A field of wheat with a tower in the background.

Winterslow Holiday Rentals

Q: What are some of the best holiday rentals that Winterslow has to offer?

Unique waterside home in stunning location. : This holiday home rental outside of Winterslow is located on the waterfront, and has a balcony, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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Dates

November 2026

December 2026

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Our top choices for Winterslow holiday rentals

A sign for Hotel Peartree, a serviced apartment, with contact information and website.

1. Peartree Serviced Apartments

Salisbury

Stephanie

includes taxes & fees

8 Nov - 9 Nov

A tent with a bed inside, a colorful rug, and a sign on the ground.

2. Stone Circle Glamping

Durrington

Darnell

includes taxes & fees

8 Nov - 9 Nov

A living room with a dark blue sofa, a round wooden coffee table, a dining table with chairs, a large abstract painting, a round mirror, and a window with curtains.

3. Charles Hope Salisbury Centre

Salisbury

Theodros

includes taxes & fees

16 Nov - 17 Nov

A brick building with a dark wooden door, two windows, and a bench in front.

4. The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.

Clarendon

includes taxes & fees

15 Nov - 16 Nov

A modern living room with two sofas, a coffee table, and a Christmas tree.

5. The Coach House Apartment — Stylish Loft Retreat for up to 4 ppl.

Clarendon

includes taxes & fees

15 Nov - 16 Nov

A wooden house with a sloped roof, a glass door entrance, and a patio area with outdoor furniture.

6. The Old Stables — Wiltshire Countryside Cottage for up to 6 ppl.

Clarendon

includes taxes & fees

8 Nov - 9 Nov

A spacious living area with a high ceiling, wooden beams, a large TV, and a dining area with a table and chairs.

7. The Summer House — Unique Hilltop Retreat for up to 4 ppl.

Salisbury

includes taxes & fees

8 Nov - 9 Nov

A conservatory with a dining area, a wooden table, and chairs.

8. Cozy & Self Contained The Garden Annex 306

Salisbury

Dala B.

includes taxes & fees

9 Nov - 10 Nov

A modern interior with a red sofa, black chairs, and a patterned floor.

9. Second Nature Southampton

Southampton City Centre

Gary

includes taxes & fees

6 Dec - 7 Dec

A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a radiator.

10. Settle Winchester

Winchester City Center

includes taxes & fees

8 Nov - 9 Nov

A bedroom with a wooden door, a bed with a beige and white striped bedspread, a fluffy beige throw blanket, and a pink pillow. There are framed pictures on the wall and a window with curtains.

The Polygon

includes taxes & fees

7 Nov - 8 Nov

A traditional brick house with a gabled roof, surrounded by lush greenery and flowering plants.

15. Beautiful, traditional rural cottage

Shrewton

Michael

includes taxes & fees

23 Nov - 24 Nov

A brick house with a large front porch, a dining table set up outside, and a well-maintained lawn.

16. Bridge Farmhouse

Salisbury

Jennifer E

includes taxes & fees

30 Nov - 1 Dec

A traditional thatched-roof cottage with a brick extension, a white door, and a small window.

17. 1 bedroom accommodation in Burgate, near Fordingbridge

Burgate, near Fordingbridge

Angela Horn

includes taxes & fees

16 Nov - 17 Nov

A living room with a sofa, armchairs, a coffee table, and a lamp.

18. Elm Tree House - UK51762

Landford, near Salisbury

includes taxes & fees

9 Nov - 10 Nov

A modern living room with a flat-screen TV displaying 'NETFLIX,' a potted plant, a painting on the wall, and a window with curtains.

19. 2BR Flat in Andover | Near Local Amenities

Hampshire

includes taxes & fees

8 Nov - 9 Nov

A conservatory with a glass ceiling, a cushioned seating area, and various potted plants.

20. Annie’s House in Amesbury

Amesbury

includes taxes & fees

7 Nov - 8 Nov

View all properties

Find holiday rentals that suit your style

Top Winterslow Hotel Reviews

A row of traditional brick houses with a grassy lawn and a canal in the foreground.

The Riverside, WorldHotels Distinctive

Salisbury

10/10 Excellent

The Riverside is close to the centre of Salisbury but still easy to get to, no narrow streets and plenty of easy parking. The river view room was modern, clean, comfortable and very pleasant. The access to the garden and the river bank was a real plus. The breakfast buffet was good, fill up here and you will barely need lunch! The only minor problem is that the gravel on the car park isn't friendly to wheeled suitcases.

Sadie

A window with a view of a cityscape, including a prominent tower.

Sarum College

Salisbury

10/10 Excellent

David

A cozy restaurant with a bar area, wooden tables, and a mural on the wall.

The Duke on The Test

Romsey

10/10 Excellent

Kenneth

Find out more about Winterslow

Everything you need to know about Winterslow holiday rentals

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

Winterslow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winterslow. 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 depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winterslow holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winterslow holiday rentals we have selected for you start as low as AU$103 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winterslow rentals

At Expedia, we put the best Winterslow holiday 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 Winterslow 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 Winterslow holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winterslow. 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 holiday rentals in Winterslow?

Yes, there are holiday rentals close to the most popular sights in Winterslow, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winterslow has to offer?

Unique waterside home in stunning location.: This holiday home rental outside of Winterslow is located on the waterfront, and has a balcony, a garden and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Winterslow?

Explore the area and family-friendly sights such as Paultons Family Theme Park - Home of Peppa Pig World, or get out into nature at a spot like New Forest National Park. In the wider area, you’ll find Southampton Cruise Terminal and Boscombe Down Aviation Collection.

What’s a holiday rental in Winterslow like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winterslow. Holiday rentals provide amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies packed with people while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive option for a small group gathering.

Winterslow Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winterslow holiday rentals

1. Peartree Serviced Apartments

2. Stone Circle Glamping

3. Charles Hope Salisbury Centre

4. The Carriage House — Wiltshire Countryside Cottage for up to 6 ppl.

5. The Coach House Apartment — Stylish Loft Retreat for up to 4 ppl.

6. The Old Stables — Wiltshire Countryside Cottage for up to 6 ppl.

7. The Summer House — Unique Hilltop Retreat for up to 4 ppl.

8. Cozy & Self Contained The Garden Annex 306

9. Second Nature Southampton

10. Settle Winchester

11. The Bike Shed

12. Farm Cottage on a Secluded 9-acre Equestrian Small Holding

13. Beautiful New Forest Hideaway

14. Coventry Road Apartments Flat 1

15. Beautiful, traditional rural cottage

16. Bridge Farmhouse

17. 1 bedroom accommodation in Burgate, near Fordingbridge

18. Elm Tree House - UK51762

19. 2BR Flat in Andover | Near Local Amenities

20. Annie’s House in Amesbury

Find holiday rentals that suit your style

Top Winterslow Hotel Reviews

The Riverside, WorldHotels Distinctive

10/10 Excellent

Find out more about Winterslow

Winterslow holiday rentals: An excellent choice for every season

How to find incredible deals on Winterslow rentals

Frequently Asked Questions

Can I find holiday rentals in Winterslow?

What are some of the best holiday rentals that Winterslow has to offer?

What’s there to see and do in Winterslow?

What’s a holiday rental in Winterslow like?