A gravel path leading to a gated entrance surrounded by lush greenery and a brick wall.

Search Holiday Rentals in Middle Winterslow

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

7 bedroom, Stunning Cottage with Hot-Tub & Cinema Room : This holiday home rental outside of Middle Winterslow is in a rural location, and equipped with a Smart TV and free WiFi to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, 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 Middle Winterslow holiday rentals

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

1. Stone Circle Glamping

Durrington

Darnell

includes taxes & fees

13 Nov - 14 Nov

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

2. Peartree Serviced Apartments

Salisbury

Stephanie

includes taxes & fees

15 Nov - 16 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

23 Nov - 24 Nov

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

4. Cozy & Self Contained The Garden Annex 306

Salisbury

Dala B.

includes taxes & fees

23 Nov - 24 Nov

A bedroom with a bed, a chair, a wardrobe, and a radiator.

5. Coventry Road Apartments Flat 1

The Polygon

includes taxes & fees

12 Nov - 13 Nov

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

6. Settle Winchester

Winchester City Center

includes taxes & fees

19 Nov - 20 Nov

A modern kitchen with dark cabinetry, a dining area with a wooden table and metal chairs, and a living room with a blue sofa and a green plant.

7. 1BR Flat in Andover | Near Local Amenities

Hampshire

includes taxes & fees

15 Nov - 16 Nov

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

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

Clarendon

includes taxes & fees

12 Nov - 13 Nov

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

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

Clarendon

includes taxes & fees

12 Nov - 13 Nov

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

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

Clarendon

includes taxes & fees

12 Nov - 13 Nov

A compact living space with a kitchen, dining area, and a TV.

11. Bright And Airy Cottage Close To Salisbury Centre

Salisbury

includes taxes & fees

27 Nov - 28 Nov

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

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

Salisbury

includes taxes & fees

15 Nov - 16 Nov

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

13. Beautiful, traditional rural cottage

Shrewton

Michael

includes taxes & fees

23 Nov - 24 Nov

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

14. Second Nature Southampton

Southampton City Centre

Yahong Susan

includes taxes & fees

13 Nov - 14 Nov

An outdoor patio with a brick wall, a grill, wicker furniture, and a dining table.

15. Beautiful New Forest Hideaway

West Wellow

Alena M.

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with a dining table, chairs, and a stainless steel range hood.

16. 1BR Flat in Andover | Near Local Amenity

Hampshire

includes taxes & fees

15 Nov - 16 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.

17. The Bike Shed

Romsey

includes taxes & fees

23 Nov - 24 Nov

A row of wooden cabins with attached porches, each with a small porch light.

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

Salisbury

Diana T.

includes taxes & fees

12 Nov - 13 Nov

A cozy tented accommodation with a bed, bedside tables, a lamp, a laptop, and a potted plant.

19. The Leaf & Lantern Dome - Sleeps 5 - Dog Friendly

Pewsey

includes taxes & fees

15 Nov - 16 Nov

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

20. Bridge Farmhouse

Salisbury

Jennifer E

includes taxes & fees

30 Nov - 1 Dec

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Find holiday rentals that suit your style

Top Middle 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

Jason

A restaurant with brick walls, wooden tables, and hanging spherical light fixtures.

The Fox

Winchester

10/10 Excellent

David

A traditional room with exposed wooden beams, a fireplace, and classic furniture.

The Old House Guesthouse

Salisbury

10/10 Excellent

Location was on a busy main road so exiting by car was difficult at times. Car parking although off road was tight. A bit too far to walk into Salisbury for an evening meal and nothing close by was good enough. Breakfast was hot and excellent, many choices. Staff very friendly. A very distinguished property with quiet rooms, no squeaky floorboards as we have seen and heard elsewhere. A lovely place and would stay again.

Mike

A breakfast setting with a variety of dishes, including bowls of cereal, croissants, and orange juice.

The Pembroke Arms

Salisbury

10/10 Excellent

A lovely stay at the Pembroke Arms. There was plenty of free parking to the rear of the Inn. Reception was efficient and friendly. Our room - two double beds so for four people - was large and comfortable with lovely touches like TeaPig teas and ground coffee. The room itself was quite cold but reception turned the heating up for us and it was a really cold day so no complaints. We ate in the hotel that evening - a really nice restaurant and delicious (massive) pies. Breakfast was one of the...

Andrew

A dining area with wooden tables and chairs, a fireplace, and a stone wall.

The Palmerston Rooms

Romsey

10/10 Excellent

Paul

A modern building with a curved facade, large windows, and a well-lit entrance area.

Holiday Inn Salisbury - Stonehenge by IHG

Salisbury

10/10 Excellent

Louise

A table with a drink and a vase of flowers, a window with a view of a stone building.

The Chapter House

Salisbury

10/10 Excellent

Lorraine

A breakfast setup with a table, breakfast items, and a brick wall background.

The Dog and Gun

Salisbury

10/10 Excellent

Martin

A cozy living room with a fireplace, a bar area, and a dining space.

The Woodfalls Inn

Salisbury

10/10 Excellent

Our visit was just overnight. The location of Woodfalls Inn was perfect for us as we visited people/places in Southampton, Salisbury and Fordingbridge. Perfect if you are visiting the New Forest. Everything in the hotel felt new and pristine. The room was very comfortable. Breakfast was very good. The price was very competitive compared to other places we looked at in the area. Certainly one we will remember for when we are next down that way.

Andrew

A man sitting at a table in a cafe with hanging plants, wooden furniture, and a bar in the background.

The Cromwell Arms

Romsey

10/10 Excellent

Julie

A view through a window with a metal frame and a wooden fence.

Thorps Farm Bed and Breakfast

Fordingbridge

10/10 Excellent

Sue

A cozy loft apartment with a dining area, a sofa, a TV, and skylights.

New Forest Lodge

Salisbury

10/10 Excellent

BalletLeanne

A restaurant with a glass ceiling, wooden tables and chairs, and a view of the outdoors.

The Three Cups Inn

Stockbridge

10/10 Excellent

My brother and I walk together once a year to catch up as we live in different parts of the country. This year we decided on the 24 mile Clarendon Way from Winchester to Salisbury. Although off the Way Stockbridge is a beautiful village and convenient half way point to stop for the night. On arrival at the Three Cups very tired after our twelve mile walk we were shown to two very pleasant rooms by a helpful member of staff. The rooms were clean and fresh with very welcome tea and biscuits...

Andrew

A cozy room with a wooden bench, a sofa, and a table with a glass display case.

The White Horse Hotel, Romsey, Hampshire

Romsey

10/10 Excellent

Stephen

The Great Bustard

Salisbury

10/10 Excellent

Simon

Find out more about Middle Winterslow

Everything you need to know about Middle 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 Middle Winterslow holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 Middle Winterslow holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middle Winterslow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middle 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 depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middle 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 Middle Winterslow holiday rentals we have selected for you start as low as £60 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Middle Winterslow rentals

At Expedia, we put the best Middle 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 Middle 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 Middle 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 Middle 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

Are there holiday rentals in Middle Winterslow?

Yes, there are holiday rentals close to the most popular sights in Middle 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 Middle Winterslow has to offer?

7 bedroom, Stunning Cottage with Hot-Tub & Cinema Room: This holiday home rental outside of Middle Winterslow is in a rural location, and equipped with a Smart TV and free WiFi to help you feel perfectly comfortable in your new surroundings. It has 7 bedrooms, as well as a kitchen with a dishwasher, a fridge and an oven, so that you can cook with friends or family.

What can I see and do in Middle Winterslow?

While exploring the area, visit family-friendly sights like Paultons Family Theme Park - Home of Peppa Pig World, or get outside and enjoy nature at New Forest National Park. In the wider area, you’ll find Boscombe Down Aviation Collection and Market Square.

What are holiday rentals like in Middle Winterslow?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middle Winterslow. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for a family getaway.

Search Holiday Rentals in Middle Winterslow

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Middle Winterslow holiday rentals

1. Stone Circle Glamping

2. Peartree Serviced Apartments

3. Charles Hope Salisbury Centre

4. Cozy & Self Contained The Garden Annex 306

5. Coventry Road Apartments Flat 1

6. Settle Winchester

7. 1BR Flat in Andover | Near Local Amenities

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

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

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

11. Bright And Airy Cottage Close To Salisbury Centre

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

13. Beautiful, traditional rural cottage

14. Second Nature Southampton

15. Beautiful New Forest Hideaway

16. 1BR Flat in Andover | Near Local Amenity

17. The Bike Shed

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

19. The Leaf & Lantern Dome - Sleeps 5 - Dog Friendly

20. Bridge Farmhouse

Find holiday rentals that suit your style

Top Middle Winterslow Hotel Reviews

The Riverside, WorldHotels Distinctive

10/10 Excellent

Find out more about Middle Winterslow

Middle Winterslow holiday rentals: An excellent choice for every season

How to find incredible deals on Middle Winterslow rentals

Frequently Asked Questions

Are there holiday rentals in Middle Winterslow?

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

What can I see and do in Middle Winterslow?

What are holiday rentals like in Middle Winterslow?