Cheselbourne Vacation Rentals from CA $267: Short-Term Rentals for 2026

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Our top choices for Cheselbourne vacation rentals

A traditional stone building with a green door, two windows, and a sign reading "The Old School House."

1. The Old School House

Dorchester

NIGEL

CA $1,064 total

includes taxes & fees

Oct 15 - Oct 16

A small wooden structure with a door and steps leading up to it, surrounded by greenery and a picnic table with cushions.

2. 1 bedroom accommodation in Ibberton, Blandford Forum

Ibberton, Blandford Forum

Paul Mitchell

CA $297 total

includes taxes & fees

Oct 10 - Oct 11

A cozy room with exposed brick walls, wooden beams, and a mix of leather and fabric seating.

3. The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

Winterborne Whitechurch

"Excellent cottage! Super quirky and perfect for a large group. My husband’s family all met at the Langham vineyard (jut 8 minute’s drive up the road from the accommodation) to celebrate his 50th ; adults, kids, dog…we had a wonderful time and carried on the celebrations with an evening of chat in the comfortable lounge and some food in the spacious dining area before heading to bed (all 10 of us). Martin was a wonderful host, very quick responses and super accommodating. The whole area is...

Stacia B.

CA $719 total

includes taxes & fees

Oct 26 - Oct 27

A picnic table in a grassy area with a wooden fence and trees in the background.

4. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

Glanvilles Wootton, near Sherborne

Caroline H.

CA $797 total

includes taxes & fees

Oct 14 - Oct 15

A beach with a natural rock arch formation.

5. Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

Wool

Kristina

CA $511 total

includes taxes & fees

Oct 12 - Oct 13

A dining area with a round table, wicker chairs, and a view of boats at a marina.

6. Classic Yacht Nadine with Hot Tub, Poole Harbour Bay

Poole

Lesley-Anne W.

CA $634 total

includes taxes & fees

Oct 7 - Oct 8

A bathroom with a window, a sink, and two potted plants.

7. Hardy View Farm House

Dorchester

Carol S.

CA $338 total

includes taxes & fees

Oct 26 - Oct 27

A modern kitchen with a dining table set for two, featuring a white plate, a bowl, a wine glass, and a decorative centerpiece.

8. ⭐⭐⭐⭐⭐ Super Cool Apartment Parking, Netflix & WiFi

Parkstone

Hannah L.

CA $291 total

includes taxes & fees

Oct 5 - Oct 6

A stone house with a red-tiled roof, surrounded by a pond with reflections and greenery.

9. 2 bedroom accommodation in Goathill, near Sherborne

Goathill, near Sherborne

Jill Leeson

CA $605 total

includes taxes & fees

Oct 15 - Oct 16

A modern outdoor patio with wicker furniture and a glass door leading to a covered area.

10. Private Luxury By The Sea

Poole

Luke

CA $267 total

includes taxes & fees

Oct 4 - Oct 5

A rustic kitchen with wooden beams, a stone wall, a sink, a stove, and a washing machine.

11. Way's Forge

Dorchester

Virginia

CA $973 total

includes taxes & fees

Oct 6 - Oct 7

A beach with people, a large striped tower, and buildings in the background.

12. The Sailors Studio|Sleeps2|Weymouth Beach|

Weymouth Town Center

CA $253 total

includes taxes & fees

Oct 4 - Oct 5

A living room with a sofa, a coffee table, a bookshelf, and a mounted TV.

13. Super Trendy Apartment - Free Parking & Fast WiFi

Poole Old Town

Tim H.

CA $252 total

includes taxes & fees

Oct 4 - Oct 5

A modern hotel room with a bed, a black tray with pastries, a window with a view, and a wall-mounted shelf with a plant.

14. Stylish modern retreat overlooking Poole Quay

Poole

David R.

CA $313 total

includes taxes & fees

Oct 4 - Oct 5

A modern living room with a brick wall, a dining area with a table and chairs, and a sofa.

15. Modern Apartment -Parking & WiFi

Poole Old Town

Paul

CA $231 total

includes taxes & fees

Oct 6 - Oct 7

A bedroom with a large mirror, a bed, a chair, and a window with curtains.

16. Beautiful Couples Retreat - FREE Parking & WiFi

Poole Old Town

Frazer

CA $319 total

includes taxes & fees

Oct 11 - Oct 12

A modern living room with a sofa, coffee table, and a kitchen area with a washing machine.

17. Streamside Apartments

Yeovil

Anonymous traveller

CA $190 total

includes taxes & fees

Oct 4 - Oct 5

A modern living room with a grey sofa, yellow cushions, a yellow rug, and a large window with curtains.

18. Brand NEW 3 bedroom house - garden & parking +wifi

Poole

James

CA $317 total

includes taxes & fees

Oct 7 - Oct 8

A two-story building with a blue storefront labeled "The Dorsel Store."

19. A spacious, well equipped private annexe with garden and parking in Shaftesbury.

Shaftesbury Dorset

Martin K.

CA $221 total

includes taxes & fees

Oct 4 - Oct 5

A room with a round mirror reflecting a living area, including a sofa, a lamp, and a window with curtains.

20. Stunning 2 bedroom Apartment inc. Free Parking

Poole Old Town

Luke W.

CA $295 total

includes taxes & fees

Oct 6 - Oct 7

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Top Cheselbourne Hotel Reviews

Haven Hotel

8/10 Good

"Lovely location if you like to hear the waves at night. Good breakfast."

Fairhaven Hotel

10/10 Excellent

"Corridors have sensor lights, some of which take a while to light up so it can be dark. Housekeeping was fab with clean towels and refreshments replaced every day. Excellent beach front location. Our room this time was on the 2nd floor with a lovely bay window. We have also stayed in the 1st floor room directly below, both are great rooms. Car parking was heavily discounted at an excellent price."

Find out more about Cheselbourne

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

Cheselbourne vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheselbourne. 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 Cheselbourne 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 Cheselbourne vacation rentals we have selected for you start as low as CA $267 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cheselbourne rentals

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

Yes, we offer vacation rentals close to the most popular sights in Cheselbourne, or you can choose a more remote option if you're looking for a relaxing stay. Our travelers say Cheselbourne has a good selection of restaurants. Make sure you have time to check out the bars while you're in the area.

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

Classic Holiday Home for 6, relaxing family getaway near Durdle Door: This vacation home rental outside of Cheselbourne comes with WiFi so you can feel at home during your trip. Kitchen amenities include a fridge, a stovetop, and a microwave.

What’s there to see and do in Cheselbourne?

While exploring the area, visit family-friendly sights like Monkey World Ape Rescue Center, or get outside and enjoy nature at Osmington Bay Beach. Cerne Abbas Giant and Tutankhamun: The Exhibition are a couple of places you'll find in the larger area.

What’s a vacation rental in Cheselbourne like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Cheselbourne. Vacation rentals feature extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for a small group gathering.

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Check prices for these dates

Our top choices for Cheselbourne vacation rentals

1. The Old School House

2. 1 bedroom accommodation in Ibberton, Blandford Forum

3. The Old Police House, sleeps 10, 1850,s cottage, Family Stay!

4. 2 bedroom accommodation in Glanvilles Wootton, near Sherborne

5. Family home close to Lulworth Cove, Durdle Door, The Tank Musuem & Monkey World

6. Classic Yacht Nadine with Hot Tub, Poole Harbour Bay

7. Hardy View Farm House

8. ⭐⭐⭐⭐⭐ Super Cool Apartment Parking, Netflix & WiFi

9. 2 bedroom accommodation in Goathill, near Sherborne

10. Private Luxury By The Sea

11. Way's Forge

12. The Sailors Studio|Sleeps2|Weymouth Beach|

13. Super Trendy Apartment - Free Parking & Fast WiFi

14. Stylish modern retreat overlooking Poole Quay

15. Modern Apartment -Parking & WiFi

16. Beautiful Couples Retreat - FREE Parking & WiFi

17. Streamside Apartments

18. Brand NEW 3 bedroom house - garden & parking +wifi

19. A spacious, well equipped private annexe with garden and parking in Shaftesbury.

20. Stunning 2 bedroom Apartment inc. Free Parking

Find vacation rentals that suit your style

Top Cheselbourne Hotel Reviews

Haven Hotel

Fairhaven Hotel

The Knoll House

The Jubilee Hotel East- with Spa Facilities

Sandbanks Hotel

Holiday Inn Express Poole by IHG

Sleeping Bear Hotel Dorchester

Hotel du Vin & Bistro Poole

George Albert Hotel & Spa

Find out more about Cheselbourne

Frequently asked questions

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