jan 11, 2026
Total with taxes and fees
4 bedroom accommodation in Goathland
Exterior detail
2 bedroom accommodation in Robin Hoods Bay

Cottage in Robin Hoods Bay

2 bedroom accommodation in Robin Hoods Bay
9.2 out of 10, Wonderful, (10)
"Lovely quaint walk through several levels of walkways and beautuful traditional cottages. Tucked away surrounded by cottage gardens. Like stepping back in time. Beautiful weather surprisingly. Lovely friendly people. Shops and places to eat and drink , within 5 mins through the street's. Very steep hill and steps add to rhe charm of the winding roads down to the bay front. Photographers heaven. 4th time here over the years with small changes to eateries. "
United Kingdom
Dawn W.
$604 nightly
The price is $604
Dec 27 - Dec 28
Total with taxes and fees
2 bedroom accommodation in Robin Hoods Bay
Cottage, Private Bathroom | 2 bedrooms
Clarence Cottage

Cottage in Whitby

Clarence Cottage
4.0 star property
10.0 out of 10, Exceptional, (14)
"Excellent stay "
United Kingdom
MICHAEL
$169 nightly
The price is $203
Jan 7 - Jan 8, 2026
Total with taxes and fees
Clarence Cottage
Studio | Dining
Courtyard Rooms - Studio - Double Bed - Wifi

Apartment in Northallerton

Courtyard Rooms - Studio - Double Bed - Wifi
3.0 star property
8.0 out of 10, Very Good, (2)
"Very friendly reception from the landlord Gareth who provided a most enlivening atmosphere in the Duke of Wellington ie a darts match for the men and Easter wreath making for the ladies. No food unfortunately but we found an excellent Italian restaurant in nearby Northallerton. The courtyard room was clean and comfortable, marred only by a very awkward shower - not easy to enter, due to lack of space."
United Kingdom
Alison
$106 nightly
The price is $106
Jan 4 - Jan 5, 2026
Total with taxes and fees
Courtyard Rooms - Studio - Double Bed - Wifi
Cottage | Interior
5 Church View

Cottage in Pickering

5 Church View
3.5 star property
10.0 out of 10, Exceptional, (1)
$377 nightly
The price is $452
Dec 28 - Dec 29
Total with taxes and fees
5 Church View
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 Castleton Hotel Reviews

Cross Keys Hotel by Greene King Inns

Cross Keys Hotel by Greene King Inns

10/10 Excellent
"Great food and great service"
liam 1-night trip
Posted 4 days ago
Cross Keys Hotel by Greene King Inns

Find out more about Castleton

Everything you need to know about Castleton 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 Castleton 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 Castleton vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castleton vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castleton. 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 Castleton 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 $109 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 Castleton rentals

At Expedia, we put the best Castleton 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 Castleton 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 Castleton 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 Castleton. 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 Castleton?

Yes, we give you a choice of vacation rentals near popular attractions in Castleton, or you can select a more secluded option if you're looking for a relaxing stay. Castleton is known for its parks.

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

Skipton Lodge: You might want to consider this vacation home rental near Castleton, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

What can I see and do in Castleton?

Explore the area and family-friendly sights such as The Moors National Park Centre, or get out into nature at a spot like North York Moors National Park. In the larger area, you’ll find Danby Castle and Roseberry Topping.

What are vacation rentals like in Castleton?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Castleton. Vacation rentals feature amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for a family getaway.